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Title: Membrane Permeability of Fatty Acyl Compounds Studied via Molecular Simulation

Abstract

Interest in fatty acid-derived products as fuel and chemical precursors has grown substantially. Microbes can be genetically engineered to produce fatty acid-derived products that are able to cross host membranes and can be extracted into an applied organic overlay. This process is thought to be passive, with a rate dependent on the chemistry of the crossing compound. The relationship between the chemical composition and the energetics and kinetics of product accumulation within the overlay is not well understood. Through biased and unbiased molecular simulation, we compute the membrane permeability coefficients from production to extraction for different fatty acyl products, including fatty acids, fatty alcohols, fatty aldehydes, alkanes, and alkenes. These simulations identify specific interactions that accelerate the transit of aldehydes across the membrane bilayer relative to other oxidized products, specifically the lack of hydrogen bonds to the surrounding membrane environment. However, since extraction from the outer membrane leaflet into the organic phase is found to be rate limiting for the entire process, we find that fatty alcohols and fatty aldehydes would both manifest similar fluxes into a dodecane overlay under equivalent conditions, outpacing the accumulation of acids or alkanes into the organic phase. Since aldehydes are known to be highlymore » reactive as well as toxic in high quantities, the findings suggest that indeed fatty alcohols are the optimal long-tail fatty acyl product for extraction.« less

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
+ Show Author Affiliations
  1. National Renewable Energy Lab. (NREL), Golden, CO (United States)
Publication Date:
Research Org.:
National Renewable Energy Laboratory (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), NREL Laboratory Directed Research and Development (LDRD)
OSTI Identifier:
1415127
Report Number(s):
NREL/JA-2700-69128
Journal ID: ISSN 1520-6106; TRN: US1800758
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry
Additional Journal Information:
Journal Volume: 121; Journal Issue: 50; Journal ID: ISSN 1520-6106
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; biochemistry; precursors; permeability

Citation Formats

Vermaas, Josh V., Beckham, Gregg T., and Crowley, Michael F.. Membrane Permeability of Fatty Acyl Compounds Studied via Molecular Simulation. United States: N. p., 2017. Web. doi:10.1021/acs.jpcb.7b08233.
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Vermaas, Josh V., Beckham, Gregg T., & Crowley, Michael F.. Membrane Permeability of Fatty Acyl Compounds Studied via Molecular Simulation. United States. https://doi.org/10.1021/acs.jpcb.7b08233
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Vermaas, Josh V., Beckham, Gregg T., and Crowley, Michael F.. Tue . "Membrane Permeability of Fatty Acyl Compounds Studied via Molecular Simulation". United States. https://doi.org/10.1021/acs.jpcb.7b08233. https://www.osti.gov/servlets/purl/1415127.
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@article{osti_1415127,
title = {Membrane Permeability of Fatty Acyl Compounds Studied via Molecular Simulation},
author = {Vermaas, Josh V. and Beckham, Gregg T. and Crowley, Michael F.},
abstractNote = {Interest in fatty acid-derived products as fuel and chemical precursors has grown substantially. Microbes can be genetically engineered to produce fatty acid-derived products that are able to cross host membranes and can be extracted into an applied organic overlay. This process is thought to be passive, with a rate dependent on the chemistry of the crossing compound. The relationship between the chemical composition and the energetics and kinetics of product accumulation within the overlay is not well understood. Through biased and unbiased molecular simulation, we compute the membrane permeability coefficients from production to extraction for different fatty acyl products, including fatty acids, fatty alcohols, fatty aldehydes, alkanes, and alkenes. These simulations identify specific interactions that accelerate the transit of aldehydes across the membrane bilayer relative to other oxidized products, specifically the lack of hydrogen bonds to the surrounding membrane environment. However, since extraction from the outer membrane leaflet into the organic phase is found to be rate limiting for the entire process, we find that fatty alcohols and fatty aldehydes would both manifest similar fluxes into a dodecane overlay under equivalent conditions, outpacing the accumulation of acids or alkanes into the organic phase. Since aldehydes are known to be highly reactive as well as toxic in high quantities, the findings suggest that indeed fatty alcohols are the optimal long-tail fatty acyl product for extraction.},
doi = {10.1021/acs.jpcb.7b08233},
journal = {Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry},
number = 50,
volume = 121,
place = {United States},
year = {2017},
month = {10}
}
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https://doi.org/10.1021/acs.jpcb.7b08233
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