One-pot three-enzyme chemoenzymatic approach to the synthesis of sialosides containing natural and non-natural functionalities

Hai Yu, Harshal A. Chokhawala, Shengshu Huang, Xi Chen

Research output: Contribution to journalArticle

98 Citations (Scopus)

Abstract

Chemoenzymatic synthesis, which combines the flexibility of chemical synthesis and the high selectivity of enzymatic synthesis, is a powerful approach to obtain complex carbohydrates. It is a preferred method for synthesizing sialic acid-containing structures, including those with diverse naturally occurring and non-natural sialic acid forms, different sialyl linkages and different glycans that link to the sialic acid. Starting from N-acetylmannosamine, mannose or their chemically or enzymatically modified derivatives, sialic acid aldolase-catalyzed condensation reaction leads to the formation of sialic acids and their derivatives. These compounds are subsequently activated by a CMP-sialic acid synthetase and transferred to a wide range of suitable acceptors by a suitable sialyltransferase for the formation of sialosides containing natural and non-natural functionalities. The three-enzyme coupled synthesis of sialosides can be carried out in one pot without the isolation of intermediates. The time for synthesis is 4-18 h. Purification and characterization of the product can be completed within 2-3 d.

Original languageEnglish (US)
Pages (from-to)2485-2492
Number of pages8
JournalNature Protocols
Volume1
Issue number5
DOIs
StatePublished - Dec 2006

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N-Acetylneuraminic Acid
N-acetylneuraminate lyase
N-Acylneuraminate Cytidylyltransferase
Enzymes
Sialyltransferases
Sialic Acids
Mannose
Polysaccharides
Derivatives
Carbohydrates
Condensation reactions
Purification

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

One-pot three-enzyme chemoenzymatic approach to the synthesis of sialosides containing natural and non-natural functionalities. / Yu, Hai; Chokhawala, Harshal A.; Huang, Shengshu; Chen, Xi.

In: Nature Protocols, Vol. 1, No. 5, 12.2006, p. 2485-2492.

Research output: Contribution to journalArticle

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