Towards a Systematic Understanding of the Influence of Temperature on Glycosylation Reactions
TLDR
Isothermal glycosylation below the activation temperature halved the equivalents of building block required in comparison to the standard 'ramp' regime used in solution- and solid-phase oligosaccharide synthesis to-date.Abstract:
Abstract Glycosidic bond formation is a continual challenge for practitioners. Aiming to enhance the reproducibility and efficiency of oligosaccharide synthesis, we studied the relationship between glycosyl donor activation and reaction temperature. A novel semi‐automated assay revealed diverse responses of members of a panel of thioglycosides to activation at various temperatures. The patterns of protecting groups and the thiol aglycon combine to cause remarkable differences in temperature sensitivity among glycosyl donor building blocks. We introduce the concept of donor activation temperature to capture experimental insights, reasoning that glycosylations performed below this reference temperature evade deleterious side reactions. Activation temperatures enable a simplified temperature treatment and facilitate optimization of glycosyl donor usage. Isothermal glycosylation below the activation temperature halved the equivalents of building block required in comparison to the standard “ramp” regime used in solution‐ and solid‐phase oligosaccharide synthesis to‐date.read more
Citations
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Automated solution-phase multiplicative synthesis of complex glycans up to a 1,080-mer
TL;DR: In this article , an automated solution-phase multiplicative synthesis of complex glycans enabled by preactivation-based, multicomponent, one-pot glycosylation and continuous multiplying amplification is presented.
Journal ArticleDOI
Towards a Systematic Understanding of the Influence of Temperature on Glycosylation Reactions
TL;DR: Isothermal glycosylation below the activation temperature halved the equivalents of building block required in comparison to the standard 'ramp' regime used in solution- and solid-phase oligosaccharide synthesis to-date.
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Automated Chemical <scp>Solid‐Phase</scp> Synthesis of Glycans
TL;DR: In this article , the authors highlight the key advances in the field of automated chemical solid-phase synthesis, especially in Automated Glycan Assembly (AGA), and the synthesis of representative glycans based on AGA is also described.
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Glycosaminoglycans: What Remains To Be Deciphered?
Serge Pérez,Olga Makshakova,Jesús Angulo,Emiliano Bedini,Antonella Bisio,José L. de Paz,Elisa Fadda,Marco Guerrini,Michal Hricovíni,Miloš Hricovíni,Frédérique Lisacek,Pedro M. Nieto,Kevin Pagel,Giulia Paiardi,Ralf P. Richter,Sergey A. Samsonov,Romain A. Vivès,Dragana Nikitovic,Sylvie Ricard Blum +18 more
TL;DR: Glycosaminoglycans (GAGs) are complex polysaccharides exhibiting a vast structural diversity and fulfilling various functions mediated by thousands of interactions in the extracellular matrix, at the cell surface, and within the cells where they have been detected in the nucleus as mentioned in this paper .
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Recent Advances in Stereoselective Chemical O-Glycosylation Reactions
TL;DR: The present review will concentrate the discussion on the recent trend on α- and β-selective glycosylation reactions reported during the past decade.
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Why are the hydroxy groups of partially protected N-acetylglucosamine derivatives such poor glycosyl acceptors, and what can be done about it? A comparative study of the reactivity of N-acetyl-, N-phthalimido-, and 2-azido-2-deoxy-glucosamine derivatives in glycosylation. 2-Picolinyl ethers as reactivity-enhancing replacements for benzyl ethers.
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