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Дисертації з теми "Carbohydrates"

Автор: Grafiati

Опубліковано: 4 червня 2021

Оновлено: 7 вересня 2024

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1

Drinnan, Nicholas Barry. "Towards the synthesis of biologically active carbohydrates and carbohydrate mimetics /." [St. Lucia, Qld], 2004. http://www.library.uq.edu.au/pdfserve.php?image=thesisabs/absthe18237.pdf.

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2

Hill, Anthony David. "Computational methods in the study of carbohydrates and carbohydrate-active enzymes." [Ames, Iowa : Iowa State University], 2006.

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3

Scaffidi, Adrian. "Synthetic endeavours in carbohydrates." University of Western Australia. School of Biomedical, Biomolecular and Chemical Sciences, 2007. http://theses.library.uwa.edu.au/adt-WU2007.0114.

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The overwhelming occurrence and structural diversity of carbohydrates in Nature indicate their importance in a range of fundamental life processes. Indeed, it is this diversity that has lead to the two equally diverse groups of carbohydrate-processing enzymes, namely the glycoside hydrolases and glycosyl transferases. Thus, understanding the role of both carbohydrates and their processing enzymes in biological systems has attracted significant attention. This thesis, firstly, describes endeavours towards the synthesis of an inositol ?- amino acid, along with a series of sugar α-substituted carboxylic acid esters, utilising an extension of the modified Corey-Link reaction. The emphasis of the thesis is then shifted towards the synthesis of a putative inhibitor of a family GH26 lichenase from Clostridium thermocellum (CtLic26A). The preparation of 2-deoxy-2-fluoro-β-laminarbiosyl fluoride 1 is described, along with elaboration into oligosaccharides utilising AbgE358G glycosynthase technology. Crystallographic investigations indicated that the transition state adopted by CtLic26A is in stark contrast to that utilised by the related family GH26 mannanase from Pseudomonas cellulose (Man26A). ... Following on from this work, expanding the role of the AbgE358G glycosynthase acceptor repertoire to accommodate inositol substrates was explored, furthering the synthetic utility of this enzyme. Thus, a number of inositol acceptors bearing an aryl anchor, for example 2, were prepared and shown to be surrogates for carbohydrate acceptors. ... The thesis then describes the synthesis of an acetamide derivative of 1-epivalienamine, namely 3, a putative inhibitor of β-N-acetylglucosaminidases. Both the synthesis of 3, along with kinetic data for four β-N-acetylglucosaminidases, is reported; as well, Western blot analysis indicated no inhibition of a recombinant OGTase. ... Related to the preparation of a putative inhibitor of β-N-acetylglucosaminidases was the synthesis of a conformationally rigid carbocycle derivative of PUGNAc 4, along with two other derivatives 5 and 6. These compounds were also tested against four β-N-acetylglucosaminidases and a recombinant OGTase. ... Finally, the synthesis of a mechanism-based inhibitor of family GH3 β-Nacetylglucosaminidases, namely 2-acetamido-2-deoxy-5-fluoro-β-D-glucopyranosyl fluoride 7, is described. The incorporation of an azido moiety allows for the utilisation of 8 as an effective probe of β-N-acetylglucosaminidases. ...

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4

Smith, Paul W. "Carbohydrates in synthesis." Thesis, University of Oxford, 1986. https://ora.ox.ac.uk/objects/uuid:97dd273b-2577-4556-8889-361f801a826a.

