Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides

Hai Yu; Hongzhi Cao; Vinod Kumar Tiwari; Yanhong Li; Xi Chen

doi:10.1016/j.bmcl.2011.04.083

Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides

Hai Yu, Hongzhi Cao, Vinod Kumar Tiwari, Yanhong Li, Xi Chen

Chemistry

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.

Original language	English (US)
Pages (from-to)	5037-5040
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2011.04.083
State	Published - Sep 1 2011

Keywords

C8-modification
Chemoenzymatic synthesis
Sialic acid
Sialoside
Sialyltransferase

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

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title = "Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides",

abstract = "Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.",

keywords = "C8-modification, Chemoenzymatic synthesis, Sialic acid, Sialoside, Sialyltransferase",

author = "Hai Yu and Hongzhi Cao and Tiwari, {Vinod Kumar} and Yanhong Li and Xi Chen",

year = "2011",

month = sep,

day = "1",

doi = "10.1016/j.bmcl.2011.04.083",

language = "English (US)",

volume = "21",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides

AU - Yu, Hai

AU - Cao, Hongzhi

AU - Tiwari, Vinod Kumar

AU - Li, Yanhong

AU - Chen, Xi

PY - 2011/9/1

Y1 - 2011/9/1

N2 - Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.

AB - Naturally occurring 8-O-methylated sialic acids, including 8-O-methyl-N-acetylneuraminic acid and 8-O-methyl-N-glycolylneuraminic acid, along with 8-O-methyl-2-keto-3-deoxy-d-glycero-d-galacto-nonulosonic acid (Kdn8Me) and 8-deoxy-Kdn were synthesized from corresponding 5-O-modified six-carbon monosaccharides and pyruvate using a sialic acid aldolase cloned from Pasteurella multocida strain P-1059 (PmNanA). In addition, α2-3- and α2-6-linked sialyltrisaccharides containing Neu5Ac8Me and Kdn8Deoxy were also synthesized using a one-pot multienzyme approach. The strategy reported here provides an efficient approach to produce glycans containing various C8-modified sialic acids for biological evaluations.

KW - C8-modification

KW - Chemoenzymatic synthesis

KW - Sialic acid

KW - Sialoside

KW - Sialyltransferase

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