Influence of N-amino protecting group on aldolase-catalyzed aldol additions of dihydroxyacetone phosphate to amino aldehydes

Jordi Calveras, Jordi Bujons, Teodor Parella, Ramon Crehuet, Laia Espelt, Jesús Joglar, Pere Clapés

    Research output: Contribution to journalArticleResearchpeer-review

    22 Citations (Scopus)

    Abstract

    This work examines the influence of N-protecting groups on the conversion and stereoselectivity of dihydroxyacetone phosphate (DHAP) dependent aldolase-catalyzed aldol additions of DHAP to N-protected-3-aminopropanal. Phenylacetyl-(PhAc-), tert-butyloxycarbonyl- (tBoc-) and fluoren-9-ylmethoxycarbonyl- (Fmoc-)-3-aminopropanal were evaluated as substrates for d-fructose 1,6-bisphosphate aldolase from rabbit muscle (RAMA), and l-rhamnulose-1-phosphate aldolase (RhuA) and l-fuculose-1-phosphate aldolase (FucA), both from Escherichia coli. Using PhAc and tBoc ca. 70% conversions to the aldol adduct were achieved, whereas Fmoc gave maximum conversions of ca. 25%. The stereoselectivity of the DHAP-aldolases did not depend on the N-protected-3-aminopropanal derivative. Moreover, inversion of FucA stereoselectivity relative to that obtained with the natural l-lactaldehyde was observed. Both N-PhAc and tBoc adduct product derivatives were successfully deprotected by penicillin G acylase (PGA)-catalyzed hydrolysis at pH 7 and by treatment with aqueous TFA (6% v/v), respectively. However, the corresponding cyclic imine sugars could not be isolated, presumable due to the presence of a highly reactive primary amine and a keto group in the molecule, which lead to a number of unexpected reactions. © 2005 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)2648-2656
    JournalTetrahedron
    Volume62
    Issue number11
    DOIs
    Publication statusPublished - 13 Mar 2006

    Keywords

    • Aldol additions
    • Boc group
    • DHAP dependent aldolases
    • Fmoc group
    • Penicillin amidase
    • PhAc group

    Fingerprint

    Dive into the research topics of 'Influence of N-amino protecting group on aldolase-catalyzed aldol additions of dihydroxyacetone phosphate to amino aldehydes'. Together they form a unique fingerprint.

    Cite this