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Littérature scientifique sur le sujet « Bioconjugation reaction »

Auteur : Grafiati
Publié le 9 mars 2023
Mis à jour le 10 mars 2023

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Articles de revues sur le sujet "Bioconjugation reaction"

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Flood, Dillon T., Jordi C. J. Hintzen, Kyle W. Knouse, David E. Hill, Chenxi Lu, Philip A. Cistrone, Jason S. Chen, Takanori Otomo et Philip E. Dawson. « Selenomethionine as an expressible handle for bioconjugations ». Proceedings of the National Academy of Sciences 118, no 8 (18 février 2021) : e2005164118. http://dx.doi.org/10.1073/pnas.2005164118.

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Site-selective chemical bioconjugation reactions are enabling tools for the chemical biologist. Guided by a careful study of the selenomethionine (SeM) benzylation, we have refined the reaction to meet the requirements of practical protein bioconjugation. SeM is readily introduced through auxotrophic expression and exhibits unique nucleophilic properties that allow it to be selectively modified even in the presence of cysteine. The resulting benzylselenonium adduct is stable at physiological pH, is selectively labile to glutathione, and embodies a broadly tunable cleavage profile. Specifically, a 4-bromomethylphenylacetyl (BrMePAA) linker has been applied for efficient conjugation of complex organic molecules to SeM-containing proteins. This expansion of the bioconjugation toolkit has broad potential in the development of chemically enhanced proteins.
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Tantipanjaporn, Ajcharapan, et Man-Kin Wong. « Development and Recent Advances in Lysine and N-Terminal Bioconjugation for Peptides and Proteins ». Molecules 28, no 3 (21 janvier 2023) : 1083. http://dx.doi.org/10.3390/molecules28031083.

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The demand for creation of protein diversity and regulation of protein function through native protein modification and post-translational modification has ignited the development of selective chemical modification methods for peptides and proteins. Chemical bioconjugation offers selective functionalization providing bioconjugates with desired properties and functions for diverse applications in chemical biology, medicine, and biomaterials. The amino group existing at the lysine residue and N-terminus of peptides and proteins has been extensively studied in bioconjugation because of its good nucleophilicity and high surface exposure. Herein, we review the development of chemical methods for modification of the amino groups on lysine residue and N-terminus featuring excellent selectivity, mild reaction conditions, short reaction time, high conversion, biocompatibility, and preservation of protein integrity. This review is organized based on the chemoselectivity and site-selectivity of the chemical bioconjugation reagents to the amino acid residues aiming to provide guidance for the selection of appropriate bioconjugation methods.
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Choi, Eun Joung, Dongwook Jung, Jong-Seo Kim, Yan Lee et B. Moon Kim. « Chemoselective Tyrosine Bioconjugation through Sulfate Click Reaction ». Chemistry - A European Journal 24, no 43 (18 juillet 2018) : 10948–52. http://dx.doi.org/10.1002/chem.201802380.

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Miyabe, Hideto, Eito Yoshioka, Yuya Goto et Ikko Minato. « Aqueous-Medium Selective Modification of Cysteine and Related Thiols with Tricyclic Oxygen-Heterocycles ». Synthesis 49, no 21 (25 juillet 2017) : 4887–92. http://dx.doi.org/10.1055/s-0036-1588497.

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The utility of tricyclic oxygen-heterocycles as a reagent for the thiol-selective modification toward bioconjugation was demonstrated by the use of l-cysteine, homocysteine, captopril, and glutathione as a nucleophile having a thiol group. These trapping reactions proceeded under the mild and aqueous reaction conditions.
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Draganov, Alexander B., Ke Wang, Jalisa Holmes, Krishna Damera, Danzhu Wang, Chaofeng Dai et Binghe Wang. « Click with a boronic acid handle : a neighboring group-assisted click reaction that allows ready secondary functionalization ». Chemical Communications 51, no 82 (2015) : 15180–83. http://dx.doi.org/10.1039/c5cc05890b.

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Hörner, S., C. Uth, O. Avrutina, H. Frauendorf, M. Wiessler et H. Kolmar. « Combination of inverse electron-demand Diels–Alder reaction with highly efficient oxime ligation expands the toolbox of site-selective peptide conjugations ». Chemical Communications 51, no 55 (2015) : 11130–33. http://dx.doi.org/10.1039/c5cc03434e.