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The use of carbohydrates as starting materials for organic synthesis is illustrated by the synthesis of several polyhydroxylated piperidine, pyrrolidine, indolizine and pyrrolizidine alkaloids. Nucleophilic displacement by azide ion at C-2 in a D-glucose derivative, with subsequent intramolecular cyclisation through nitrogen onto the C-6 or C-5 position and functional group manipulation, led to the synthesis of: 1,5-dideoxy-1,5-imino-D-mannitol; 1,2,5-trideoxy-1,5-imino-D-arabinohexitol; 1,5-dideoxy-1,5-imino-D-glucitol; 2-Acetamido-1,5-imino-1,2,5- trideoxy-D-glucitol; 2-Acetamido-1,5-imino-1,2,5-trideoxy-D-mannitol; (2S, 3R, 4R, 5S)-3,4,5-trihydroxypipecolic acid; (2S, 3R, 4R, 5R)-3,4,5- trihydroxypipecolic acid and 2,5-dideoxy-2,5-imino-D-mannitol. Nucleophilic displacement by azide ion at C-3 in a D-glucose derivative, with subsequent intramolecular cyclisation through nitrogen onto the C-6 position, produced the tosylate salt of 3,6-dideoxy-3,6-imino-1,2-0-isopropylidene- â«-D-glucofuranose, a highly divergent intermediate, from which the pyrrolidines: 1,4-dideoxy-1,4-imino-L-gulitol, 1,4-dideoxy-1,4-imino-D-lyxitol and (2S, 3S, 4R) - 3,4-dihydroxyproline were prepared directly. Periodate cleavage of the C1-2 bond and a 2-C chain extension from C-2 with subsequent intramolecular cyclisation, produced the pyrrolizidine (IS, 2R, 8R) - 1,2-dihydroxypyrrolizidine. An intramolecular Wadsworth Emmans cyclisation between a lactol at C-1 and a phosphonate, produced by a DCC coupling of the amine with dimethoxyphosphinylacetic acid, led to the formation of the indolizine (1S, 2R, 8S, 8aR) - 1,2,8-trihydroxyoctahydroindolizine. The synthesis of 1,4-dideoxy-1,4-imino-D-lyxitol, was achieved by connection of C1 and C4 of a D-mannose derivative through nitrogen. Methyl 3,5-0-isopropylidene- â«-D-xylofuranoside was elaborated to both enantiomers of 1,4-dideoxy-1,4-imino-arabinitol. The _D-enantiomer was produced by introduction of a nitrogen between C-2 and C-5, the L- enantiomer by introduction of a nitrogen between C-1 and C-4. (2R, 3S, 4R) - 3,4-dihydroxyproline was prepared from _D-ribonolactone. The key step of the synthesis was a nucleophilic displacement by azide ion at C-2 in which the stereochemistry was unexpectedly retained.

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5

Wilson, Francis X. "Carbohydrates in synthesis." Thesis, University of Oxford, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.280014.

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6

Hotchkiss, David J. "Studies on branched carbohydrates." Thesis, University of Oxford, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.442450.

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7

Homan, Christopher David. "Phosphorus derivatives of carbohydrates." Thesis, University of Newcastle Upon Tyne, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.239564.

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8

Laventine, Dominic. "Hetero-annulation of carbohydrates." Thesis, University of Leicester, 2006. http://hdl.handle.net/2381/29981.

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The aim of the research to be undertaken is the synthesis of hetero-annulated glucose derivatives. In particular the synthesis of five-, six-, and seven- and eight-membered N-containing fused heterocycles is desired, with the nitrogen attached at the C-2 and C-3 position of the sugar ring. Emphasis is placed upon using the sugar ring as a scaffold to enable diastereoelective synthesis. A variety of synthetic techniques are to be employed to achieve ring-closure, especially reductive lamination, ring-closing metathesis and photochemical methods of annulation. (Fig. 9206A).;Such compounds could be useful as precursors to alkaloid synthesis due to the huge range of methods for the conversion of pyranosides to other ring systems. In addition, previous work has shown that such compounds have an inhibitory effect on glycoside processing enzymes. The pyrollidines synthesised have been tested as Glycosidase inhibitors, and some have been shown to be weak specific beta-Galactosidase inhibitors.;Using similar techniques as those employed to produce the lactam above, 2,O- and 3,O-fused lactones were also produced, with dimerised by-products also isolated. Intramolecular photocyclisation was also employed to produce complex multicyclic fused carbocyles. (Fig. 9206B).;Synthesis of N-linked amino sugar dimers was also achieved, and initial attempts at deprotection made. (Fig. 9206C).

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9

Dhamjewar, R. "Synthesis of complex carbohydrates." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 1991. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/3004.

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10

Reddy, G. V. "Synthesis of complex carbohydrates." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 1990. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/2975.

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11

Jordaan, Michelle Bernitta. "Effect of processing on the starch and glycemic properties of Digitaria spp." Thesis, Cape Peninsula University of Technology, 2013. http://hdl.handle.net/20.500.11838/2024.

