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糖基合成酶合成糖苷。

Synthesis of Glycosides by Glycosynthases.

机构信息

Institut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich, 52426 Jülich, Germany.

Forschungszentrum Jülich, IBG-1: Biotechnology, 52426 Jülich, Germany.

出版信息

Molecules. 2017 Aug 30;22(9):1434. doi: 10.3390/molecules22091434.

DOI:10.3390/molecules22091434
PMID:28867807
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6151457/
Abstract

The many advances in glycoscience have more and more brought to light the crucial role of glycosides and glycoconjugates in biological processes. Their major influence on the functionality and stability of peptides, cell recognition, health and immunity and many other processes throughout biology has increased the demand for simple synthetic methods allowing the defined syntheses of target glycosides. Additional interest in glycoside synthesis has arisen with the prospect of producing sustainable materials from these abundant polymers. Enzymatic synthesis has proven itself to be a promising alternative to the laborious chemical synthesis of glycosides by avoiding the necessity of numerous protecting group strategies. Among the biocatalytic strategies, glycosynthases, genetically engineered glycosidases void of hydrolytic activity, have gained much interest in recent years, enabling not only the selective synthesis of small glycosides and glycoconjugates, but also the production of highly functionalized polysaccharides. This review provides a detailed overview over the glycosylation possibilities of the variety of glycosynthases produced until now, focusing on the transfer of the most common glucosyl-, galactosyl-, xylosyl-, mannosyl-, fucosyl-residues and of whole glycan blocks by the different glycosynthase enzyme variants.

摘要

糖科学的诸多进展越来越多地揭示了糖苷和糖缀合物在生物过程中的关键作用。它们对肽的功能和稳定性、细胞识别、健康和免疫以及生物学中许多其他过程的主要影响,增加了对简单合成方法的需求,这些方法允许对目标糖苷进行定义合成。随着从这些丰富的聚合物中生产可持续材料的前景,人们对糖苷合成产生了额外的兴趣。与糖苷的费力化学合成相比,酶合成通过避免许多保护基策略的必要性,已被证明是一种很有前途的替代方法。在生物催化策略中,近年来,缺乏水解活性的基因工程糖苷酶——糖基合成酶引起了广泛关注,不仅能够选择性合成小糖苷和糖缀合物,还能够生产高度功能化的多糖。本文综述了迄今为止生产的各种糖基合成酶的糖基化可能性,重点介绍了不同糖基合成酶变体对最常见的葡萄糖基、半乳糖基、木糖基、甘露糖基、岩藻糖基残基以及整个聚糖块的转移。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/2c12dbb996e8/molecules-22-01434-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/202a8024330a/molecules-22-01434-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/26d45bb793b7/molecules-22-01434-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/3269780207c5/molecules-22-01434-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/347c0b0c05e1/molecules-22-01434-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/016a10281ed2/molecules-22-01434-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/7a5b21a22e75/molecules-22-01434-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/d82e84f19521/molecules-22-01434-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/919e66ba3eeb/molecules-22-01434-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/83a658d4a316/molecules-22-01434-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/aae8758ae0d2/molecules-22-01434-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/3a3e8d8a8907/molecules-22-01434-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/98d36f656805/molecules-22-01434-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/2c12dbb996e8/molecules-22-01434-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/202a8024330a/molecules-22-01434-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/26d45bb793b7/molecules-22-01434-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/3269780207c5/molecules-22-01434-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/347c0b0c05e1/molecules-22-01434-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/016a10281ed2/molecules-22-01434-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/7a5b21a22e75/molecules-22-01434-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/d82e84f19521/molecules-22-01434-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/919e66ba3eeb/molecules-22-01434-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/83a658d4a316/molecules-22-01434-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/aae8758ae0d2/molecules-22-01434-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/3a3e8d8a8907/molecules-22-01434-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/98d36f656805/molecules-22-01434-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6479/6151457/2c12dbb996e8/molecules-22-01434-sch013.jpg

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2
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Chem Sci. 2015 Aug 1;6(8):4636-4642. doi: 10.1039/c5sc00952a. Epub 2015 May 19.
3
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4
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JACS Au. 2022 Dec 7;3(1):47-61. doi: 10.1021/jacsau.2c00529. eCollection 2023 Jan 23.
5
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Biosci Biotechnol Biochem. 2017 Feb;81(2):283-291. doi: 10.1080/09168451.2016.1254532. Epub 2016 Nov 11.
8
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9
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Biotechnol Lett. 2017 Jan;39(1):157-162. doi: 10.1007/s10529-016-2230-0. Epub 2016 Oct 6.
10
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