Cargando…

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3‐hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantio...

Descripción completa

Detalles Bibliográficos
Autores principales: Mareya, Tatenda M., Coady, Tracey M., O'Reilly, Catherine, Kinsella, Michael, Coffey, Lee, Lennon, Claire M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7184877/
https://www.ncbi.nlm.nih.gov/pubmed/32346499
http://dx.doi.org/10.1002/open.202000088
_version_ 1783526664354922496
author Mareya, Tatenda M.
Coady, Tracey M.
O'Reilly, Catherine
Kinsella, Michael
Coffey, Lee
Lennon, Claire M.
author_facet Mareya, Tatenda M.
Coady, Tracey M.
O'Reilly, Catherine
Kinsella, Michael
Coffey, Lee
Lennon, Claire M.
author_sort Mareya, Tatenda M.
collection PubMed
description A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3‐hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo‐aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β‐aminonitriles, structural analogues of β‐hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α‐ aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.
format Online
Article
Text
id pubmed-7184877
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-71848772020-04-28 Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium Mareya, Tatenda M. Coady, Tracey M. O'Reilly, Catherine Kinsella, Michael Coffey, Lee Lennon, Claire M. ChemistryOpen Full Papers A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3‐hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo‐aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β‐aminonitriles, structural analogues of β‐hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α‐ aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation. John Wiley and Sons Inc. 2020-04-27 /pmc/articles/PMC7184877/ /pubmed/32346499 http://dx.doi.org/10.1002/open.202000088 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Mareya, Tatenda M.
Coady, Tracey M.
O'Reilly, Catherine
Kinsella, Michael
Coffey, Lee
Lennon, Claire M.
Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium
title Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium
title_full Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium
title_fullStr Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium
title_full_unstemmed Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium
title_short Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium
title_sort process optimisation studies and aminonitrile substrate evaluation of rhodococcus erythropolis set1, a nitrile hydrolyzing bacterium
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7184877/
https://www.ncbi.nlm.nih.gov/pubmed/32346499
http://dx.doi.org/10.1002/open.202000088
work_keys_str_mv AT mareyatatendam processoptimisationstudiesandaminonitrilesubstrateevaluationofrhodococcuserythropolisset1anitrilehydrolyzingbacterium
AT coadytraceym processoptimisationstudiesandaminonitrilesubstrateevaluationofrhodococcuserythropolisset1anitrilehydrolyzingbacterium
AT oreillycatherine processoptimisationstudiesandaminonitrilesubstrateevaluationofrhodococcuserythropolisset1anitrilehydrolyzingbacterium
AT kinsellamichael processoptimisationstudiesandaminonitrilesubstrateevaluationofrhodococcuserythropolisset1anitrilehydrolyzingbacterium
AT coffeylee processoptimisationstudiesandaminonitrilesubstrateevaluationofrhodococcuserythropolisset1anitrilehydrolyzingbacterium
AT lennonclairem processoptimisationstudiesandaminonitrilesubstrateevaluationofrhodococcuserythropolisset1anitrilehydrolyzingbacterium