Asymmetric assembly of aldose carbohydrates from formaldehyde and glycolaldehyde by tandem biocatalytic aldol reactions

Anna Szekrenyi, Xavier Garrabou, Teodor Parella, Jesús Joglar, Jordi Bujons, Pere Clapés

    Research output: Contribution to journalArticleResearchpeer-review

    46 Citations (Scopus)

    Abstract

    © 2015 Macmillan Publishers Limited. All rights reserved. The preparation of multifunctional chiral molecules can be greatly simplified by adopting a route via the sequential catalytic assembly of achiral building blocks. The catalytic aldol assembly of prebiotic compounds into stereodefined pentoses and hexoses is an as yet unmet challenge. Such a process would be of remarkable synthetic utility and highly significant with regard to the origin of life. Pursuing an expedient enzymatic approach, here we use engineered D-fructose-6-phosphate aldolase from Escherichia coli to prepare a series of three- to six-carbon aldoses by sequential one-pot additions of glycolaldehyde. Notably, the pertinent selection of the aldolase variant provides control of the sugar size. The stereochemical outcome of the addition was also altered to allow the synthesis of L-glucose and related derivatives. Such engineered biocatalysts may offer new routes for the straightforward synthesis of natural molecules and their analogues that circumvent the intricate enzymatic pathways forged by evolution.
    Original languageEnglish
    Pages (from-to)724-729
    JournalNature Chemistry
    Volume7
    Issue number9
    DOIs
    Publication statusPublished - 22 Sep 2015

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