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Thesis (MTech (Food Technology))--Cape Peninsula University of Technology, 2013.
Acha starch was isolated and purified from clean and milled acha grain. Functional, thermal and physicochemical properties of acha starch were analysed using appropriate methods. Wheat starch was used as the reference standard. Acha bread from acha grain was baked and the consumer sensory acceptability was evaluated and white wheat bread was used as the reference standard. The effect of baking, boiling, steaming and microwaving on the starch and glycemic properties of the acha starch was evaluated. With regard to thermal properties, gelatinisation temperature of acha and iburu starches typifies that of waxy starch. Acha starch has similar retrogradation temperature profiles as that of wheat. There were however significant differences in some of the functional properties (pasting and turbidity) and physico-chemical properties (in vitro starch digestibility), but no significant difference in the texture profile analysis (TPA) and water binding capacity (WBC). WBC of both acha varieties was higher than that for wheat starch. Due to its high break down viscosity, white acha starch can be included in foods that are subjected to high temperature processing. This indicates that both acha starch varieties can be used for hot and cold desserts as well as for soft jelly like sweets and confectionery toppings. A prescreening exercise using carboxymethyl cellulose (CMC), Xanthan gum, yeast and acha starch as the variables was successful in concluding a recipe which rendered acha bread with the optimum specific loaf volume for both white and black acha bread. The optimum recipe consisted 8.0 % acha starch, 2.0 % xanthan gum, 2.0 % CMC and 1.0 % yeast. The majority of the consumer panellists found the crust colour, taste and aroma to be moderately desirable. This implies that most consumers find acha bread to have the potential to be marketed as wheat free bread. The different processing methods baking, boiling, microwaving and steaming, affected the black and white acha starch hydrolysis. The amount of starch hydrolysed for the different processing methods was in the following order: baking > boiling > microwaving > steaming. It can thus be concluded that different processing methods affects the micro structure and physical properties of the acha and wheat samples which thus influence their starch hydrolysis. The equilibrium percentage of starch hydrolysed after 180 min incubation was affected differently for the various starches, black acha, white acha and wheat starch by the different processing methods and times. In the case of baking black acha starch and wheat bread were affected similarly. However, this was not the case for microwaving, steaming and boiling, where both acha starch varieties and wheat starch were affected in the same way. The rate of starch hydrolysis for both acha varieties and wheat grain for the different processing methods, steaming, boiling, microwaving and baking was affected to the same degree respectively.

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12

Brigden, C. J. "Surface carbohydrates of Serratia marcescens." Thesis, University of Hull, 1985. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.375628.

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13

Kaloo, Sara. "Glycosylation of Carbohydrates by Glycosyltranferases." Thesis, University of Manchester, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.508556.

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14

Straub, Julie Ann. "The total synthesis of carbohydrates." Thesis, Massachusetts Institute of Technology, 1987. http://hdl.handle.net/1721.1/14622.

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15

Fontenelle, Clement. "The synthesis of polyfluorinated carbohydrates." Thesis, University of Southampton, 2015. https://eprints.soton.ac.uk/374676/.

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Carbohydrates are essential to many fundamental biological processes throughout Nature. Although generally specific for their cognate protein receptors, typical protein carbohydrate affinities are only in the micromolar to millimolar range. Polyfluorination has emerged as an attractive strategy to enhance this affinity in order to develop carbohydrate based inhibitors and therapeutics. This thesis describes three syntheses of 3,4-dideoxy 3,3,4,4-tetrafluoro-Dmannopyranose and D-glucopyranose. Polyfluorination of carbohydrates has important consequences on the hydrogen bond properties of the adjacent alcohols and particularly, difluorination in the β-position of an alcohol group is expected to significantly reduce its hydrogen bond acceptor capacity. For these cases, the substitution of the alcohol group for the intrinsically more nucleophilic amino group is proposed in order to restore this hydrogen bond accepting capacity. Hence, the synthesis of 2-amino-2,3,4-trideoxy-3,3,4,4 tetrafluoro-D-mannopyranose, D-glucopyranose, 4- amino-2,3,4-trideoxy-2,2,3,3-tetrafluoro D-galactopyranose and D-glucopyranose as well as 3- amino-2,3-dideoxy-2,2-difluoro-D galactopyranose is reported in this thesis. In the course of this work, a novel diastereoselective Honda-Reformatsky addition reaction of ethyl bromodifluoroacetate to various α-chiral α-oxygenated N-tert-butanesulfinylimines is described to access to α,α difluoro-β-amino acids and 2,2-difluoro-3-amino carbohydrate analogues. In addition, an extension of the Konno procedure to introduce a tetrafluoroalkylidene moiety was developed.

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16

Ismail, Dayana Qhairunisa. "Off-template functionalisation of carbohydrates." Thesis, University of Manchester, 2012. https://www.research.manchester.ac.uk/portal/en/theses/offtemplate-functionalisation-of-carbohydrates(d052ed49-e722-4af4-a8d4-348b153adbd2).html.

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The conjugate addition of organometallic reagents to α,β-unsaturated carbonyl compounds has been studied extensively and is now one of the most important methods for carbon-carbon bond formation. In devising a novel approach to the synthesis of C-glycosides such as gilvocarcin M, we had occasion to investigate the conjugate addition reactions of a diverse range of nucleophilic reagents (i.e. cuprate, RMgX, R-Li, NR2 and ylides) with a number of γ-alkoxy-α,β-unsaturated compounds (esters, ketones, aldehydes, nitro and sulfones): a sequence which hitherto has received scant attention. The stereochemical outcome of these conjugate addition reactions has been elucidated and the stereochemical rationale for the observed sense of asymmetric induction is also discussed.

