Appraisal of an oligomerization behavior of unprotected carbohydrates induced by phosphorus reagent

被引：9

作者：

Yuan, Hang ^{[1
]}

Yang, Xu ^{[1
]}

Chen, Peng ^{[1
]}

Liu, Yan ^{[1
]}

Tang, Guo ^{[1
]}

Zhao, Yufen ^{[1
,2
]}

机构：

[1] Xiamen Univ, Dept Chem Biol, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Peoples R China

[2] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

来源：

SCIENCE CHINA-CHEMISTRY | 2018年 / 61卷 / 02期

基金：

中国国家自然科学基金;

关键词：

organic phosphorus activation; oligosaccharide; oligomerization; one-pot unprotected synthesis; AUTOMATED OLIGOSACCHARIDE SYNTHESIS; PRESSURE LIQUID-CHROMATOGRAPHY; LIGHT-SCATTERING DETECTION; SOLID-PHASE SYNTHESIS; ACETYLATED OLIGOSACCHARIDES; MONOSACCHARIDES; GLYCOSYLATION; SEPARATION; LINKAGE; CELLS;

D O I：

10.1007/s11426-017-9165-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this article, a novel oligomerization behavior of unprotected monosaccharides was discovered in a one-pot reaction induced by phosphorus reagent at room temperature. The inherent characteristics of the oligomerization reaction were dissected in detail by mass spectrometry based method combined with NMR technology. It was found that the main glycosidic bonding pattern is (1 -> 6) linkage with 66% regioselectivity for each step. The ratio of alpha-(1 -> 6) and beta-(1 -> 6) glycosidic bonds formed is around 1:1. The reactivity of 1-OH group from aldoses and the driving force from penta-coordinated phosphorus intermediates are the two critical factors for the oligomerization, according to the monitoring experiments by ESI-MS and NMR. Besides, the oligomerization reaction has good compatibility for various aldoses and could expand to O-glycosylated modification of peptides in vitro. The above results will provide a novel enlightenment to develop more convenient and higher-efficient methods for the synthesis of oligosaccharide library.

引用

页码：243 / 250

页数：8

共 21 条

[21] Phosphorus incorporation-induced adsorption behavior modulation for carbon cathodes enables ultrastable and high-energy aqueous Zn-ion hybrid capacitors
Lai Yu
Xiaoyue He
Rong Liu
Guanglin Wan
Xinyi Ma
Anqiang Pan
Liang Shi
Genqiang Zhang
Science China Chemistry, 2025, 68 (3) : 900 - 907

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