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一锅法组装具有免疫增强活性的十四糖 GLSWA-1。

One-Pot Assembly of the Highly Branched Tetradecasaccharide from Glycan GLSWA-1 with Immune-Enhancing Activities.

机构信息

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research and Development of Natural Products, School of Pharmacy, Yunnan University, Kunming, Yunnan 650091, China.

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Kunming 650201, China.

出版信息

Org Lett. 2023 Oct 13;25(40):7395-7399. doi: 10.1021/acs.orglett.3c02898. Epub 2023 Oct 3.

Abstract

The highly branched tetradecasaccharide repeating unit and shorter sequences of GLSWA-1 with immune-enhancing activities from have been prepared via a one-pot glycan assembly strategy. The synthetic route features (1) orthogonal one-pot glycosylation on the basis of PVB glycosylation to streamline glycan synthesis avoiding such issues as aglycone transfer, (2) one-pot assembly of oligosaccharides with up to four different glycosyl linkages, and (3) modular and convergent [4+5+5] one-pot assembly of the highly branched tetradecasaccharide.

摘要

具有免疫增强活性的高度支化十四糖重复单元和较短序列 GLSAW-1 已通过一锅聚糖组装策略进行制备。该合成路线具有以下特点:(1)基于 PVB 糖基化的正交一锅糖苷化,以简化聚糖合成,避免糖苷转移等问题;(2)一锅组装多达四种不同糖苷键的寡糖;以及(3)高度支化十四糖的模块化和收敛式[4+5+5]一锅组装。

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