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.

• Authors: Hai Yu, Abhishek Santra, Yanhong Li, John B McArthur, Tamashree Ghosh, Xiaoxiao Yang, Peng G Wang, Xi Chen
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 16 Issue 22 Pg. 4076-4080 (06 06 2018) ISSN: 1477-0539 [Electronic] England
• PMID: 29789847 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• Antigens, Neoplasm
• G(M3) Ganglioside
• G(M1) Ganglioside
• fucosyl GM1 ganglioside
• phytosphingosine
• Lactose
• Sphingosine

Topics

• Antigens, Neoplasm (chemistry)
• G(M1) Ganglioside (analogs & derivatives, chemical synthesis)
• G(M3) Ganglioside (chemical synthesis)
• Glycosylation
• Lactose (chemistry)
• Sphingosine (analogs & derivatives, chemistry)