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

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:21

Article

Yu, Hai¹  Cao, Hongzhi²  Tiwari, Vinod Kumar³  Li, Yanhong¹  Chen, Xi¹ 

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[2] Shandong Univ, Natl Glycoengn Res Ctr, Jinan 250012, Shandong, Peoples R China

[3] Banaras Hindu Univ, Fac Sci, Varanasi 221005, UP, India

关键词: Chemoenzymatic synthesis;    C8-modification;    Sialic acid;    Sialoside;    Sialyltransferase;   

DOI  :  10.1016/j.bmcl.2011.04.083

来源: Elsevier

【 摘 要 】

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-galactononulosonic 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, alpha 2-3- and alpha 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. (C) 2011 Elsevier Ltd. All rights reserved.

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