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17

Blixt, Ola. "Enzymatic solid-phase synthesis of carbohydrates /." Uppsala : Swedish Univ. of Agricultural Sciences (Sveriges lantbruksuniv.), 1999. http://epsilon.slu.se/avh/1999/91-576-5704-1.pdf.

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18

Lunn, R. J. "Enantiospecific syntheses of alkaloids from carbohydrates." Thesis, University of Oxford, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.376938.

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19

Smith, Kirsten Elisabeth. "Carbohydrates, insulin and the cardiovascular system." Thesis, University of Nottingham, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.546513.

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20

Burroughs, Laurence. "Investigating the prebiotic genesis of carbohydrates." Thesis, University of York, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.546821.

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21

Shan, Yulong. "Bioactive carbohydrates : isolation, synthesis and conjugation." Thesis, Bangor University, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.556079.

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In this thesis four projects related to bioactive carbohydrates are described. The first project is about the extraction of iminosugars from Hyacinthoides non-scripta. This is the first time that extraction from English bluebell seeds has been described. Efficient extraction and isolation methods are reported. Another project discusses the development of a total synthetic carbohydrate conjugate vaccine candidate against Streptococcus pneumoniae type 14 using Gold nanoparticles as carrier. The synthetic pathway of the introduction of a linker for conjugation, and the deprotection of the tetrasaccharide corresponding to the repeating unit of the Streptococcus pneumoniae type 14 capsular polysaccharide is described. The biological results of the developed vaccine candidate are briefly discussed. In the third project, attempts to synthesise regioselectively sulfated disaccharides to be used in binding studies with FedF adhesin of E. coli are described. In this section, an improved high-yielding method based on the Heyns rearrangement for the synthesis of N-acetyl lactosamine (LacNAc) is also reported. In the fourth part, conjugation of the Lewis b hexasaccharide to be used for studies of Lewis b blood group antigen binding adhesin is reported.

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22

Zhu, Fan, and 朱帆. "Interactions of carbohydrates with phenolic compounds." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2010. http://hub.hku.hk/bib/B45584710.

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23

Daly, Mark Elliot. "The metabolic effects of dietary carbohydrates." Thesis, University of Newcastle Upon Tyne, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.341781.

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24

Rullay, Atvinder Kumar. "Investigations of chemoenzymatic synthesis of carbohydrates." Thesis, University of Warwick, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.342690.

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25

Tang, Min. "Novel biodegradable polyesters derived from carbohydrates." Thesis, Imperial College London, 2009. http://hdl.handle.net/10044/1/9017.

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This thesis concerns the synthesis of new biodegradable polyesters from carbohydrates.All the new products have been characterised using nuclear magnetic resonance (NMR)spectroscopy and mass spectrometry; some have been studied using X-raycrystallography. In Chapter 1, which is the introduction, some of the leadingbiodegradable polymers are introduced, in particular attention is paid to polyesterswhich are synthesised from carbohydrates. In addition, the standard polymerisationmethods for the polyester synthesis - ring opening polymerisation and steppolymerisation - are described. Chapter 2 details the synthesis and polymerisation ofacetic acid 5-acetoxy-6-oxo-tetrahydro-pyran-2-yl methyl ester. Three differentinitiating systems have been used for ring opening polymerisations; the kinetics and thepolymer product of the polymerisation are discussed. L-Lactide was used incopolymerisations with acetic acid 5-acetoxy-6-oxo-tetrahydro-pyran-2-yl methyl ester;the copolymers show distinct thermal properties and accelerated degradation ratescompared with poly(L-Lactide) (PLLA). Chapter 3 involves applying functionalisedcarbohydrates, with one free hydroxyl group, as the co-initiator for the ring openingpolymerisation (ROP) of L-lactide. The polymerisations were well controlled with linearrelationships between the percentage lactide conversion and the polymer?s molecularweight. The carbohydrates form the functionalised end group of the PLLA, which, inturn, improve the hydrophilicity of the resulting PLLA. These end-group functionalisedpolylactides have been used as the matrix for human-osteoblast-derived osteosarcomacells (SaOS-2 cells) culturing, and these studies proved that the carbohydrate endgroups were non toxic. Chapter 4 describes the synthesis of a series of othercarbohydrate lactones derived from D-glucono-1,5-lactone, D-xylose and 2-deoxy-Dribose;the lactones include 2,3,4-tri-O-benzyl-D-xylonolactone, 6-methyl-2-oxotetrahydro-2H-pyran-3-yl acetate, (S)-6-(benzyloxymethyl)-tetrahydropyran-2-one. TheROP of these lactones resulted in formation of low molecular weight oligomers, exceptfor 2,3,4-tri-O-benzyl-D-xylonolactone, which can not be polymerised. Chapter 5describes the overall conclusions resulting from the experiments described in the thesis.Chapter 6 is the experimental section and thus provides a detailed description of thesynthesis of all the compounds prepared in the thesis and their analytical data. TheAppendices include two papers that have already been published, describing some ofthe work in the thesis; important additional NMR spectra and MALDI-ToF spectra; andthe complete X-ray crystallography data.

