Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

Overview

Journal ACS Catal

Publisher American Chemical Society

Date 2018 Sep 18

PMID 30221031

Citations 5

Authors

Raquel Roldan

Karel Hernandez

Jesus Joglar

Jordi Bujons

Teodor Parella

Israel Sanchez-Moreno

Virgil Helaine

Marielle Lemaire

Christine Guerard-Helaine

Wolf-Dieter Fessner

Pere Clapes

Affiliations

Soon will be listed here.

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 (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 ()- or ()-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% ).

Citing Articles

Biocatalytic Transamination of Aldolase-Derived 3-Hydroxy Ketones.

Pickl M, Ebner M, Gittings S, Clapes P, Kroutil W Adv Synth Catal. 2024; 365(9):1485-1495.

PMID: 38516568 PMC: 10952931. DOI: 10.1002/adsc.202300201.

Synthesis of a precursor of D-fagomine by immobilized fructose-6-phosphate aldolase.

Masdeu G, Vazquez L, Lopez-Santin J, Caminal G, Kralj S, Makovec D PLoS One. 2021; 16(4):e0250513.

PMID: 33886681 PMC: 8062046. DOI: 10.1371/journal.pone.0250513.

Streptavidin-Hosted Organocatalytic Aldol Addition.

Santi N, Morrill L, Luk L Molecules. 2020; 25(10).

PMID: 32466220 PMC: 7287710. DOI: 10.3390/molecules25102457.

Enantioselective Aldol Addition of Acetaldehyde to Aromatic Aldehydes Catalyzed by Proline-Based Carboligases.

Saifuddin M, Guo C, Biewenga L, Saravanan T, Charnock S, Poelarends G ACS Catal. 2020; 10(4):2522-2527.

PMID: 32117575 PMC: 7045556. DOI: 10.1021/acscatal.0c00039.

Aldolase-Catalyzed Asymmetric Synthesis of N-Heterocycles by Addition of Simple Aliphatic Nucleophiles to Aminoaldehydes.

Roldan R, Hernandez K, Joglar J, Bujons J, Parella T, Fessner W Adv Synth Catal. 2019; 361(11):2673-2687.

PMID: 31680790 PMC: 6813633. DOI: 10.1002/adsc.201801530.

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