Chemoenzymatic Deracemization of Secondary Alcohols by using a TEMPO-Iodine-Alcohol Dehydrogenase System
(2015) In ChemCatChem 7(24). p.4016-4020- Abstract
- A deracemization system for secondary alcohols was established after the analysis of individual steps and their compatibility in one pot. The chemical oxidation and bioreduction occurred in a sequential manner to yield 1-arylethanols and lineal aliphatic alcohols with excellent conversions and enantiomeric excess values. The oxidation step was performed by using 2,2,6,6-tetramethylpiperidin-1-oxyl and iodine. This chemical process was extremely favored by sonication, which allowed quantitative formation of the corresponding ketone intermediates after just 1h. Simple destruction of iodine in the same pot allowed sequential bioreduction of the ketones by using either Prelog or antiPrelog enzymes, which led to the preparation of the... (More)
- A deracemization system for secondary alcohols was established after the analysis of individual steps and their compatibility in one pot. The chemical oxidation and bioreduction occurred in a sequential manner to yield 1-arylethanols and lineal aliphatic alcohols with excellent conversions and enantiomeric excess values. The oxidation step was performed by using 2,2,6,6-tetramethylpiperidin-1-oxyl and iodine. This chemical process was extremely favored by sonication, which allowed quantitative formation of the corresponding ketone intermediates after just 1h. Simple destruction of iodine in the same pot allowed sequential bioreduction of the ketones by using either Prelog or antiPrelog enzymes, which led to the preparation of the enantiopure alcohols in excellent yields. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/8542837
- author
- Mendez-Sanchez, Daniel ; Mangas, Juan LU ; Lavandera, Ivan ; Gotor, Vicente and Gotor-Fernandez, Vicente
- organization
- publishing date
- 2015
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- alcohols, biocatalysis, deracemization, oxidoreductases, TEMPO
- in
- ChemCatChem
- volume
- 7
- issue
- 24
- pages
- 4016 - 4020
- publisher
- John Wiley & Sons Inc.
- external identifiers
-
- wos:000366838200003
- scopus:84950311274
- ISSN
- 1867-3880
- DOI
- 10.1002/cctc.201500816
- language
- English
- LU publication?
- yes
- id
- c3e5b5af-0f05-43bb-828d-eaa6826cf876 (old id 8542837)
- date added to LUP
- 2016-04-01 09:48:22
- date last changed
- 2022-04-19 19:45:50
@article{c3e5b5af-0f05-43bb-828d-eaa6826cf876,
abstract = {{A deracemization system for secondary alcohols was established after the analysis of individual steps and their compatibility in one pot. The chemical oxidation and bioreduction occurred in a sequential manner to yield 1-arylethanols and lineal aliphatic alcohols with excellent conversions and enantiomeric excess values. The oxidation step was performed by using 2,2,6,6-tetramethylpiperidin-1-oxyl and iodine. This chemical process was extremely favored by sonication, which allowed quantitative formation of the corresponding ketone intermediates after just 1h. Simple destruction of iodine in the same pot allowed sequential bioreduction of the ketones by using either Prelog or antiPrelog enzymes, which led to the preparation of the enantiopure alcohols in excellent yields.}},
author = {{Mendez-Sanchez, Daniel and Mangas, Juan and Lavandera, Ivan and Gotor, Vicente and Gotor-Fernandez, Vicente}},
issn = {{1867-3880}},
keywords = {{alcohols; biocatalysis; deracemization; oxidoreductases; TEMPO}},
language = {{eng}},
number = {{24}},
pages = {{4016--4020}},
publisher = {{John Wiley & Sons Inc.}},
series = {{ChemCatChem}},
title = {{Chemoenzymatic Deracemization of Secondary Alcohols by using a TEMPO-Iodine-Alcohol Dehydrogenase System}},
url = {{http://dx.doi.org/10.1002/cctc.201500816}},
doi = {{10.1002/cctc.201500816}},
volume = {{7}},
year = {{2015}},
}