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立体选择性化学糖基化反应的最新进展

Recent Advances in Stereoselective Chemical -Glycosylation Reactions.

作者信息

Mukherjee Mana Mohan, Ghosh Rina, Hanover John A

机构信息

Laboratory of Cell and Molecular Biology, NIDDK, National Institutes of Health, Bethesda, MD, United States.

Department of Chemistry, Jadavpur University, Kolkata, India.

出版信息

Front Mol Biosci. 2022 Jun 14;9:896187. doi: 10.3389/fmolb.2022.896187. eCollection 2022.

DOI:10.3389/fmolb.2022.896187
PMID:35775080
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9237389/
Abstract

Carbohydrates involving glycoconjugates play a pivotal role in many life processes. Better understanding toward glycobiological events including the structure-function relationship of these biomolecules and for diagnostic and therapeutic purposes including tailor-made vaccine development and synthesis of structurally well-defined oligosaccharides (OS) become important. Efficient chemical glycosylation in high yield and stereoselectivity is however challenging and depends on the fine tuning of a protection profile to get matching glycosyl donor-acceptor reactivity along with proper use of other important external factors like catalyst, solvent, temperature, activator, and additive. So far, many glycosylation methods have been reported including several reviews also. In the present review, we will concentrate our discussion on the recent trend on α- and β-selective glycosylation reactions reported during the past decade.

摘要

涉及糖缀合物的碳水化合物在许多生命过程中起着关键作用。更好地理解糖生物学事件,包括这些生物分子的结构 - 功能关系,以及用于诊断和治疗目的,包括定制疫苗开发和合成结构明确的寡糖(OS)变得很重要。然而,高效的化学糖基化反应要实现高产率和立体选择性具有挑战性,这取决于对保护策略的精细调整,以使糖基供体 - 受体反应性相匹配,同时正确使用其他重要的外部因素,如催化剂、溶剂、温度、活化剂和添加剂。到目前为止,已经报道了许多糖基化方法,也有几篇综述。在本综述中,我们将集中讨论过去十年中报道的α - 和β - 选择性糖基化反应的最新趋势。

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2
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J Org Chem. 2022 Mar 4;87(5):3718-3729. doi: 10.1021/acs.joc.1c02650. Epub 2022 Jan 21.
3
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Molecules. 2025 Jan 5;30(1):185. doi: 10.3390/molecules30010185.
4
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Molecules. 2024 Dec 31;30(1):120. doi: 10.3390/molecules30010120.
5
ZnI-Mediated -Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in -Selective Glycosylations.碘化锌介导的各种受限糖基供体的α-糖基化反应:α-选择性糖基化反应的最新进展
Molecules. 2024 Oct 4;29(19):4710. doi: 10.3390/molecules29194710.
6
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Chembiochem. 2024 Sep 16;25(18):e202400391. doi: 10.1002/cbic.202400391. Epub 2024 Jul 30.
7
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8
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9
Enzymatic properties of UDP-glycosyltransferase 89B1 from radish and modulation of enzyme catalytic activity via loop region mutation.萝卜 UDP-糖基转移酶 89B1 的酶学性质及其通过环区突变对酶催化活性的调节。
PLoS One. 2024 Feb 28;19(2):e0299755. doi: 10.1371/journal.pone.0299755. eCollection 2024.
10
Comparison of glycosyl donors: a supramer approach.糖基供体的比较:一种超分子方法。
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4
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5
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6
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8
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