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Biosynthesis of ethyl caproate and other short ethyl esters catalyzed by cutinase in organic solvent

Authorized Users Only
2009
Authors
de Barros, Dragana P. C.
Fonseca, Luis P.
Fernandes, P.
Cabral, Joaquim M. S.
Mojović, Ljiljana
Article (Published version)
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Abstract
The main objective of this work was to study the enzymatic synthesis of short chain ethyl esters, a group of relevant aroma molecules, by Fusarium solani pisi cutinase in an organic solvent media (iso-octane), and to assess the influence of different parameters on the reaction yield. Cutinase displayed high initial esterification rates in iso-octane. which amounted to 1.15 mu mol min(-1) mg(-1) for ethyl butyrate (C-4 acid chain) and 1.06 mu mol min(-1) mg(-1) for ethyl valerate (C-S acid chain). High product yields, 84% for ethyl butyrate and 96% for ethyl valerate, were observed after 6 h of reaction, for an initial equimolar concentration of substrates (0.1 M). The highest product yield (97%) was observed for ethyl caproate (C-6) synthesis, a compound which is a part of natural apple and pineapple flavour, for an alcohol:acid molar ratio of 2 (0.2 M ethanol concentration). Cutinase affinity for short chain length carboxylic acids (C-4-C-6) in ester synthesis in iso-octane confirmed ...previous observations in reversed micellar system.

Keywords:
Ethyl caproate / Short chain ethyl esters / Cutinase / Organic solvent / Iso-octane
Source:
Journal of Molecular Catalysis B-Enzymatic, 2009, 60, 3-4, 178-185
Publisher:
  • Elsevier Science Bv, Amsterdam
Funding / projects:
  • Fundacao para a Ciencia e a Tecnologia (Portugal)Portuguese Foundation for Science and Technology [SFRH/BD/24703/2005]

DOI: 10.1016/j.molcatb.2009.05.004

ISSN: 1381-1177

WoS: 000269466600013

Scopus: 2-s2.0-68149151029
[ Google Scholar ]
39
37
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1423
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - de Barros, Dragana P. C.
AU  - Fonseca, Luis P.
AU  - Fernandes, P.
AU  - Cabral, Joaquim M. S.
AU  - Mojović, Ljiljana
PY  - 2009
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1423
AB  - The main objective of this work was to study the enzymatic synthesis of short chain ethyl esters, a group of relevant aroma molecules, by Fusarium solani pisi cutinase in an organic solvent media (iso-octane), and to assess the influence of different parameters on the reaction yield. Cutinase displayed high initial esterification rates in iso-octane. which amounted to 1.15 mu mol min(-1) mg(-1) for ethyl butyrate (C-4 acid chain) and 1.06 mu mol min(-1) mg(-1) for ethyl valerate (C-S acid chain). High product yields, 84% for ethyl butyrate and 96% for ethyl valerate, were observed after 6 h of reaction, for an initial equimolar concentration of substrates (0.1 M). The highest product yield (97%) was observed for ethyl caproate (C-6) synthesis, a compound which is a part of natural apple and pineapple flavour, for an alcohol:acid molar ratio of 2 (0.2 M ethanol concentration). Cutinase affinity for short chain length carboxylic acids (C-4-C-6) in ester synthesis in iso-octane confirmed previous observations in reversed micellar system.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Catalysis B-Enzymatic
T1  - Biosynthesis of ethyl caproate and other short ethyl esters catalyzed by cutinase in organic solvent
EP  - 185
IS  - 3-4
SP  - 178
VL  - 60
DO  - 10.1016/j.molcatb.2009.05.004
ER  - 
@article{
author = "de Barros, Dragana P. C. and Fonseca, Luis P. and Fernandes, P. and Cabral, Joaquim M. S. and Mojović, Ljiljana",
year = "2009",
abstract = "The main objective of this work was to study the enzymatic synthesis of short chain ethyl esters, a group of relevant aroma molecules, by Fusarium solani pisi cutinase in an organic solvent media (iso-octane), and to assess the influence of different parameters on the reaction yield. Cutinase displayed high initial esterification rates in iso-octane. which amounted to 1.15 mu mol min(-1) mg(-1) for ethyl butyrate (C-4 acid chain) and 1.06 mu mol min(-1) mg(-1) for ethyl valerate (C-S acid chain). High product yields, 84% for ethyl butyrate and 96% for ethyl valerate, were observed after 6 h of reaction, for an initial equimolar concentration of substrates (0.1 M). The highest product yield (97%) was observed for ethyl caproate (C-6) synthesis, a compound which is a part of natural apple and pineapple flavour, for an alcohol:acid molar ratio of 2 (0.2 M ethanol concentration). Cutinase affinity for short chain length carboxylic acids (C-4-C-6) in ester synthesis in iso-octane confirmed previous observations in reversed micellar system.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Catalysis B-Enzymatic",
title = "Biosynthesis of ethyl caproate and other short ethyl esters catalyzed by cutinase in organic solvent",
pages = "185-178",
number = "3-4",
volume = "60",
doi = "10.1016/j.molcatb.2009.05.004"
}
de Barros, D. P. C., Fonseca, L. P., Fernandes, P., Cabral, J. M. S.,& Mojović, L.. (2009). Biosynthesis of ethyl caproate and other short ethyl esters catalyzed by cutinase in organic solvent. in Journal of Molecular Catalysis B-Enzymatic
Elsevier Science Bv, Amsterdam., 60(3-4), 178-185.
https://doi.org/10.1016/j.molcatb.2009.05.004
de Barros DPC, Fonseca LP, Fernandes P, Cabral JMS, Mojović L. Biosynthesis of ethyl caproate and other short ethyl esters catalyzed by cutinase in organic solvent. in Journal of Molecular Catalysis B-Enzymatic. 2009;60(3-4):178-185.
doi:10.1016/j.molcatb.2009.05.004 .
de Barros, Dragana P. C., Fonseca, Luis P., Fernandes, P., Cabral, Joaquim M. S., Mojović, Ljiljana, "Biosynthesis of ethyl caproate and other short ethyl esters catalyzed by cutinase in organic solvent" in Journal of Molecular Catalysis B-Enzymatic, 60, no. 3-4 (2009):178-185,
https://doi.org/10.1016/j.molcatb.2009.05.004 . .

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