Issue 22, 2018

Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

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.

Graphical abstract: Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

Supplementary files

Article information

Article type
Communication
Submitted
09 Mot 2018
Accepted
10 Mot 2018
First published
14 Mot 2018

Org. Biomol. Chem., 2018,16, 4076-4080

Author version available

Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

H. Yu, A. Santra, Y. Li, J. B. McArthur, T. Ghosh, X. Yang, P. G. Wang and X. Chen, Org. Biomol. Chem., 2018, 16, 4076 DOI: 10.1039/C8OB01087K

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