Relevant bibliographies by topics / Microsclerodermin

Academic literature on the topic 'Microsclerodermin'

Author: Grafiati
Published: 4 June 2021
Last updated: 20 February 2023

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Journal articles on the topic "Microsclerodermin"

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Zhu, Jidong, and Dawei Ma. "Total Synthesis of Microsclerodermin E." Angewandte Chemie 115, no. 43 (November 10, 2003): 5506–9. http://dx.doi.org/10.1002/ange.200352423.

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Zhu, Jidong, and Dawei Ma. "Total Synthesis of Microsclerodermin E." Angewandte Chemie International Edition 42, no. 43 (November 10, 2003): 5348–51. http://dx.doi.org/10.1002/anie.200352423.

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Melikhova, Ekaterina Y., Robert D. C. Pullin, Christian Winter, and Timothy J. Donohoe. "Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision." Angewandte Chemie International Edition 55, no. 33 (July 15, 2016): 9753–57. http://dx.doi.org/10.1002/anie.201604764.

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Melikhova, Ekaterina Y., Robert D. C. Pullin, Christian Winter, and Timothy J. Donohoe. "Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision." Angewandte Chemie 128, no. 33 (July 15, 2016): 9905–9. http://dx.doi.org/10.1002/ange.201604764.

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Winter, Christian, Robert D. C. Pullin, and Timothy J. Donohoe. "Diastereoselective synthesis of the 5-hydroxy-pyrrolidinone amino acid of the microsclerodermins and model studies for an end-game strategy for microsclerodermin B." Tetrahedron Letters 58, no. 7 (February 2017): 602–5. http://dx.doi.org/10.1016/j.tetlet.2016.12.045.

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Bewley, Carole A., Cecile Debitus, and D. John Faulkner. "Microsclerodermins A and B. Antifungal Cyclic Peptides from the Lithistid Sponge Microscleroderma sp." Journal of the American Chemical Society 116, no. 17 (August 1994): 7631–36. http://dx.doi.org/10.1021/ja00096a020.

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Shuter, Emily C., Hung Duong, Craig A. Hutton, and Malcolm D. McLeod. "The enantioselective synthesis of APTO and AETD: polyhydroxylated β-amino acid constituents of the microsclerodermin cyclic peptides." Organic & Biomolecular Chemistry 5, no. 19 (2007): 3183. http://dx.doi.org/10.1039/b707891a.

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Qureshi, Asfia, Patrick L. Colin, and D. John Faulkner. "Microsclerodermins F–I, Antitumor and Antifungal Cyclic Peptides from the Lithistid Sponge Microscleroderma sp." Tetrahedron 56, no. 23 (June 2000): 3679–85. http://dx.doi.org/10.1016/s0040-4020(00)00286-6.

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BEWLEY, C. A., C. DEBITUS, and D. J. FAULKNER. "ChemInform Abstract: Microsclerodermins A and B. Anifungal Cyclic Peptides from the Lithistid Sponge Microscleroderma sp." ChemInform 26, no. 15 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199515241.

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Schmidt, Eric W., and D. John Faulkner. "Microsclerodermins C - E, antifungal cyclic peptides from the lithistid marine sponges Theonella sp. and Microscleroderma sp." Tetrahedron 54, no. 13 (March 1998): 3043–56. http://dx.doi.org/10.1016/s0040-4020(98)00054-4.

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Dissertations / Theses on the topic "Microsclerodermin"

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Liu, Yong-Peng. "Total Synthesis of Microsclerodermin D." Thesis, université Paris-Saclay, 2020. http://www.theses.fr/2020UPASF024.

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La microsclerodermine D est un peptide macrocyclique d’origine marine qui comporte six amino acides, dont deux sont disponibles commercialement : la glycine (Gly) et la sarcosine (Sar). Les quatre autres amino acides : l’acide (R)-γ-amino-β-hydroxybutyrique (GABOB), le D-6-chlorotryptophane (6-Cl-Trp), un β-amino acide polyhydroxylé (APTO) et l’acide 3-amino-4-hydroxypyrrolidinoacetique (PyrrAA) seront préparés via de nouvelles voies de synthèse. Notre objectif est de développer une voie de synthèse de la microsclerodermine D modulable et qui permettrait la synthèse d’autres membres de la famille des microsclerodermines et d’analogues. Nos nous intéresserons également à de potentielles études permettant d’évaluer leurs propriétés biologiques et leur potentiel en tant qu’agent anticancéreux
Microsclerodermin D is a macrocyclic peptide of marine origin which contains six amino acids, of which two are commercially available: glycine (Gly) and sarcosine (Sar). The four other amino acids: (R)-γ-amino-β-hydroxybutyric acid (GABOB), D-6-chlorotryptophan (6-Cl-Trp), a polyhydroxylated β-amino acid (APTO) and 3-amino-4-hydroxypyrrolidinoacetic acid (PyrrAA) will be accessible by new synthetic routes. Our goal is to develop a modular synthetic route to microsclerodermin D that could be applicable for the preparation of other microsclerodermin family members and analogues thereof. We are also looking forward to make some investigations on their biological activities or potential as anticancer drug
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Kershaw, Jessica A. "Studies towards the synthesis of microsclerodermin F." Thesis, University of Oxford, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.540282.

