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Issue 22, 2018
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Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

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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

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Supplementary files

Article information


Submitted
09 May 2018
Accepted
10 May 2018
First published
14 May 2018

Org. Biomol. Chem., 2018,16, 4076-4080
Article type
Communication
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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