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含有稀有α-d-岩藻糖胺（α-d-FucNAc）的C4115菌株O抗原五糖重复单元的合成。

Synthesis of the pentasaccharide repeating unit of the O-antigen from C4115 containing the rare α-d-FucNAc.

作者信息

Chaudhury Aritra, Mukhopadhyay Balaram

机构信息

Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata Mohanpur Nadia 741246 India

出版信息

RSC Adv. 2020 Jan 30;10(9):4942-4948. doi: 10.1039/c9ra09807k. eCollection 2020 Jan 29.

DOI:10.1039/c9ra09807k
PMID:35498329
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9049057/
Abstract

Total synthesis of the pentasaccharide repeating unit associated with the O-antigen of C4115 is reported. The synthesis of the said oligosaccharide was accomplished through rational protecting group manipulations on commercially available monosaccharides followed by stereoselective glycosylations either by activation of thioglycosides or glycosyl trichloroacetimidates and was found to be productive. Towards the synthesis of the rare sugar unit, α-d-FucNAc in this case, it was established that the methoxymethyl (MOM) group is advantageous over the earlier reported tetrahydro pyran (THP) protection. The effect of MOM-protection was successfully tested for the synthesis of a rare sugar synthon which can serve as a precursor to the rare d-fucosamine residue.

摘要

报道了与C4115的O抗原相关的五糖重复单元的全合成。所述寡糖的合成是通过对市售单糖进行合理的保护基操作，然后通过硫代糖苷或糖基三氯乙酰亚胺酯的活化进行立体选择性糖基化来完成的，并且发现该方法是有效的。对于在这种情况下的稀有糖单元α-d-FucNAc的合成，已确定甲氧基甲基（MOM）基团比先前报道的四氢吡喃（THP）保护更具优势。成功测试了MOM保护对稀有糖合成子合成的影响，该合成子可作为稀有d-岩藻糖胺残基的前体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/d15cecaf41d6/c9ra09807k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/294f8fc988bf/c9ra09807k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/c80ec756b212/c9ra09807k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/d6d00f591201/c9ra09807k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/a54127407b17/c9ra09807k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/d15cecaf41d6/c9ra09807k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/294f8fc988bf/c9ra09807k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/c80ec756b212/c9ra09807k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/d6d00f591201/c9ra09807k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/a54127407b17/c9ra09807k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae97/9049057/d15cecaf41d6/c9ra09807k-s3.jpg

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