A highly enantioselective preparation (92-99% enantiomeric excess, 100% conversion) of various 4-aryl-2-hydroxy but-3-enoic carboxylic acid esters from the corresponding 4-phenyl-2-keto but-3-enoic acid esters mediated by plant cell cultures of Daucus carota under mild and environmentally benign conditions in aqueous medium is described. © 2003 Elsevier B.V. All rights reserved.

Anju Chadha

Department Of Biotechnology

Esters

Isomers

PLANT CELL CULTURE

reduction

stereochemistry

Enantiomers

Stereoselectivity

Catalyst selectivity

butyric acid derivative

carboxylic acid derivative

ester derivative

phenyl group

polycyclic aromatic hydrocarbon derivative

aqueous solution

article

CARROT

controlled study

enantiomer

Enantioselectivity

Environment

nonhuman

plant cell

DAUCUS CAROTA

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Journal of Molecular Catalysis B: Enzymatic

This review highlights the importance of the biocatalyst, Candida parapsilosis for oxidation and reduction reactions of organic compounds and establishes its versatility to generate a variety of chiral synthons. Appropriately designed reactions using C. parapsilosis effect efficient catalysis of organic transformations such as deracemization, enantioselective reduction of prochiral ketones, imines, and kinetic resolution of racemic alcohols via selective oxidation. This review includes the details of these biotransformations, catalyzed by whole cells (wild type and recombinant strains), purified enzymes (oxidoreductases) and immobilized whole cells of C. parapsilosis. The review presents a bioorganic perspective as it discusses the chemo, regio and stereoselectivity of the biocatalyst along with the structure of the substrates and optical purity of the products. Fermentation scale biocatalysis using whole cells of C. parapsilosis for several biotransformations to synthesize important chiral synthons/industrial chemicals is included. A comparison of C. parapsilosis with other whole cell biocatalysts for biocatalytic deracemization and asymmetric reduction of carbonyl and imine groups in the synthesis of a variety of enantiopure products is presented which will provide a basis for the choice of a biocatalyst for a desired organic transformation. Thus, a wholesome perspective on the present status of C. parapsilosis mediated organic transformations and design of new reactions which can be considered for large scale operations is provided. Taken together, C. parapsilosis can now be considered a ‘reagent’ for the organic transformations discussed here. © 2016 Elsevier Inc.

Bioorganic Chemistry

Candida parapsilosis: A versatile biocatalyst for organic oxidation-reduction reactions

Biocatalytic deracemisation of a range of racemic (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates using Candida parapsilosis ATCC 7330 resulted in pure (S)-enantiomers in yields of up to 80% and ee>99%. © 2007 Elsevier Ltd. All rights reserved.

Tetrahedron

Preparation of optically pure (3E,5E)-alkyl-2-hydroxy-6-arylhexa-3,5-dienoates by Candida parapsilosis ATCC 7330 mediated deracemisation of the racemates

Enantioselective bioreduction of alkyl 2-oxo-4-arylbutanoates and 2-oxo-4-arylbut-3-enoates mediated by Candida parapsilosis ATCC 7330 resulted in the formation of the corresponding (S)-2-hydroxy compounds in high enantiomeric excesses (93-99%) and good isolated yields (58-71%). The absolute configuration of enantiomerically pure ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate obtained by the reduction of the corresponding keto ester was assigned by 1H NMR using Mosher's method. © 2004 Elsevier Ltd. All rights reserved.

Tetrahedron Asymmetry

Asymmetric reduction of alkyl 2-oxo-4-arylbutanoates and -but-3-enoates by Candida parapsilosis ATCC 7330: Assignment of the absolute configuration of ethyl 2-hydroxy-4-(p-methylphenyl)but-3-enoate by 1H NMR

Biocatalytic deracemisaton of the racemic ethyl ester of 2-hydroxy-4-phenylbutanoic acid gives the (S)-enantiomer exclusively in >99% e.e. and 85-90% yield. Ethyl and methyl esters of mandelic acid and the methyl ester of 2-hydroxy-4-phenylbutanoic acid also gave the (S)-enantiomer exclusively. Whole cells of Candida parapsilosis (ATCC 7330) were used to effect this biotansformation. © 2002 Published by Elsevier Science Ltd.

Biocatalytic deracemisation of α-hydroxy esters: High yield preparation of (S)-ethyl 2-hydroxy-4-phenylbutanoate from the racemate

ChemInform

ChemInform Abstract: Biotransformations by Plant Cell Cultures.

Dynamic thermodynamic resolution of N-methylpseudoephedrine α-bromo esters for asymmetric syntheses of α-hydroxy carboxylic acid derivatives

Tetrahedron: Asymmetry

Enantioselective hydrolysis of 1-aryl ethyl acetates and reduction of aryl methyl ketones using carrot, celeriac and horseradish enzyme systems

Stereoselective synthesis of (R)-(−)-denopamine, (R)-(−)-tembamide and (R)-(−)-aegeline via asymmetric reduction of azidoketones by Daucus carota in aqueous medium

Highly stereoselective reduction of 4-Aryl-2-oxo but-3-enoic carboxylic esters by plant cell culture of Daucus carota

Journal	Data powered by TypesetJournal of Molecular Catalysis B: Enzymatic
Publisher	Data powered by TypesetElsevier
ISSN	13811177
Open Access	No