Synthesis of N-glycolylneuraminic acid (Neu5Gc) and its glycosides

Anoopjit Singh Kooner, Hai Yu, Xi Chen

Research output: Contribution to journalReview article

1 Citation (Scopus)

Abstract

Sialic acids constitute a family of negatively charged structurally diverse monosaccharides that are commonly presented on the termini of glycans in higher animals and some microorganisms. In addition to N-acetylneuraminic acid (Neu5Ac), N-glycolyl neuraminic acid (Neu5Gc) is among the most common sialic acid forms in nature. Nevertheless, unlike most animals, human cells loss the ability to synthesize Neu5Gc although Neu5Gc-containing glycoconjugates have been found on human cancer cells and in various human tissues due to dietary incorporation of Neu5Gc. Some pathogenic bacteria also produce Neu5Ac and the corresponding glycoconjugates but Neu5Gc-producing bacteria have yet to be found. In addition to Neu5Gc, more than 20 Neu5Gc derivatives have been found in non-human vertebrates. To explore the biological roles of Neu5Gc and its naturally occurring derivatives as well as the corresponding glycans and glycoconjugates, various chemical and enzymatic synthetic methods have been developed to obtain a vast array of glycosides containing Neu5Gc and/or its derivatives. Here we provide an overview on various synthetic methods that have been developed. Among these, the application of highly efficient one-pot multienzyme (OPME) sialylation systems in synthesizing compounds containing Neu5Gc and derivatives has been proven as a powerful strategy.

Original languageEnglish (US)
Article number2004
JournalFrontiers in immunology
Volume10
Issue numberAUG
DOIs
StatePublished - Jan 1 2019

Fingerprint

Glycoconjugates
Glycosides
N-Acetylneuraminic Acid
Polysaccharides
Neuraminic Acids
Sialic Acids
Bacteria
Monosaccharides
Vertebrates
N-glycolylneuraminic acid
Neoplasms

Keywords

  • Chemical synthesis
  • Chemoenzymatic synthesis
  • Neu5Gc
  • Sialic acid
  • Sialoside

ASJC Scopus subject areas

  • Immunology and Allergy
  • Immunology

Cite this

Synthesis of N-glycolylneuraminic acid (Neu5Gc) and its glycosides. / Kooner, Anoopjit Singh; Yu, Hai; Chen, Xi.

In: Frontiers in immunology, Vol. 10, No. AUG, 2004, 01.01.2019.

Research output: Contribution to journalReview article

Kooner, Anoopjit Singh ; Yu, Hai ; Chen, Xi. / Synthesis of N-glycolylneuraminic acid (Neu5Gc) and its glycosides. In: Frontiers in immunology. 2019 ; Vol. 10, No. AUG.
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