α-L-艾杜糖苷酸酶抑制剂L-艾杜糖-1,4-内酯的合成

Synthesis of L-idaro-1,4-lactone, an inhibitor of alpha-L-idosiduronase.

作者信息

Herd J K, Mayberry W R, Snell R L

出版信息

Carbohydr Res. 1982 Jan 1;99(1):33-9. doi: 10.1016/s0008-6215(00)80972-6.

Abstract

L-idaro-1,4-lactone was synthesized by two different, published methods: (1) epimerization of monopotassium D-glucarate by refluxing in aqueous barium hydroxide, and (2) oxidation of L-iditol by heating in dilute nitric acid. The lactone, formed by heat dehydration from aqueous solution at low pH, was purified by paper chromatography, and quantitated by gas-liquid chromatography using inositol as the internal standard. The monolactone inhibited human, seminal-fluid alpha-L-idosiduronase activity, with either phenyl or 4-methylumbelliferyl alpha-L-idosiduronic acid as the substrate, to the same degree as D-glucaro-1,4-lactone inhibits alpha-D-glucosiduronase.

摘要

L-艾杜糖-1,4-内酯通过两种不同的已发表方法合成：（1）在氢氧化钡水溶液中回流使D-葡萄糖酸钾差向异构化，以及（2）在稀硝酸中加热使L-艾杜糖醇氧化。由低pH值水溶液经热脱水形成的内酯通过纸色谱法纯化，并以肌醇作为内标通过气液色谱法定量。该单内酯以苯基或4-甲基伞形基α-L-艾杜糖醛酸作为底物时，抑制人精液α-L-艾杜糖苷酸酶活性的程度与D-葡萄糖醛酸-1,4-内酯抑制α-D-葡萄糖醛酸酶的程度相同。