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Song, Chunlan, Kun Liu, Zhongjie Wang, Bo Ding, Shengchun Wang, Yue Weng, Chien-Wei Chiang et Aiwen Lei. « Electrochemical oxidation induced selective tyrosine bioconjugation for the modification of biomolecules ». Chemical Science 10, no 34 (2019) : 7982–87. http://dx.doi.org/10.1039/c9sc02218j.

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Montalvan-Sorrosa, D., J. L. González-Solis, J. Mas-Oliva et R. Castillo. « Filamentous virus decoration with gold nanoparticles : global fingerprints of bionanocomposites acquired with SERS ». RSC Adv. 4, no 100 (2014) : 57329–36. http://dx.doi.org/10.1039/c4ra10656c.

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Ramos-Tomillero, Iván, Gema Pérez-Chacon, Beatriz Somovilla-Crespo, Francisco Sánchez-Madrid, Carmen Cuevas, Juan Manuel Zapata, Juan Manuel Domínguez, Hortensia Rodríguez et Fernando Albericio. « From Ugi Multicomponent Reaction to Linkers for Bioconjugation ». ACS Omega 5, no 13 (23 mars 2020) : 7424–31. http://dx.doi.org/10.1021/acsomega.0c00099.

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Hu, Xianglong, Xueqian Zhao, Benzhao He, Zheng Zhao, Zheng Zheng, Pengfei Zhang, Xiujuan Shi et al. « A Simple Approach to Bioconjugation at Diverse Levels : Metal-Free Click Reactions of Activated Alkynes with Native Groups of Biotargets without Prefunctionalization ». Research 2018 (12 décembre 2018) : 1–12. http://dx.doi.org/10.1155/2018/3152870.

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The efficient bioconjugation of functional groups/molecules to targeted matrix and bio-related species drives the great development of material science and biomedicine, while the dilemma of metal catalysis, uneasy premodification, and limited reaction efficiency in traditional bioconjugation has restricted the booming development to some extent. Here, we provide a strategy for metal-free click bioconjugation at diverse levels based on activated alkynes. As a proof-of-concept, the abundant native groups including amine, thiol, and hydroxyl groups can directly react with activated alkynes without any modification in the absence of metal catalysis. Through this strategy, high-efficient modification and potential functionalization can be achieved for natural polysaccharide, biocompatible polyethylene glycol (PEG), synthetic polymers, cell penetrating peptide, protein, fast whole-cell mapping, and even quick differentiation and staining of Gram-positive bacteria, etc. Therefore, current metal-free click bioconjugation strategy based on activated alkynes is promising for the development of quick fluorescence labeling and functional modification of many targets and can be widely applied towards the fabrication of complex biomaterials and future in vivo labeling and detection.
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Thèses sur le sujet "Bioconjugation reaction"

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Gujral, Chirag Harsharan Singh. « Boronic-diol complexation as click reaction for bioconjugation purposes ». Thesis, University of Manchester, 2011. https://www.research.manchester.ac.uk/portal/en/theses/boronicdiol-complexation-as-click-reaction-for-bioconjugation-purposes(a7072d58-2a4f-4d0f-bcab-6cd709bdac12).html.

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The research presented in this thesis focuses on the study of the reaction between boronic acids and diols and its evaluation as a possible "click" reaction, possibly applicable in bioconjugation and drug delivery. A key feature of this reaction is its reversibility at acidic pH, which could allow the release of a diol-containing drug from a bioconjugate in the acidic environment of late endosome/lysosome, possibly after undergoing receptor mediated endocytosis. Over the last two decades various studies have focused on the study of the conjugation of boronic acids to diols using Alizarin Red S as a fluorescence reporter. In this research we have presented an alternative method based on the batochromic shifts of Alizarin Red S absorbance; this method is particularly advantageous in complex systems with an elevated scattering, such as colloidal dispersions or for binding to complexed active compounds. We have therefore demonstrated that this method allows the determination of equilibrium constants between diols (e.g. catecholamines) and boronic acids. We have also demonstrated that the method allows to follow the kinetics of enzymatic reactions involving catechols; in particular, we have focused on cytochrome P450-mediated reactions such as the conversion of estradiol to 2-hydroxyestradiol using CYP1A2, or the demethylation of 3-methoxytyramine to dopamine using CYP2D6. Once we have established a reliable method for following this reaction on low molecular weight compounds, we have applied it to polymeric bioconjugates. Specifically, we have selected hyaluronic acid (HA) as a biocompatible and biodegradable polymeric backbone and produced derivatives containing boronic acids, catechols and dimethylated catechols (as negative controls). The resulting polymers where characterised via UV-Vis, 1H NMR and SLS, also qualitatively evaluating their cytotoxicity and enzymatic degradability. The conjugates with boronic acids showed the lowest cytotoxicity, and the highest degradability. The complexation of HA-boronic derivatives was then studied; using the same library of diols previously used with low molecular weight compounds, evaluating the effect of the presence of the polysaccharidic macromolecular chain.
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Wang, Shujiang. « Insights into dynamic covalent chemistry for bioconjugation applications ». Doctoral thesis, Uppsala universitet, Polymerkemi, 2017. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-329022.

