Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

Raquel Roldán; Karel Hernandez; Jesús Joglar; Jordi Bujons; Teodor Parella; Israel Sánchez-Moreno; Virgil Hélaine; Marielle Lemaire; Christine Guérard-Hélaine; Wolf Dieter Fessner; Pere Clapés

doi:10.1021/acscatal.8b02486

Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

Raquel Roldán, Karel Hernandez, Jesús Joglar, Jordi Bujons, Teodor Parella, Israel Sánchez-Moreno, Virgil Hélaine, Marielle Lemaire, Christine Guérard-Hélaine, Wolf Dieter Fessner, Pere Clapés

Nuclear Magnetic Resonance Service

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23 Citations (Scopus)

Abstract

© 2018 American Chemical Society. 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).

Original language	English
Pages (from-to)	8804-8809
Journal	ACS catalysis
Volume	8
DOIs	https://doi.org/10.1021/acscatal.8b02486
Publication status	Published - 7 Sept 2018

Keywords

aldol reaction
aldolases
asymmetric catalysis
biocatalysis
carbon-carbon bond formation
deoxysugars
enzyme engineering

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10.1021/acscatal.8b02486

https://ddd.uab.cat/record/228017

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@article{62f00227513c47fbb1fdd4f5d8490aab,

title = "Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes",

abstract = "{\textcopyright} 2018 American Chemical Society. 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).",

keywords = "aldol reaction, aldolases, asymmetric catalysis, biocatalysis, carbon-carbon bond formation, deoxysugars, enzyme engineering",

author = "Raquel Rold{\'a}n and Karel Hernandez and Jes{\'u}s Joglar and Jordi Bujons and Teodor Parella and Israel S{\'a}nchez-Moreno and Virgil H{\'e}laine and Marielle Lemaire and Christine Gu{\'e}rard-H{\'e}laine and Fessner, {Wolf Dieter} and Pere Clap{\'e}s",

year = "2018",

month = sep,

day = "7",

doi = "10.1021/acscatal.8b02486",

language = "English",

volume = "8",

pages = "8804--8809",

journal = "ACS catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

AU - Roldán, Raquel

AU - Hernandez, Karel

AU - Joglar, Jesús

AU - Bujons, Jordi

AU - Parella, Teodor

AU - Sánchez-Moreno, Israel

AU - Hélaine, Virgil

AU - Lemaire, Marielle

AU - Guérard-Hélaine, Christine

AU - Fessner, Wolf Dieter

AU - Clapés, Pere

PY - 2018/9/7

Y1 - 2018/9/7

N2 - © 2018 American Chemical Society. 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).

AB - © 2018 American Chemical Society. 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).

KW - aldol reaction

KW - aldolases

KW - asymmetric catalysis

KW - biocatalysis

KW - carbon-carbon bond formation

KW - deoxysugars

KW - enzyme engineering

U2 - 10.1021/acscatal.8b02486

DO - 10.1021/acscatal.8b02486

M3 - Article

C2 - 30221031

SN - 2155-5435

VL - 8

SP - 8804

EP - 8809

JO - ACS catalysis

JF - ACS catalysis

ER -

Biocatalytic Aldol Addition of Simple Aliphatic Nucleophiles to Hydroxyaldehydes

Abstract

Keywords

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