A General Chemoenzymatic Strategy for the Synthesis of Glycosphingolipids. Issue 25 (16th August 2016)

• Record Type: Journal Article
• Authors: Liu, Yunpeng; Wen, Liuqing; Li, Lei; Gadi, Madhusudhan Reddy; Guan, Wanyi; Huang, Kenneth; Xiao, Zhongying; Wei, Mohui; Ma, Cheng; Zhang, Qing; Yu, Hai; Chen, Xi; Wang, Peng George; Fang, Junqiang
• Is Part Of: European journal of organic chemistry. Issue 25(2016)
• Page Start: 4315
• Page End: 4320
• Publication Date: 2016-08-16
• Subjects: Enzyme catalysis -- Glycosylation -- Glycosphingolipids -- Medicinal chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600950
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A concise, prototypical, and stereoselective strategy for the synthesis of therapeutically and immunologically significant glycosphingolipids has been developed. This strategy provides a universal platform for glycosphingolipid synthesis by block coupling of enzymatically prepared free oligosaccharideglycans to lipids using glycosyl N ‐phenyltrifluoroacetimidates as efficient activated intermediates. As demonstrated here, two different types of glycosphingolipids were obtained in excellent yields using the method. Abstract : Firstly, three oligosaccharides were prepared by a one‐pot multienzyme system (OPME). Subsequently, the oligosaccharides were easily converted to N ‐phenyltrifluoroacetimidate donors using benzoyl as protecting group, followed by block coupling of enzymatically prepared sugar parts to lipid acceptors with TMSOTf as a promotor to produce corresponding GSLs.