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Dynamic covalent chemistry (DCC) is currently exploited in several areas of biomedical applications such as in drug discovery, sensing, molecular separation, catalysis etc. Hydrazone and oxime chemistry have several advantages, such as mild reaction conditions, selectivity, efficiency, and biocompatibility and therefore, have the potential to be for bioconjugation applications. However, these reactions suffer from major drawbacks of slow reaction rate and poor bond stability under physiological conditions. In this regard, the work presented in this thesis focuses on designing novel bioconjugation reactions amenable under physiological conditions with tunable reaction kinetics and conjugation stability. The first part of the thesis presents different strategies of dynamic covalent reactions utilized for biomedical applications. In the next part, a detailed study related to the mechanism and catalysis of oxime chemistry was investigated in the presence of various catalysts. Aniline, carboxylate and saline were selective as target catalysts and their reaction kinetics were compared under physiological conditions (Paper I and II). Then we attempted to explore the potential of those chemistries in fabricating 3D hydrogel scaffolds for regenerative medicine application. A novel mild and regioselective method was devised to introduce an aldehyde moiety onto glycosaminoglycans structure. This involved the introduction of amino glycerol to glycosaminoglycans, followed by regioselective oxidation of tailed flexible diol without affecting the C2-C3 diol groups on the disaccharide repeating unit. The oxidation rate of the tailed flexible diol was 4-times faster than that of C2-C3 diol groups of native glycosaminoglycan. This strategy preserves the structural integrity of the glycosaminoglycans and provides a functional aldehyde moiety (Paper III). Further, different types of hydrazones were designed and their hydrolytic stability under acidic condition was carefully evaluated. The hydrazone linkage with the highest hydrolytic stability was utilized in the preparation of extracellular matrix hydrogel for delivery of bone morphogenetic proteins 2 in bone regeneration (Paper IV) and studied for controlled release of the growth factor (Paper III). In summary, this thesis presents a selection of strategies for designing bioconjugation chemistries that possess tunable stability and reaction kinetics under physiological conditions. These chemistries are powerful tools for conjugation of biomolecules for the biomedical applications.
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Tona, Rolf. « Bioconjugation and cross-linkage of diene-modified oligodeoxyribonucleotides via the Diels-Alder reaction / ». [S.l.] : [s.n.], 2004. http://www.zb.unibe.ch/download/eldiss/04tona_r.pdf.

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COGHI, MARIA DONATA. « Samdi mass spectrometry for high yield protein modification reaction development ». Doctoral thesis, Università degli Studi di Milano-Bicocca, 2014. http://hdl.handle.net/10281/50887.

