Streamlined Chemoenzymatic Total Synthesis of Prioritized Ganglioside Cancer Antigens

Overview

Journal Org Biomol Chem

Publisher Royal Society of Chemistry

Specialties Biochemistry
Chemistry

Date 2018 May 24

PMID 29789847

Citations 16

Authors

Hai Yu

Abhishek Santra

Yanhong Li

John B McArthur

Tamashree Ghosh

Xiaoxiao Yang

Peng G Wang

Xi Chen

Affiliations

Soon will be listed here.

Abstract

A highly efficient streamlined chemoenzymatic strategy for total synthesis of four prioritized ganglioside cancer antigens GD2, GD3, fucosyl GM1, and GM3 from commercially available lactose and phytosphingosine is demonstrated. Lactosyl sphingosine (LacβSph) was chemically synthesized (on a 13 g scale), subjected to sequential one-pot multienzyme (OPME) glycosylation reactions with facile C18-cartridge purification, followed by improved acylation conditions to form target gangliosides, including fucosyl GM1 which has never been synthesized before.

Citing Articles

Comprehensive Modular Synthesis of Ganglioside Glycans and Evaluation of their Binding Affinities to Siglec-7 and Siglec-9.

Adak A, Tseng H, Chang S, Chiang Y, Lyu K, Lee Y Adv Sci (Weinh). 2024; 12(2):e2412815.

PMID: 39555730 PMC: 11727393. DOI: 10.1002/advs.202412815.

The Human Ganglioside Interactome in Live Cells Revealed Using Clickable Photoaffinity Ganglioside Probes.

Zhang G, Porter M, Awol A, Orsburn B, Canner S, Gray J J Am Chem Soc. 2024; 146(26):17801-17816.

PMID: 38887845 PMC: 11650378. DOI: 10.1021/jacs.4c03196.

A modular chemoenzymatic cascade strategy for the structure-customized assembly of ganglioside analogs.

Jin X, Cheng H, Chen X, Cao X, Xiao C, Ding F Commun Chem. 2024; 7(1):17.

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Enabling Chemoenzymatic Strategies and Enzymes for Synthesizing Sialyl Glycans and Sialyl Glycoconjugates.

Chen X Acc Chem Res. 2023; 57(2):234-246.

PMID: 38127793 PMC: 10795189. DOI: 10.1021/acs.accounts.3c00614.

Chemoenzymatic Synthesis of -Acetyl Analogues of 9--Acetylated b-Series Gangliosides.

Yu H, Zheng Z, Zhang L, Yang X, Varki A, Chen X Tetrahedron. 2023; 142.

PMID: 37981995 PMC: 10653377. DOI: 10.1016/j.tet.2023.133522.

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