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26

Licisyn, Thomas A. "Synthesis of cyclopropyl glycosides and glycosyl phenylsulfinate esters applications in carbohydrate chemistry /." Click here for download, 2007. http://proquest.umi.com/pqdweb?did=1276418261&sid=2&Fmt=2&clientId=3260&RQT=309&VName=PQD.

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27

Zhang, Zhiyuan. "Synthesis of the monodeoxy neoglycolipid analogues of globotrioside development of some new methods in carbohydrate chemistry /." Lund : Organic Chemistry 2, Lund Institute of Technology, University of Lund, 1996. http://catalog.hathitrust.org/api/volumes/oclc/39264277.html.

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28

Tonelli, Devin L. "Small Molecule Ice Recrystallization Inhibitors and Their Use in Methane Clathrate Inhibition." Thèse, Université d'Ottawa / University of Ottawa, 2013. http://hdl.handle.net/10393/23994.

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Анотація:

Inhibiting the formation of ice is an essential process commercially, industrially, and medically. Compounds that work to stop the formation of ice have historically possessed drawbacks such as toxicity or prohibitively high active concentrations. One class of molecules, ice recrystallization inhibitors, work to reduce the damage caused by the combination of small ice crystals into larger ones. Recent advances made by the Ben lab have identified small molecule carbohydrate analogues that are highly active in the field of ice recrystallization and have potential in the cryopreservation of living tissue. A similar class of molecules, kinetic hydrate inhibitors, work to prevent the formation of another type of ice – gas hydrate. Gas hydrates are formed by the encapsulation of a molecule of a hydrocarbon inside a growing ice crystal. These compounds become problematic in high pressure and low temperature areas where methane is present - such as an oil pipeline. A recent study has highlighted the effects of antifreeze glycoprotein, a biological ice recrystallization inhibitor, in the inhibition of methane clathrates. Connecting these two fields through the synthesis and testing of small molecule ice recrystallization inhibitors in the inhibition of methane hydrates is unprecedented and may lead to a novel class of compounds.

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29

Lloyd, Pamela G. "Organization of carbohydrate metabolism in vascular smooth muscle." free to MU campus, to others for purchase, 2000. http://wwwlib.umi.com/cr/mo/fullcit?p9974656.

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30

Mendlik, Matthew T. "Syntheses and investigations of 2,6-dideoxysugars contained in diverse bioactive compounds." Connect to resource, 2005. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=osu1120673161.

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Thesis (Ph. D.)--Ohio State University, 2005.
Title from second page of PDF file. Document formatted into pages; contains xix, 347 p.; also includes graphics. Includes bibliographical references (p. 183-192). Available online via OhioLINK's ETD Center

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31

Watt, Matthew J., and mikewood@deakin edu au. "Adrenergic regulation of carbohydrate metabolism during exercise." Deakin University. School of Health Sciences, 2001. http://tux.lib.deakin.edu.au./adt-VDU/public/adt-VDU20051202.092251.

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1. This series of studies was undertaken to examine the adrenergic regulation of carbohydrate metabolism during exercise. Recreationally active males were tested during moderate to intense exercise on a stationary cycle ergometer. Venous and arterial plasma obtained from indwelling catheters was analysed for hormonal and metabolite responses, and hepatic glucose production and glucose uptake were measured using the tracer-dilution method with stable isotopes. Muscle samples were obtained by the needle biopsy technique to examine muscle glycogen utilisation and the flux of related muscle metabolites using enzymatic, fluorometric and radioisotopic techniques. 2. During moderate exercise adrenaline infusion induced a marked hyperglycemia and this was due to reduced glucose uptake rather than enhanced hepatic glucose production. The reduction in glucose uptake was most likely mediated by a decrease in glucose phosphorylation, as indicated by the accumulation of glucose 6-phosphate with adrenaline infusion. 3. The hyperglycemic response to intense exercise was prevented by the administration of α- and β-adrenergic antagonists. Adrenergic blockade was without effect on hepatic glucose production whereas glucose uptake was enhanced when compared with control subjects. These data support the notion that adrenergic mechanisms are more important in restraining glucose uptake than enhancing hepatic glucose production during intense exercise. Other glucoregulatory factors are responsible for the increase in glucose production during intense exercise. 4. Elevated plasma adrenaline levels during moderate exercise in untrained men increases skeletal muscle glycogen breakdown and PDH activation which results