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Efficient chemical strategies that attach synthetic molecules to desired positions on protein surfaces are useful tools in the field of chemical biology and represent one major prerequisite for the development of new drugs and materials. Protein modification with polyethylene glycol (PEG) groups is indeed routinely performed on therapeutic proteins to improve serum half-life, or even cytotoxins or imaging agents are efficiently conjugated to cancer-targeting elements. In a typical approach, a synthetic functional group of interest is attached to a uniquely reactive amino acid group introduced by recombinant methods. Most bioconjugation reactions, however, do not reach full conversion. Therefore the development of a straightforward and reliable method to increase the extent of conversion into bioconjugates would be very helpful. In this perspective, we developed a generalizable combinatorial peptide library screening platform suitable for the identification of sequences displaying high levels of reactivity toward a desired bioconjugation reaction. This was achieved by using SAMDI MS technique (Self-Assembled Monolayer and Desorption/Ionization Mass Spectrometry) as a new, efficient and simple method for the evaluation of highly reactive amino acid motifs. The bioconjugation reaction we selected is the oxidative modification of electron-rich tyrosine residues performed using cerium(IV) ammonium nitrate (CAN) as oxidant reagent. The peptides were identified on a 361-member hexapeptide array, wherein the two N- and C-terminal residues to the target residue were varied. The arrays were prepared by immobilizing the peptides to a self-assembled monolayer of alkanethiolates on gold and could therefore be analyzed by mass spectrometry. We found that the most reactive peptides had either a serine N-terminal to the tyrosine residue or another tyrosine in proximity of the reactive site. Conversely, peptides displaying the lowest conversion level contained a positive charged residue: histidine, lysine or arginine, where the lowest relative activity was reached with arginine and leucine as C- and N- terminal residues, respectively. This study provides an important example of how synthetic peptide libraries can accelerate the discovery and optimization of protein bioconjugation strategies.
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Monesi, Alessandro <1983&gt. « Sulfanyl Radical Addition to Alkynes : Revisiting an Old Reaction to Enter the Novel Realms of Green Chemistry, Bioconjugation, and Material Chemistry ». Doctoral thesis, Alma Mater Studiorum - Università di Bologna, 2012. http://amsdottorato.unibo.it/4555/1/Monesi_Alessandro_tesi.pdf.

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In the last decade considerable attention has been devoted to the rewarding use of Green Chemistry in various synthetic processes and applications. Green Chemistry is of special interest in the synthesis of expensive pharmaceutical products, where suitable adoption of “green” reagents and conditions is highly desirable. Our project especially focused in a search for new green radical processes which might also find useful applications in the industry. In particular, we have explored the possible adoption of green solvents in radical Thiol-Ene and Thiol-Yne coupling reactions, which to date have been normally performed in “ordinary” organic solvents such as benzene and toluene, with the primary aim of applying those coupling reactions to the construction of biological substrates. We have additionally tuned adequate reaction conditions which might enable achievement of highly functionalised materials and/or complex bioconjugation via homo/heterosequence. Furthermore, we have performed suitable theoretical studies to gain useful chemical information concerning mechanistic implications of the use of green solvents in the radical Thiol-Yne coupling reactions.
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Monesi, Alessandro <1983&gt. « Sulfanyl Radical Addition to Alkynes : Revisiting an Old Reaction to Enter the Novel Realms of Green Chemistry, Bioconjugation, and Material Chemistry ». Doctoral thesis, Alma Mater Studiorum - Università di Bologna, 2012. http://amsdottorato.unibo.it/4555/.

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In the last decade considerable attention has been devoted to the rewarding use of Green Chemistry in various synthetic processes and applications. Green Chemistry is of special interest in the synthesis of expensive pharmaceutical products, where suitable adoption of “green” reagents and conditions is highly desirable. Our project especially focused in a search for new green radical processes which might also find useful applications in the industry. In particular, we have explored the possible adoption of green solvents in radical Thiol-Ene and Thiol-Yne coupling reactions, which to date have been normally performed in “ordinary” organic solvents such as benzene and toluene, with the primary aim of applying those coupling reactions to the construction of biological substrates. We have additionally tuned adequate reaction conditions which might enable achievement of highly functionalised materials and/or complex bioconjugation via homo/heterosequence. Furthermore, we have performed suitable theoretical studies to gain useful chemical information concerning mechanistic implications of the use of green solvents in the radical Thiol-Yne coupling reactions.
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Poudel, Dhruba P. « Late-Stage Modification of Polyurethane Dendrimers Using Click Chemistry ». Miami University / OhioLINK, 2021. http://rave.ohiolink.edu/etdc/view?acc_num=miami1627490978861964.

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Li, Ronald Chuan-Teh. « Synthesis of polymer scaffolds for bioconjugation via chemoselective reactions ». Diss., Restricted to subscribing institutions, 2008. http://proquest.umi.com/pqdweb?did=1781842041&sid=3&Fmt=2&clientId=1564&RQT=309&VName=PQD.

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PACIFICO, Salvatore. « Sintesi di glicopeptidi mediante le reazioni tiol-ene/ino e studio della reattività di Umpolung di α-dichetoni ». Doctoral thesis, Università degli studi di Ferrara, 2013. http://hdl.handle.net/11392/2388912.

