Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes | Zendy

Raquel Roldán | Zendy; Karel Hernández | Zendy; Jesús Joglar | Zendy; Jordi Bujons | Zendy; Teodor Parella | Zendy; Israel SánchezMoreno | Zendy; Virgil Hélaine | Zendy; Marielle Lemaire | Zendy; Christine GuérardHélaine | Zendy; WolfDieter Fessner | Zendy; Pere Clapés | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

Author(s) -

Raquel Roldán,

Karel Hernández,

Jesús Joglar,

Jordi Bujons,

Teodor Parella,

Israel SánchezMoreno,

Virgil Hélaine,

Marielle Lemaire,

Christine GuérardHélaine,

WolfDieter Fessner,

Pere Clapés

Publication year - 2018

Publication title -

acs catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 4.898

H-Index - 198

ISSN - 2155-5435

DOI - 10.1021/acscatal.8b02486

Subject(s) - aldol reaction , nucleophile , simple (philosophy) , chemistry , organic chemistry , catalysis , philosophy , epistemology

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 ).

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research