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Shuter, Emily Clare. "Studies toward the synthesis of the microsclerodermin natural products." Faculty of Science, School of Chemistry, University of Sydney, 2006. http://hdl.handle.net/2123/1970.

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Doctor of Philosophy (PhD), Science
A concise stereo-selective synthesis of a protected form of APTO 1, an unusual amino acid component of microsclerodermin C 2, was undertaken. Sequential Sharpless Asymmetric Aminohydroxylation (AA) and Asymmetric Dihydroxylation (AD) reactions were used to introduce the chiral amino and hydroxyl groups. Specific directing groups were chosen to ensure high regio- and enantio-selectivity in these reactions. The target compound was reached in a linear reaction sequence of fourteen steps. The strategy was designed to generate common intermediates which could be used to access analogous amino acid fragments in other microsclerodermins. A protected form of AETD 3, from microsclerodermin E, was synthesised via a late-stage common intermediate. Initial studies into the modification of the sequence to allow access to AMPTD 4 and 10-methyl AMPTD 5 were made.
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Shuter, Emily Clare. "Studies toward the synthesis of the microsclerodermin natural products." Connect to full text, 2005. http://ses.library.usyd.edu.au/handle/2123/1970.

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Thesis (Ph. D.)--University of Sydney, 2006.
Title from title screen (viewed April 1, 2008). Submitted in partial fulfilment of the requirements for the degree of Doctor of Philosophy to the School of Chemistry, Faculty of Science. Degree awarded 2006; thesis submitted 2005. Includes bibliographical references. Also available in print form.
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Melikhova, Ekaterina. "Total synthesis and stereochemical reassignment of dehydromicrosclerodermin B and microsclerodermin J." Thesis, University of Oxford, 2016. https://ora.ox.ac.uk/objects/uuid:a0894f3b-0209-4feb-957e-9c4b0bdb60a8.

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This thesis describes research towards the total synthesis of two marine natural products, dehydromicrosclerodermin B and microsclerodermin J. The synthesis of the most complex subunit of these peptides, AMMTD, was accomplished in a longest linear sequence of 21 steps starting from (S)-Roche ester. Preliminary results conducted by other group members were improved; the key cuprate displacement reaction and the final steps of the synthetic sequence were developed. Subsequently, AMMTD-GABOB dipeptide was synthesised and coupled with the northern hemisphere. An appropriate protecting group strategy was developed such that macrolactamisation and subsequent protecting group removal could be achieved. This required the design of a new approach to the synthesis of the tryptophan-2-carboxylic acid. An "end-game" strategy, which had previously been developed on model substrates, failed on late-stage cyclic or linear hexapeptides. Because of this, studies turned to the completion of a synthesis of dehydromicrosclerodermin B. Comparison of the data for synthetic and natural dehydromicrosclerodermin B revealed a mistake in the assignment of the (45S)-configuration. The corresponding (45R)-epimer was synthesised and its data were in a good agreement with those of dehydromicrosclerodermin B. Based on the reassignment of the C45 stereocentre of dehydromicrosclerodermin B, the total synthesis of microsclerodermin J containing a reassigned (R)-configured pyrrolidinone unit was accomplished. NMR data for synthetic and natural microsclerodermin J were in complete agreement, confirming that the initial stereochemical assignment of this natural product was incorrect.
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Foster, Emma Marie. "Asymmetric synthesis of amino polyols." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:3393ed50-d465-491b-9270-c5f5228572ec.

