Issue 85, 2015

A new concept for production of (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose, a precursor of d-fagomine

Abstract

A novel cascade reaction for the production of aldol adduct (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose was studied in this work. The strategy combines three enzymes in one pot: (i) horse liver alcohol dehydrogenase for the oxidation of N-Cbz-3-aminopropanol to the corresponding aldehyde, (ii) NADH oxidase for the regeneration of coenzyme NAD+ and (iii) D-fructose-6-phosphate aldolase from E. coli A129S variant for the aldol addition of dihydroxyacetone to N-Cbz-3-aminopropanal. On the basis of preliminary experiments, optimization of the initial reaction conditions was done using statistical methods, i.e. factorial design of experiments. 79% yield of aldol adduct was achieved in the batch reactor after optimization.

Graphical abstract: A new concept for production of (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose, a precursor of d-fagomine

Supplementary files

Article information

Article type
Paper
Submitted
21 Jul 2015
Accepted
11 Aug 2015
First published
11 Aug 2015
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2015,5, 69819-69828

Author version available

A new concept for production of (3S,4R)-6-[(benzyloxycarbonyl)amino]-5,6-dideoxyhex-2-ulose, a precursor of D-fagomine

M. Sudar, Z. Findrik, Đ. Vasić-Rački, A. Soler and P. Clapés, RSC Adv., 2015, 5, 69819 DOI: 10.1039/C5RA14414K

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