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It is well established that protein glycosylation, a bioorthogonal process, is a posttranslational modification that profoundly affects protein folding, stability, immunogenicity, and biological properties and activities. In this regard, while native O- and N-glycosidic bonds of glycopeptides are prone to hydrolytic cleavage by O- and N-glycosidases, synthetic C- and S-analogs are expected to be stable toward such enzymatic degradation. Therefore, much effort has been devoted in the last decades to synthesizing C- and S-glycosyl amino acids and their assembly in glycopeptides. They with these non-native linkages can be used as probes for biochemical studies and leads in drug discovery, such as, for example, vaccines. In the first part of this thesis project we developed two routes to synthesis of S-glycopeptides. One route consists of S-glycosyl amino acid synthesis from photoinduced addition of sugar thiols to alkenyl glycine (TEC) followed by incorporation of this amino acid into a peptide. The second route, that is, specific for a cysteine containing peptide such as glutathione, involves peptide S-homoallylation followed by TEC with sugar thiol. We also demonstrated the selective propargylation of cysteine-containing peptides followed by photoinduced thiol-yne coupling with glycosyl thiols as an effective one-pot two-step platform for the dual glycosylation of peptides. By this strategy, we also performed the sequential glycosylation and biotinylation of peptides. In recent years, N-heterocyclic carbenes (NHCs) have attracted considerable interest due to their unique features, which allow them to be used as ligands for organometallic catalysis, reagents in the synthesis of heterocycles, and efficient organocatalysts in umpolung transformations. In the latter sub-area of research many efforts have been devoted to the realization of highly stereoselective versions of the classical benzoin and Stetter reactions through optimal pre-catalyst design, to the discovery of new transformations, and to the umpolung of electrophiles alternative to aldehydes and pyruvates, mainly acylsilanes and Michael acceptors. In this thesis, our group has recently demonstrated the capability of linear and cyclic dialkyl α-diketones to undergo polarity reversal under thiazolium carbene catalysis in benzoin-type and Stetter reactions, and thus act as a novel class of acyl anion precursors. Contrarily, it has been observed that diaryl α-diketones do not undergo polarity reversal in the presence of (benzo)thiazolium carbenes but are engaged in a novel multicomponent reaction with water to efficiently give medicinally relevant 1,4-thiazin-3-one heterocycles. The umpolung reactivity of diaryl 1,2-diones, however, can be effectively triggered by different NHCs.
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Chan, On-yee, et 陳安怡. « Bioconjugation reactions of peptides and proteins mediated by manganese, ruthenium and gold compounds ». Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2010. http://hub.hku.hk/bib/B46539773.

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Chapitres de livres sur le sujet "Bioconjugation reaction"

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Chalker, Justin M. « Metal-Mediated Bioconjugation ». Dans Chemoselective and Bioorthogonal Ligation Reactions, 231–70. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527683451.ch8.

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Hein, Jason E. « [3+2]-Dipolar Cycloadditions in Bioconjugation ». Dans Chemoselective and Bioorthogonal Ligation Reactions, 37–66. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527683451.ch2.

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Budinova, Geisa A. L. G., Yutaro Mori et Noriho Kamiya. « Design of Artificial Supramolecular Protein Assemblies by Enzymatic Bioconjugation for Biocatalytic Reactions ». Dans Emerging Areas in Bioengineering, 93–103. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2018. http://dx.doi.org/10.1002/9783527803293.ch6.

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Hermanson, Greg T. « The Reactions of Bioconjugation ». Dans Bioconjugate Techniques, 229–58. Elsevier, 2013. http://dx.doi.org/10.1016/b978-0-12-382239-0.00003-0.

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Alberch, Laura, et Kevin J. Yarema. « Bioconjugation Reactions in Living Cells ». Dans Micro- and Nanoengineering of the Cell Surface, 43–62. Elsevier, 2014. http://dx.doi.org/10.1016/b978-1-4557-3146-6.00003-9.

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Actes de conférences sur le sujet "Bioconjugation reaction"

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Srinivasan, Balaji, Ju Seok Lee, Jacob Hohnbaum, Steve Tung et Jin-Woo Kim. « Performance evaluation of a pneumatic-based micromixer for bioconjugation reaction ». Dans 2010 5th IEEE International Conference on Nano/Micro Engineered and Molecular Systems (NEMS 2010). IEEE, 2010. http://dx.doi.org/10.1109/nems.2010.5592279.

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