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32

Hudgeons, Jeremy L. "The establishment, biological success and host impact of Diorhabda elongata, imported biological control agents of invasive Tamarix in the United States." Thesis, [College Station, Tex. : Texas A&M University, 2007. http://hdl.handle.net/1969.1/ETD-TAMU-1502.

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33

Säwén, Elin. "NMR spectroscopy and MD simulations of carbohydrates." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2011. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-61569.

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Knowledge about the structure, conformation and dynamics of carbohydrates is important in our understanding of the way carbohydrates function in biological systems, for example in intermolecular signaling and recognition. This thesis is a summary of five papers studying these properties in carbohydrate-containing molecules with NMR spectroscopy and molecular dynamics simulations. In paper I, the ring-conformations of the six-membered rings of two carbaiduronic analogs were investigated. These carbasugars could potentially be used as hydrolytically stable mimics of iduronic acid in drugs. The study showed that the equilibrium is entirely shifted towards the 4C1 conformation. Paper II is an investigation of the conformational flexibility and dynamics of two (1→6)-linked disaccharides related to an oligosaccharide epitope expressed on malignant tumor cells. In paper III, the conformational space of the glycosidic linkage of an alfa-(1→2) linked mannose disaccharide present in N- and O-linked glycoproteins, was studied. A maximum entropy analysis using different priors as background information was used and four new Karplus equations for 3JC,C and 3JC,H coupling constants, related to the glycosidic linkage, were presented. Paper IV describes a structural elucidation of the exopolysaccharide (EPS) produced by Streptococcus thermophilus ST1, a major dairy starter used in yoghurt and cheese production. The EPS contains a hexasaccharide repeating unit of d-galactose and d-glucose residues, which is a new EPS structure of the S. thermophilus species. In paper V, the dynamics of three generations of glycodendrimers were investigated by NMR diffusion and 13C NMR relaxation studies. Three different correlations times were identified, one global correlation time describing the rotation of the dendrimer as a whole, one local correlation time describing the reorientation of the C-H vectors, and one correlation time describing the pulsation of a dendrimer branch.

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34

DiCesare, John C. "Carbohydrates as chiral auxiliaries in organometallic reactions." Diss., Georgia Institute of Technology, 1992. http://hdl.handle.net/1853/27389.

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35

Stimpson, William Thomas. "The asymmetric synthesis of isotopically labelled carbohydrates." Thesis, University of Manchester, 2008. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.488773.

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36

Moore, Sarah G. "The synthesis of phosphonate analogues of carbohydrates." Thesis, University of Manchester, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.527569.

