Open AccessCatalytic Upgrading in Bacteria-Compatible Conditions via a Biocompatible Aldol Condensation
Author(s) -
Dylan W. Domaille,
Glenn R. Hafenstine,
Mattias A. Greer,
Andrew P. Goodwin,
N. Jennifer
Publication year - 2016
Publication title -
acs sustainable chemistry and engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.878
H-Index - 109
ISSN - 2168-0485
DOI - 10.1021/acssuschemeng.5b01590
Subject(s) - biocompatible material , aldol condensation , catalysis , chemistry , aldol reaction , bacteria , organic chemistry , condensation , chemical engineering , biochemical engineering , combinatorial chemistry , biology , medicine , biomedical engineering , genetics , engineering , physics , thermodynamics
Integrating non-enzymatic chemistry with living systems has the potential to greatly expand the types and yields of chemicals that can be sourced from renewable feedstocks. The in situ conversion of microbial metabolites to higher order products will ensure their continuous generation starting from a given cellular reaction mixture. We present here a systematic study of different organocatalysts that enable aldol condensation in biological media under physiological conditions of neutral pH, moderate temperature, and ambient pressure. The relative toxicities of each catalyst were tested against bacteria, and the catalysts were found to provide good yields of homoaldol products in bacterial cultures containing aldehydes. Lastly, we demonstrate that a biocompatible oil can be used to selectively extract the upgraded products, which enabes facile isolation and decreases the product toxicity to microbes.