化学酶法合成一种在C-4位具有氨甲酰甲基的N-乙酰神经氨酸类似物作为流感病毒唾液酸酶的抑制剂。
Chemoenzymatic synthesis of an N-acetylneuraminic acid analogue having a carbamoylmethyl group at C-4 as an inhibitor of sialidase from influenza virus.
作者信息
Ikeda K, Kimura F, Sano K, Suzuki Y, Achiwa K
机构信息
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
出版信息
Carbohydr Res. 1998 Nov;312(4):183-9. doi: 10.1016/s0008-6215(98)00258-4.
5,9-Diacetamido-2,6-anhydro-O-4-carbamoylmethyl-3,5,9-trideo xy-D-glycero- D-galacto-non-2-enonic acid (1) was synthesized via a key intemediate 2 through the Neu5Ac aldolase [E.C.4.1.3.3]-catalyzed aldol reaction of 2-acetamido-2,6-dideoxy-6-azido-D-glucose with sodium pyruvate operating under alkaline conditions (pH 10.5) in order to accelerate epimerization C-2 of N-acetyl-D-glucosamine (D-GlcNAc) derivatives. Compound 1 showed inhibitory activity against sialidase.
5,9-二乙酰氨基-2,6-脱水-O-4-氨甲酰甲基-3,5,9-三脱氧-D-甘油-D-半乳糖-壬-2-烯酸（1）通过关键中间体2，经由Neu5Ac醛缩酶[E.C.4.1.3.3]催化2-乙酰氨基-2,6-二脱氧-6-叠氮基-D-葡萄糖与丙酮酸钠在碱性条件（pH 10.5）下的羟醛反应合成，以加速N-乙酰-D-葡萄糖胺（D-GlcNAc）衍生物C-2位的差向异构化。化合物1显示出对唾液酸酶的抑制活性。
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