Adaptable synthesis of C-lactosyl glycoclusters and their binding properties with galectin-3

Wang Yao; Meng-jie Xia; Xiang-bao Meng; Qing Li; Zhong-jun Li

doi:10.1039/c4ob01374c

Adaptable synthesis of C-lactosyl glycoclusters and their binding properties with galectin-3

Org Biomol Chem. 2014 Nov 7;12(41):8180-95. doi: 10.1039/c4ob01374c. Epub 2014 Sep 3.

Authors

Wang Yao¹, Meng-jie Xia, Xiang-bao Meng, Qing Li, Zhong-jun Li

Affiliation

¹ The State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, Beijing 100191, P R China. qli@bjmu.edu.cn zjli@bjmu.edu.cn.

PMID: 25183239
DOI: 10.1039/c4ob01374c

Abstract

We report here the syntheses of mono- to tetravalent glycoclusters containing 1-methylene-C-β-lactose. The 1-methylene-C-β-lactose moiety has been synthesized from octa-acetyl-β-lactose using the key carbonyl insertion reaction and linked to a series of alkynlated scaffolds via CuAAC reaction to afford mono- to tetravalent glycoclusters. The binding affinities of the final products to galectin-3 were found in the range of 10-100 μM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Binding Sites
Galectin 3 / chemistry
Galectin 3 / metabolism*
Glycoconjugates / chemical synthesis*
Glycoconjugates / chemistry
Glycoconjugates / metabolism*
Lactose / chemistry*
Molecular Structure

Substances

Galectin 3
Glycoconjugates
Lactose