C8 修饰的唾液酸及其相关的 α2-3-和 α2-6-连接的唾液糖的酶促化学合成。
Chemoenzymatic synthesis of C8-modified sialic acids and related α2-3- and α2-6-linked sialosides.
机构信息
Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, United States.
出版信息
Bioorg Med Chem Lett. 2011 Sep 1;21(17):5037-40. doi: 10.1016/j.bmcl.2011.04.083. Epub 2011 Apr 24.
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.
摘要
天然存在的 8-O-甲基化唾液酸，包括 8-O-甲基-N-乙酰神经氨酸和 8-O-甲基-N-羟乙酰神经氨酸，以及 8-O-甲基-2-酮-3-脱氧-d-甘油-d-半乳糖-壬酮酸（Kdn8Me）和 8-脱氧-Kdn，是从相应的 5-O-修饰的六碳单糖和丙酮酸使用从多杀巴斯德氏菌 P-1059 株（PmNanA）克隆的唾液酸醛缩酶合成的。此外，还使用一锅多酶法合成了含有 Neu5Ac8Me 和 Kdn8Deoxy 的α2-3-和α2-6 连接的唾液酰基三糖。本报告的策略为生产含有各种 C8 修饰的唾液酸的聚糖提供了一种有效的方法，用于生物学评价。
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