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...
Autores principales: | , , , , , |
---|---|
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 |