From amino alcohol to aminopolyol: One-pot multienzyme oxidation and aldol addition

Milja Pešić, Carmen López, Josep López-Santín, Gregorio Álvaro

Research output: Contribution to journalArticleResearchpeer-review

13 Citations (Scopus)

Abstract

In this work, the successful coupling of enzymatic oxidation and aldol addition reactions for the synthesis of a Cbz-aminopolyol from a Cbz-amino alcohol was achieved for the first time in a multienzymatic one-pot system. The two-step cascade reaction consisted of the oxidation of Cbz-ethanolamine to Cbz-glycinal catalyzed by chloroperoxidase from the fungus Caldariomyces fumago and aldol addition of dihydroxyacetone phosphate to Cbz-glycinal catalyzed by rhamnulose-1-phosphate aldolase expressed as a recombinant enzyme in Escherichia coli, yielding (3R,4S)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1-O- phosphonopent-2-ulose. Tools of enzymatic immobilization, reactor configurations, and modification of the reaction medium were applied to highly increase the production of the target compound. While the use of soluble enzymes yielded only 23.6 % of Cbz-aminopolyol due to rapid enzyme inactivation, the use of immobilized ones permitted an almost complete consumption of Cbz-ethanolamine, reaching Cbz-aminopolyol yields of 69.1 and 71.9 % in the stirred-tank and packed-bed reactor, respectively. Furthermore, the reaction production was 18-fold improved when it was catalyzed by immobilized enzymes in the presence of 5 % (v/v) dioxane, reaching a value of 86.6 mM of Cbz-aminopoliol (31 g/L). © 2013 Springer-Verlag Berlin Heidelberg.
Original languageEnglish
Pages (from-to)7173-7183
JournalApplied Microbiology and Biotechnology
Volume97
DOIs
Publication statusPublished - 1 Aug 2013

Keywords

  • Aminopolyol synthesis
  • Enzymatic immobilization
  • Enzymatic reactor configuration
  • One-pot multienzymatic reaction

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