弱氧化醋杆菌对支链糖醇的氧化作用：L-树酮糖的立体特异性合成。

Oxidation of a branched-chain alditol by acetobacter suboxydans: a stereospecific synthesis of L-dendroketose.

作者信息

Szarek W A, Schnarr G W, Jarrell H C, Jones J K

出版信息

Carbohydr Res. 1977 Jan;53(1):101-8. doi: 10.1016/s0008-6215(00)85458-0.

Abstract

A synthesis of L-dendroketose (5) has been achieved by microbiological oxidation by Acetobacter suboxydans of the branched-chain alditol 2-C-(hydroxy-methyl)-D-erythro-pentitol (4). Treatment of the oxidation product with acetone, copper(II) sulfate, and sulfuric acid afforded the two di-O-isopropylidene-L-dendro-ketose derivatives 6 and 7. Assignment of configuration at the branching carbon atom (C-4) and at the anomeric center in 6 and 7 was made on the basis of the carbon-13 magnetic resonance spectra of these derivatives.

摘要

通过弱氧化醋杆菌对支链糖醇2-C-(羟甲基)-D-赤藓戊糖醇(4)进行微生物氧化，已实现L-树酮糖(5)的合成。用丙酮、硫酸酮和硫酸处理氧化产物，得到两种二-O-异亚丙基-L-树酮糖衍生物6和7。基于这些衍生物的碳-13磁共振谱，确定了6和7中支链碳原子(C-4)和端基中心的构型。