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Chemoenzymatic synthesis of C8-modified sialic acids and related ?2-3- and ?2-6-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, ?2-3- and ?2-6-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.

SUBMITTER: Yu H

PROVIDER: S-EPMC3156331 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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

Yu Hai H Cao Hongzhi H Tiwari Vinod Kumar VK Li Yanhong Y Chen Xi X

Bioorganic & medicinal chemistry letters 20110424 17

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 Kdn8Deox ...[more]

PMID: 21592790

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