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[2-乙酰氨基-1,4-亚氨基-1,2,4-三脱氧-D-半乳糖醇的合成及对人溶酶体β-己糖胺酶A的竞争性抑制作用]

[Synthesis of 2-acetamido-1,4-imino-1,2,4-tridesoxy-D-galactitol and competitive inhibition of human lysosomal beta-hexosaminidase A].

作者信息

Liessem B, Giannis A, Sandhoff K, Nieger M

机构信息

Institut für Organische Chemie und Biochemie der Universität Bonn, Deutschland.

出版信息

Carbohydr Res. 1993 Dec 16;250(1):19-30. doi: 10.1016/0008-6215(93)84151-u.

DOI:10.1016/0008-6215(93)84151-u
PMID:8143290
Abstract

The synthesis of 2-acetamido-1,4-imino-1,2,4-trideoxy-D-galactitol (1; 2-acetamido-4-amino-1,4-anhydro-2,4-dideoxy-D-galactitol) by two different routes starting from 2-acetamido-2-deoxy-D-glucose is described. Compound 1 is a competitive inhibitor of human lysosomal beta-hexosaminidase A with K(i) values of 18 microM (beta-subunit) and 220 microM (alpha-subunit). Similar properties were found for the already known 2-acetamido-2-deoxy-D-gluco-hydroximo-1,4-lactone.

摘要

描述了从2-乙酰氨基-2-脱氧-D-葡萄糖出发通过两种不同途径合成2-乙酰氨基-1,4-亚氨基-1,2,4-三脱氧-D-半乳糖醇（1；2-乙酰氨基-4-氨基-1,4-脱水-2,4-二脱氧-D-半乳糖醇）的方法。化合物1是人类溶酶体β-己糖胺酶A的竞争性抑制剂，其对β亚基的抑制常数（Ki）值为18微摩尔，对α亚基的抑制常数（Ki）值为220微摩尔。对于已知的2-乙酰氨基-2-脱氧-D-葡糖-肟基-1,4-内酯也发现了类似的性质。

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