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This thesis is concerned with the development of methodology for the asymmetric synthesis of a range of amino polyol containing compounds. Chapter 1 highlights the abundance of the amino polyol motif in nature, the wide range of biological activities displayed by amino polyol containing compounds, and their occurrence in drug molecules. A variety of different methods for the synthesis of stereodefined amino polyols is then discussed. Chapter 2 details a full investigation into the doubly diastereoselective conjugate addition reactions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to enantiopurealpha,beta-unsaturated esters which contain a dioxolane unit. The “matched” conjugate addition reactions were further coupled with a highly diastereoselective in situ enolate oxidation using camphorsulfonyloxaziridine for the synthesis of keyalpha-hydroxy-beta-amino ester intermediates. Subsequent cyclisation and further elaboration allowed access to a range of amino polyol containing compounds including imino sugars, amino sugars, and amino acids. Chapter 3 extends the investigation into the doubly diastereoselective lithium amide conjugate addition reaction to enantiopure alpha,beta-unsaturated esters which contain two dioxolane units. A full assessment into the conjugate addition of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a series of D-pentose derived alpha,beta-unsaturated esters is reported. Subsequent elaboration of thebeta-amino ester products of these conjugate addition reactions resulted in the synthesis of (2'S,3'S,4'R)-dihydroxyhomoproline and (2'S,3'R,4'S)-dihydroxyhomoproline. Chapter 4 describes the asymmetric syntheses of protected forms of APTO and AETD, the 2,4,5-trihydroxy substitutedbeta-amino acid residues found within the hexapeptide marine natural products microsclerodermins C, D and E. The optimised synthetic routes to APTO and AETD involved three key steps: a diastereoselective aminohydroxylation [via conjugate addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide to an achiralalpha,beta-unsaturated ester followed by in situ enolate oxidation with camphorsulfonyloxaziridine], a diastereoselective dihydroxylation, and an olefination. Chapter 5 contains full experimental procedures and characterisation data for all compounds synthesised in chapters 2, 3 and 4.
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Rathi, Akshat Hemant. "Studies towards the synthesis of complex amino acids derived from microsclerodermins." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:ca121a22-aee7-4da5-bd0d-dc7ee6e53bea.

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This thesis describes the studies towards the synthesis of β-amino acids found in the microsclerodermins, a family of complex macrocyclic hexapeptides. These β-amino acids have four or five contiguous stereocentres and an aliphatic side-chain. The synthetic route utilised an aminohydroxylation reaction to install the most challenging moiety in the structure - the 1,2- amino alcohol. The work aimed to construct the core structure (five contiguous stereocentres) of the β-amino acids and install the side-chain later to enable the synthesis of multiple members (A, B, F, G, H and I) of the microsclerodermin family. The synthesis started with Roche ester, which contained the first methyl stereocentre. It was converted to the diene precursor in four high yielding steps. The next two stereocentres were installed via a Sharpless asymmetric dihydroxylation. With the appropriate protecting groups in place, the remaining two stereocentres were to be installed via a Sharpless asymmetric aminohydroxylation. Various reported reagents and conditions were used to effect the transformation, but the attempts were unsuccessful. This forced us to alter our synthetic plans, and the revised synthetic route involved the use of the tethered aminohydroxylation (TA) reaction developed by the Donohoe group. After the development of an efficient protocol to prepare the TA-precursor, the alkene, with three stereocentres already in place, was successfully converted to the desired stereopentad via the TA-reaction (10 steps, 11% overall yield). With the stereopentad in hand, installation of the side-chain of the β-amino acids through an alkenyl or alkyl linkage was investigated. For alkenyl-linked side-chains, the appropriate aldehyde was synthesised, but attempts to effect the transformation via a Horner-Wadsworth- Emmons reaction or a Witting reaction failed. With lessons learnt from those, we then focused our efforts on installing an alkyl-linked side-chain. In this case, we were able to install a side- chain via a copper-mediated displacement reaction, which gave us a protected form of the precursor of the β-amino acid of microsclerodermin B. Finally, various efforts to study the reactivity of the stereopentad and the investigations into finding the most effective set of protecting groups have been used to propose a synthetic route for the incorporation of the β- amino acid into the macrocycle.
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Book chapters on the topic "Microsclerodermin"

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Burnett, Cameron M., and Robert M. Williams. "Studies towards the total synthesis of microsclerodermin G." In 19th International Congress on Heterocyclic Chemistry, 126. Elsevier, 2003. http://dx.doi.org/10.1016/b978-0-08-044304-1.50118-0.

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You might also be interested in the extended bibliographies on the topic 'Microsclerodermin' for particular source types:
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