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

AuthorsSudar, M.; Findrik, Z.; Vasić -Rački, D.; Soler, Anna; Clapés Saborit, Pere
Issue Date2015
CitationRSC Advances 5: 69819- 69828 (2015)
Abstract© The Royal Society of Chemistry 2015. 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<sup>+</sup> 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.
Publisher version (URL)http://dx.doi.org/10.1039/c5ra14414k
Identifiersdoi: 10.1039/c5ra14414k
issn: 2046-2069
Appears in Collections:(IQAC) Artículos
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