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This t~esis is concerned with the synthesis of phosphonate analogues of carbohydrates as stable lsosteres of the corresponding phosphates. Analogues of glucose-6-phosphate (Part A) and mannose-6-phosphate (Part B) were prepared. Part A Glucose-6-phosphatase plays a central role in the homeostatic regulation of blood glucose, by catalysing the conversion of glucose-6-phosphate to glucose in the terminal steps of both gluconeogenesis and glycogenolysis. Abnormally high glucose-6- phosphatase activity has been noted in some cases of diabetes mellitus. Phosphonate analogues of glucose-6-phosphate (which contain a P-C linkage in place of the P-O-C moiety of the corresponding phosphate) are potential inhibitors of glucose-6-phosphatase and therefore could have an application in the treatment of diabetes. Here, the syntheses of three phosphonate analogues of glucose-6-phosphate are described. A non-isosteric phosphonate analogue (in which the phosphate bridging oxygen of glucose-6-phosphate has been removed) was prepared in seven steps from D-glucose, the key step being an Arbuzov reaction between triethyl phosphite and a benzyl protected glucose-6-bromide. Isosteric and isoelectronic phosphonate analogues (in which the bridging oxygen of glucose-6-phosphate has been replaced by a methylene [CH2] and a difluoromethylene [CF2] group, respectively) were also synthesised in seven steps from D-glucose, the key step being the nucleophilic attack of anion (EtO)2P(O)CX2- (X = H, F) on the C-6 triflate of a benzyl protected glucose derivative. PartB Transforming growth factor-~l (TGF-~l) is one of several cytokines implicated in scarring during adult wound healing. TGF-~l is stored in an inert form and activation is due, in part, to the binding of mannose-6-phosphate residues on latent TGF-~l to the mannose-6-phosphate/insulin-like growth factor-II (M-6-PIIGF-II) receptor. Phosphonate analogues of mannose-6-phosphate could inhibit TGF-~l activation by competitive inhibition of binding of latent TGF-~l to the M-6-PIIGF-II receptor and therefore have antiscarring potential. A non-isosteric phosphonate analogue of mannose-6-phosphate was prepared in eight steps from D-mannose utilising Arbuzov chemistry. Initial evaluation in a rat model indicated an anti-scarring effect. An a-hydroxy phosphonate analogue of mannose-6-phosphate was prepared utilising a Pudovic reaction between the anion of dibenzyl phosphite and the C-6 aldehyde of a benzyl protected mannose derivative. The Pudovic reaction proceeded with a diastereoisomeric excess of -80 % and various attempts were made to determine the absolute configuration of the major diastereoisomer. Several esterified derivatives were prepared in an attempt to obtain crystals suitable for X-ray analysis, however only oils or fine powders were formed. Reactions designed to synthesise conformationally restricted analogues in order to determine the conformation by NOE NMR spectroscopy are also described, however these were not successful. Phosphorylated a-I,2-linked mannobiosides are known to bind strongly to the M- 6-P/IGF-II receptor, and therefore an a-I,2-linked mannose disaccharide with a nonisosteric phosphonate at the non-reducing terminus was prepared. The coupling of a thioglycoside donor bearing a 6-phosphonate with the 1,3,4,6-tetra-O-acetyl-~-Dmannopyranoside acceptor was achieved with the use of the mild activator, Niodosuccinimide. Finally, methodology towards the synthesis of a bidentate ligand incorporating two mannose-6-phosphate groups, together with. the a-I ,2-mannosi~ic linkage is described. A cyclohexane-I,2-diacetal protected a-I ,2-hnked mannose dlsacchande _ beanng a 6- phosphonate moiety at the non-reducing terminus was prepared from protected monosaccharides, again using a mild activation procedure.

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37

Yin, Xiang Sheng. "Physical and enzymic modification of barley carbohydrates." Thesis, Heriot-Watt University, 1986. http://hdl.handle.net/10399/1966.

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38

Aloui, Mahmoud. "Use of carbohydrates in pseudo-sugar synthesis." Thesis, University of Salford, 1992. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.334027.

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39

Patel, Mitul Kiran. "Unravelling the biological roles of charged carbohydrates." Thesis, University of Oxford, 2011. http://ora.ox.ac.uk/objects/uuid:6fb4de15-5585-4f62-ae56-4c6bf32593ab.

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The phosphate and sulfate esters of carbohydrates are widespread in nature, where they partake in a variety of signalling roles. This thesis focuses on the involvement of trehalose-6-phosphate (Tre-6-P) in regulating plant growth, and the function of sulfated carbohydrates in the immune response. In plants, Tre-6-P is a critical messenger that conveys environmental information for the control of metabolic state. Beneficial natural conditions lead to an increase in the in vivo concentration of Tre-6-P, which in turn triggers biosynthetic processes facilitating plant growth. However, the mechanism by which this effect is exerted is largely unknown. A thorough understanding of this fundamental signalling pathway could allow considerable improvements in agriculture. Recent evidence has found an interaction between Tre 6 P and a protein kinase system (SnRK1), mediated via an intermediary protein whose identity is unknown. Our efforts to identify this elusive protein are presented. Methodology is developed to allow the synthesis of Tre-6-P analogues for defining structure-activity relationships, with particular attention focused towards the desymmetrization of trehalose and the control of phosphate migrations. Tre-6-P is tethered to a solid phase resin allowing affinity extraction of putative intermediary factors. The 14-3-3 class of regulatory proteins is identified as a potential binding partner of Tre-6-P. The mannose receptor (MR) is an essential element of the mammalian immune system. Expressed on macrophages, the protein can bind and internalize pathogens through their surface exposed carbohydrates. However, the receptor can also dimerize, upon which it is able to divalently bind to sulfated carbohydrates. The biological significance of this sulfate binding is poorly understood. Current hypotheses invoke a role for the sulfate mediated trafficking of MR dimers to areas of B-cell maturation for antigen presentation, thus linking the innate and adaptive defence mechanisms. In any case, the dimerization of the MR is an essential prerequisite for interaction with carbohydrate sulfates. Methodology is required to probe this dimerization on the surface of cells under their native conditions. In this thesis, we use fluorescence microscopy to study the binding of various probes to macrophage and endothelial liver derived cell lines. Results of our initial investigations are presented that show internalization of the probes. The use of FRET imaging to directly probe the presence of MR dimers is studied.

