Literature DB >> 28824290

A General Chemoenzymatic Strategy for the Synthesis of Glycosphingolipids.

Yunpeng Liu1,2, Liuqing Wen2, Lei Li2, Madhusudhan Reddy Gadi2, Wanyi Guan2, Kenneth Huang2, Zhongying Xiao2, Mohui Wei2, Cheng Ma2, Qing Zhang2, Hai Yu3, Xi Chen3, Peng George Wang1,2, Junqiang Fang1.   

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.

Entities:  

Keywords:  N-phenyltrifluoroacetimidate; chemoenzymatic; enzymatic synthesis; glycosphingolipids; glycosylation

Year:  2016        PMID: 28824290      PMCID: PMC5560440          DOI: 10.1002/ejoc.201600950

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  43 in total

1.  PmST2: a novel Pasteurella multocida glycolipid α2-3-sialyltransferase.

Authors:  Vireak Thon; Kam Lau; Hai Yu; Bao K Tran; Xi Chen
Journal:  Glycobiology       Date:  2011-04-21       Impact factor: 4.313

Review 2.  Glycosylation with glycosyl N-phenyltrifluoroacetimidates (PTFAI) and a perspective of the future development of new glycosylation methods.

Authors:  Biao Yu; Jiansong Sun
Journal:  Chem Commun (Camb)       Date:  2010-05-26       Impact factor: 6.222

3.  A multifunctional Pasteurella multocida sialyltransferase: a powerful tool for the synthesis of sialoside libraries.

Authors:  Hai Yu; Harshal Chokhawala; Rebekah Karpel; Hui Yu; Bingyuan Wu; Jianbo Zhang; Yingxin Zhang; Qiang Jia; Xi Chen
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

4.  Glycosynthase-mediated synthesis of glycosphingolipids.

Authors:  Mark D Vaughan; Karl Johnson; Shawn DeFrees; Xiaoping Tang; R Antony J Warren; Stephen G Withers
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

5.  Bacterial homologue of human blood group A transferase.

Authors:  Wen Yi; Jie Shen; Guangyan Zhou; Jianjun Li; Peng George Wang
Journal:  J Am Chem Soc       Date:  2008-10-09       Impact factor: 15.419

6.  Gangliosides prevent glutamate and kainate neurotoxicity in primary neuronal cultures of neonatal rat cerebellum and cortex.

Authors:  M Favaron; H Manev; H Alho; M Bertolino; B Ferret; A Guidotti; E Costa
Journal:  Proc Natl Acad Sci U S A       Date:  1988-10       Impact factor: 11.205

7.  Efficient synthesis of D-erythro-sphingosine and D-erythro-azidosphingosine from D-ribo-phytosphingosine via a cyclic sulfate intermediate.

Authors:  Sanghee Kim; Sukjin Lee; Taeho Lee; Hyojin Ko; Deukjoon Kim
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

Review 8.  Enzymatic synthesis of oligosaccharides and neoglycoconjugates.

Authors:  Takeomi Murata; Taichi Usui
Journal:  Biosci Biotechnol Biochem       Date:  2006-05       Impact factor: 2.043

9.  Ganglioside expression in lung cancer cell lines.

Authors:  R Fuentes; R Allman; M D Mason
Journal:  Lung Cancer       Date:  1997-08       Impact factor: 5.705

10.  Substrate promiscuity of N-acetylhexosamine 1-kinases.

Authors:  Yanhong Li; Hai Yu; Yi Chen; Kam Lau; Li Cai; Hongzhi Cao; Vinod Kumar Tiwari; Jingyao Qu; Vireak Thon; Peng George Wang; Xi Chen
Journal:  Molecules       Date:  2011-07-28       Impact factor: 4.411

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  4 in total

Review 1.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
Journal:  J Am Chem Soc       Date:  2019-02-18       Impact factor: 15.419

2.  Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens.

Authors:  Hai Yu; Abhishek Santra; Yanhong Li; John B McArthur; Tamashree Ghosh; Xiaoxiao Yang; Peng G Wang; Xi Chen
Journal:  Org Biomol Chem       Date:  2018-06-06       Impact factor: 3.876

3.  Chemoenzymatic modular assembly of O-GalNAc glycans for functional glycomics.

Authors:  Shuaishuai Wang; Congcong Chen; Madhusudhan Reddy Gadi; Varma Saikam; Ding Liu; He Zhu; Roni Bollag; Kebin Liu; Xi Chen; Fengshan Wang; Peng George Wang; Peixue Ling; Wanyi Guan; Lei Li
Journal:  Nat Commun       Date:  2021-06-11       Impact factor: 14.919

4.  Chemoenzymatic Total Synthesis of GM3 Gangliosides Containing Different Sialic Acid Forms and Various Fatty Acyl Chains.

Authors:  Hai Yu; Madhusudhan Reddy Gadi; Yuanyuan Bai; Libo Zhang; Lei Li; Jun Yin; Peng G Wang; Xi Chen
Journal:  J Org Chem       Date:  2021-06-21       Impact factor: 4.198

  4 in total

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