NDLI: Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Content Provider	Springer Nature Link
Author	Świzdor, Alina Janeczko, Tomasz Dmochowska Gładysz, Jadwiga
Copyright Year	2010
Abstract	Didymosphaeriaigniaria is a promising biocatalyst in asymmetric reductions of prochiral aromatic-aliphatic ketones such as acetonaphthones, acetophenones, and acetylpyridines. The organism converted the substrates mainly to (S)-alcohols. Excellent results in terms of conversion and enantioselectivity (100% yield, >99% ee) were obtained with acetonaphthones. In case of acetyl pyridines, the optical purity of the product depended on the position of the carbonyl group on the pyridine ring and followed the order 2-acetyl ≫ 4-acetyl > 3-acetyl-pyridine. Transformation of o-methoxy-acetophenone gave optically pure (S)-(-)-1-(2-methoxyphenyl)-ethanol in 95% yield. The transformation of para-methyl ketone gave (R)-alcohol (81% ee), whereas para-bromo ketone gave (S)-alcohol (98% ee). Monitoring of the biotransformation of these substrates over time led to the conclusion that for both substrates, non-selective carbonyl group reduction occurred in the first step, followed by selective oxidation of the (R)-isomer of p-bromo-phenylethanol and selective oxidation of the (S)-isomer of p-methyl-phenylethanol. D. igniaria exhibited poor enantioselectivity in the reduction of bicyclic aryl-aliphatic ketones such as 1- and 2-tetralones. Only (S)-5-methoxy-1-tetralol was obtained in optically pure (>99% ee) form.
Starting Page	1121
Ending Page	1130
Page Count	10
File Format	PDF
ISSN	13675435
Journal	Journal of Industrial Microbiology and Biotechnology
Volume Number	37
Issue Number	11
e-ISSN	14765535
Language	English
Publisher	Springer-Verlag
Publisher Date	2010-06-11
Publisher Place	Berlin, Heidelberg
Access Restriction	Subscribed
Subject Keyword	Asymmetric bioreduction Chiral alcohol Enantioselectivity Didymosphaeria igniaria Microbiology Bioinformatics Biotechnology Genetic Engineering Inorganic Chemistry Biochemistry
Content Type	Text
Resource Type	Article
Subject	Medicine Bioengineering Applied Microbiology and Biotechnology Biotechnology

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Production of chiral alcohols from prochiral ketones by microalgal photo-biocatalytic asymmetric reduction reaction

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Chemoenzymatic resolution of racemic Wieland–Miescher and Hajos–Parrish ketones

Burkholderia cenocepacia: a new biocatalyst for efficient bioreduction of ezetimibe intermediate

Towards the discovery of alcohol dehydrogenases: NAD(P)H fluorescence-based screening and characterization of the newly isolated Rhodococcus erythropolis WZ010 in the preparation of chiral aryl secondary alcohols

Photobiocatalyzed asymmetric reduction of ketones using Chlorella sp. MK201

Synthesis of methyl ketones by metabolically engineered Escherichia coli

Biocatalytic deracemisation of aliphatic β-hydroxy esters: Improving the enantioselectivity by optimisation of reaction parameters

A new generation

Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Similar Documents

Production of chiral alcohols from prochiral ketones by microalgal photo-biocatalytic asymmetric reduction reaction

Asymmetric reduction of prochiral ketones to chiral alcohols catalyzed by plants tissue

Chemoenzymatic resolution of racemic Wieland–Miescher and Hajos–Parrish ketones

Burkholderia cenocepacia: a new biocatalyst for efficient bioreduction of ezetimibe intermediate

Towards the discovery of alcohol dehydrogenases: NAD(P)H fluorescence-based screening and characterization of the newly isolated Rhodococcus erythropolis WZ010 in the preparation of chiral aryl secondary alcohols

Photobiocatalyzed asymmetric reduction of ketones using Chlorella sp. MK201

Synthesis of methyl ketones by metabolically engineered Escherichia coli

Biocatalytic deracemisation of aliphatic β-hydroxy esters: Improving the enantioselectivity by optimisation of reaction parameters

A new generation

Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones