Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens

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

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)4076-4080
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number22
DOIs
StatePublished - Jan 1 2018

Fingerprint

lactose
cartridges
acylation
phytosphingosine
Gangliosides
antigens
purification
cancer
Glycosylation
Antigens
Acylation
Sphingosine
Lactose
synthesis
Purification
Neoplasms
fucosyl GM1 ganglioside

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens. / Yu, Hai; Santra, Abhishek; Li, Yanhong; McArthur, John B.; Ghosh, Tamashree; Yang, Xiaoxiao; Wang, Peng G.; Chen, Xi.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 22, 01.01.2018, p. 4076-4080.

Research output: Contribution to journalArticle

Yu, H, Santra, A, Li, Y, McArthur, JB, Ghosh, T, Yang, X, Wang, PG & Chen, X 2018, 'Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens', Organic and Biomolecular Chemistry, vol. 16, no. 22, pp. 4076-4080. https://doi.org/10.1039/c8ob01087k
Yu, Hai ; Santra, Abhishek ; Li, Yanhong ; McArthur, John B. ; Ghosh, Tamashree ; Yang, Xiaoxiao ; Wang, Peng G. ; Chen, Xi. / Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens. In: Organic and Biomolecular Chemistry. 2018 ; Vol. 16, No. 22. pp. 4076-4080.
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