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40

Lewallen, Daniel M. "Development of synthetic carbohydrates for capturing toxins." University of Cincinnati / OhioLINK, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1288969515.

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41

GoncÌ§alves, Pedro Miguel Lopes. "Modification of carbohydrates using enzymes as catalysts." Thesis, University of Liverpool, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.288199.

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42

Poland, Lynette C. "The effect of a carbohydrate supplement on multiple bout resistance performance training during energy restriction in male resistance trainers." Thesis, This resource online, 1994. http://scholar.lib.vt.edu/theses/available/etd-06162009-063322/.

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43

Dhake, Parag. "Reexamination of Reverse Anomeric Effect (RAE)." Fogler Library, University of Maine, 2008. http://www.library.umaine.edu/theses/pdf/DhakeP2008.pdf.

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44

Ladomenou, Kalliopi. "Podand-type receptors for sugar recognition." Thesis, University of Liverpool, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.250367.

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45

Manning, Charles Edward. "Formation and melting of gellan polysaccharide gels." Thesis, Cranfield University, 1992. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.282399.

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46

Houtkooper, Linda, and Jaclyn Maurer. "Carbohydrate Needs." College of Agriculture and Life Sciences, University of Arizona (Tucson, AZ), 2006. http://hdl.handle.net/10150/146628.

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47

Sundin, Birgitta. "Dental caries and sugar-containing products analytical studies in teenagers /." Malmö [Sweden] : Dept. of Pedodontics, Faculty of Odontology, Lund University, 1994. http://catalog.hathitrust.org/api/volumes/oclc/32290695.html.

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48

Lim, Tang Kuan. "NMR studies of carbohydrates in the solid state." Thesis, University of British Columbia, 1985. http://hdl.handle.net/2429/27129.

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The work described herein entails the application of solid-state n.m.r. methods to both mono- and polysaccharide carbohydrates. Two major n.m.r. methods have been evaluated for studying these substances, namely, the carbon-13 cross-polarization-magic angle spinning method and the deuterium quadrupole echo method. Heptakis-(2,6-di-O-methyl)- β-cyclodextrin and β-cyclodextrin peracetate were prepared and, together with α-and β-cyclodextrins as hosts, were used to encage a variety of organic guest molecules. A number of metal sugar conjugates were prepared according to the procedures documented in this laboratory. Firstly, chelate coordination complexes were synthesized by forming salicylaldimine ligands derived from combinations of amino sugars (methyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside or 1 , 3 , 4 , 6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose) and salicylaldehyde, with subsequent complexation of these to copper(II), zinc(ll), and cobalt(Il) ions. Similarly, chitosan Schiff's bases were prepared and complexed to copper(II) ion. Application of the ¹³C-cross-polarization-magic angle spinning method in the spectral assignment of cyclodextrin inclusion complexes and metal sugar conjugates in the solid state has been demonstrated. In all cases, recourse to solution spectra was necessary for correct assignments of individual carbon resonances. The sugar resonances of cyclodextrins are relatively broad and are complicated by the substantial splittings. The rationales for such observations were drawn from comparative studies, based on closely related guest molecules. The smaller guest molecules were least affected by the cavity size of the host molecule heptakis-( 2 , 6-di-O-methyl) -β-cyclodextr in and the isotropic chemical shift values were similar to those measured for solutions. These values suggest that the guest molecules undergo anisotropic motion, which can be detected by the use of the dipolar dephasing technique. Studies of metal sugar conjugates by ¹³C n.m.r. revealed that paramagnetic ions have profound effects on the resolution obtained. The high concentrations of these ions result in broad featureless spectra. On the other hand, the diamagnetic ions proved to have little effect on the isotropic chemical shifts of the sugar chelates. The deuterium quadrupole echo method has been used specifically to study the mobility of the guest molecules encaged in cyclodextrins. The "powder-type" spectra obtained were then compared with results reported in the literature in order to define the types of molecular motion.
Science, Faculty of
Chemistry, Department of
Graduate

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49

Vanmaele, Rosa Pauline. "Role of carbohydrates in enteropathogenic Escherichia coli adherence." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1999. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape7/PQDD_0003/NQ39602.pdf.

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50

Eklund, Robert. "Computational Analysis of Carbohydrates : Dynamical Properties and Interactions." Doctoral thesis, Stockholm : Department of Organic Chemistry, Stockholm University, 2005. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-538.

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