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Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes.

ABSTRACT: Asymmetric aldol addition of simple aldehydes and ketones to electrophiles is a cornerstone reaction for the synthesis of unusual sugars and chiral building blocks. We investigated d-fructose-6-phosphate aldolase from E. coli (FSA) D6X variants as catalysts for the aldol additions of ethanal and nonfunctionalized linear and cyclic aliphatic ketones as nucleophiles to nonphosphorylated hydroxyaldehydes. Thus, addition of propanone, cyclobutanone, cyclopentanone, or ethanal to 3-hydroxypropanal or (S)- or (R)-3-hydroxybutanal catalyzed by FSA D6H and D6Q variants furnished rare deoxysugars in 8-77% isolated yields with high stereoselectivity (97:3 dr and >95% ee).

SUBMITTER: Roldan R

PROVIDER: S-EPMC6135579 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes.

Roldán Raquel R Hernandez Karel K Joglar Jesús J Bujons Jordi J Parella Teodor T Sánchez-Moreno Israel I Hélaine Virgil V Lemaire Marielle M Guérard-Hélaine Christine C Fessner Wolf-Dieter WD Clapés Pere P

ACS catalysis 20180808 9

Asymmetric aldol addition of simple aldehydes and ketones to electrophiles is a cornerstone reaction for the synthesis of unusual sugars and chiral building blocks. We investigated d-fructose-6-phosphate aldolase from <i>E. coli</i> (FSA) D6X variants as catalysts for the aldol additions of ethanal and nonfunctionalized linear and cyclic aliphatic ketones as nucleophiles to nonphosphorylated hydroxyaldehydes. Thus, addition of propanone, cyclobutanone, cyclopentanone, or ethanal to 3-hydroxyprop ...[more]

PMID: 30221031

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