Gold(I)-catalyzed synthesis of β-Kdo glycosides using Kdo ortho-hexynylbenzoate as donor

Xuemeng Mi; Qixin Lou; Wenjing Fan; Liqin Zhuang; You Yang

doi:10.1016/j.carres.2017.04.021

Gold(I)-catalyzed synthesis of β-Kdo glycosides using Kdo ortho-hexynylbenzoate as donor

Carbohydr Res. 2017 Aug 7:448:161-165. doi: 10.1016/j.carres.2017.04.021. Epub 2017 Apr 28.

Authors

Xuemeng Mi¹, Qixin Lou¹, Wenjing Fan¹, Liqin Zhuang¹, You Yang²

Affiliations

¹ Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.
² Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China. Electronic address: yangyou@ecust.edu.cn.

PMID: 28478910
DOI: 10.1016/j.carres.2017.04.021

Abstract

A gold(I)-catalyzed glycosylation of Kdo with glycosyl ortho-hexynylbenzoate as donor is reported. The couplings of Kdo ortho-hexynylbenzoate with a set of alcohols promoted by PPh₃AuOTf afford Kdo glycosides with good β-selectivities. This glycosylation method allows for the synthesis of β-Kdo monosaccharide with a C5 linker at the reducing end for subsequent conjugation to carrier proteins and arrays.

Keywords: Glycosyl ortho-hexynylbenzoate; Glycosylation; Gold; Kdo; Synthetic methods.

MeSH terms

Benzoic Acid / chemistry*
Catalysis
Chemistry Techniques, Synthetic
Glycosides / chemical synthesis*
Glycosides / chemistry*
Glycosylation
Gold / chemistry*

Substances

Glycosides
Gold
Benzoic Acid