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

Research output: Contribution to journalArticle

28 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)5037-5040
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume21
Issue number17
DOIs
StatePublished - Sep 1 2011

Fingerprint

Sialic Acids
N-acetylneuraminate lyase
Pasteurella multocida
Monosaccharides
N-Acetylneuraminic Acid
Pyruvic Acid
Polysaccharides
Carbon
Acids
8-O-methyl-N-glycolylneuraminic acid

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

Cite this

Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides. / Yu, Hai; Cao, Hongzhi; Tiwari, Vinod Kumar; Li, Yanhong; Chen, Xi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 17, 01.09.2011, p. 5037-5040.

Research output: Contribution to journalArticle

Yu, Hai ; Cao, Hongzhi ; Tiwari, Vinod Kumar ; Li, Yanhong ; Chen, Xi. / Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides. In: Bioorganic and Medicinal Chemistry Letters. 2011 ; Vol. 21, No. 17. pp. 5037-5040.
@article{917f68d756b44f718196d1cb31ada563,
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 = "9",
day = "1",
doi = "10.1016/j.bmcl.2011.04.083",
language = "English (US)",
volume = "21",
pages = "5037--5040",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "17",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=80051795743&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80051795743&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2011.04.083

DO - 10.1016/j.bmcl.2011.04.083

M3 - Article

C2 - 21592790

AN - SCOPUS:80051795743

VL - 21

SP - 5037

EP - 5040

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 17

ER -