skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Catalytic Upgrading in Bacteria-Compatible Conditions via a Biocompatible Aldol Condensation

Abstract

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.

Authors:
 [1];  [1];  [1];  [1];  [1]
  1. Univ. of Colorado, Boulder, CO (United States)
Publication Date:
Research Org.:
Univ. of California, San Diego, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1467610
Grant/Contract Number:  
SC0006398
Resource Type:
Accepted Manuscript
Journal Name:
ACS Sustainable Chemistry & Engineering
Additional Journal Information:
Journal Volume: 4; Journal Issue: 3; Journal ID: ISSN 2168-0485
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; organocatalysis; microbes; green chemistry; 2-ethylhexenal; β-alanine; glycerol tributyrate

Citation Formats

Domaille, Dylan W., Hafenstine, Glenn R., Greer, Mattias A., Goodwin, Andrew P., and Cha, Jennifer N.. Catalytic Upgrading in Bacteria-Compatible Conditions via a Biocompatible Aldol Condensation. United States: N. p., 2016. Web. doi:10.1021/acssuschemeng.5b01590.
Domaille, Dylan W., Hafenstine, Glenn R., Greer, Mattias A., Goodwin, Andrew P., & Cha, Jennifer N.. Catalytic Upgrading in Bacteria-Compatible Conditions via a Biocompatible Aldol Condensation. United States. doi:10.1021/acssuschemeng.5b01590.
Domaille, Dylan W., Hafenstine, Glenn R., Greer, Mattias A., Goodwin, Andrew P., and Cha, Jennifer N.. Mon . "Catalytic Upgrading in Bacteria-Compatible Conditions via a Biocompatible Aldol Condensation". United States. doi:10.1021/acssuschemeng.5b01590. https://www.osti.gov/servlets/purl/1467610.
@article{osti_1467610,
title = {Catalytic Upgrading in Bacteria-Compatible Conditions via a Biocompatible Aldol Condensation},
author = {Domaille, Dylan W. and Hafenstine, Glenn R. and Greer, Mattias A. and Goodwin, Andrew P. and Cha, Jennifer N.},
abstractNote = {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.},
doi = {10.1021/acssuschemeng.5b01590},
journal = {ACS Sustainable Chemistry & Engineering},
number = 3,
volume = 4,
place = {United States},
year = {2016},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 9 works
Citation information provided by
Web of Science

Save / Share: