Expedient synthesis of C-aryl carbohydrates by consecutive biocatalytic benzoin and aldol reactions

Karel Hernández, Teodor Parella, Jesffls Joglar, Jordi Bujons, Martina Pohl, Pere Clapés

    Research output: Contribution to journalArticleResearchpeer-review

    11 Citations (Scopus)

    Abstract

    © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. The introduction of aromatic residues connected by a C-C bond into the non-reducing end of carbohydrates is highly significant for the development of innovative structures with improved binding affinity and selectivity (e.g., C-aril-sLex). In this work, an expedient asymmetric "de novo" synthetic route to new aryl carbohydrate derivatives based on two sequential stereoselectively biocatalytic carboligation reactions is presented. First, the benzoin reaction of aromatic aldehydes to dimethoxyacetaldehyde is conducted, catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I. Then, the a-hydroxyketones formed are reduced by using NaBH4 yielding the anti diol. After acetal hydrolysis, the aldol addition of dihydroxyacetone, hydroxyacetone, or glycolaldehyde catalyzed by the stereocomplementary d-fructose-6-phosphate aldolase and l-rhamnulose-1-phosphate aldolase is performed. Both aldolases accept unphosphorylated donor substrates, avoiding the need of handling the phosphate group that the dihydroxyacetone phosphatedependent aldolases require. In this way, 6-C-aryl-l -sorbose, 6-C-aryl-l-fructose, 6-C-aryl- l-tagatose, and 5-C-aryl-l-xylose derivatives are prepared by using this methodology.
    Original languageEnglish
    Pages (from-to)3335-3346
    JournalChemistry - A European Journal
    Volume21
    Issue number8
    DOIs
    Publication statusPublished - 16 Feb 2015

    Keywords

    • Aldolases
    • Benzaldehyde lyase
    • C-C bond formation
    • Carbohydrates
    • Enzyme catalysis

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