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. 2018 Jun 6;16(22):4076-4080.
doi: 10.1039/c8ob01087k.

Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

Hai Yu  1 , Abhishek Santra, Yanhong Li, John B McArthur, Tamashree Ghosh, Xiaoxiao Yang, Peng G Wang, Xi Chen
Affiliations

Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

Hai Yu et al. Org Biomol Chem. .

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.

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Conflict of interest statement

Conflicts of interest

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1
Structures of prioritized ganglioside cancer antigens GM3 (1), fucosyl GM1 (2), GD3 (3), and GD2 (4).
Scheme 1
Scheme 1
Gram-scale (1.44 g) synthesis of GM3βSph (6) by one-pot multienzyme (OPME) sialylation of LacβSph (5).
Scheme 2
Scheme 2
Sequential one-pot multienzyme (OPME) synthesis of Fuc-GM1βSph (9) from GM3βSph (6).
Scheme 3
Scheme 3
Sequential one-pot multienzyme (OPME) synthesis of GD3βSph (10) and GD2βSph (11) from GM3βSph (6).
See this image and copyright information in PMC

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