Racemic alkyl-2-hydroxy-4-arylbut-3-ynoates were deracemized to the (S)-alkyl-2-hydroxy-4-arylbut-3-ynoates in excellent enantiomeric excesses (up to &gt;99%) and good isolated yields (up to 81%) with the biocatalyst Candida parapsilosis ATCC 7330. The absolute configuration of the resulting enantiomer was assigned by 1H NMR using Mosher's method. © 2010 Elsevier Ltd. All rights reserved.

Anju Chadha

Department Of Biotechnology

ALKYL 2 HYDROXY 4 ARYLBUT 3 YNOATE

ALLYL 2 HYDROXY 4 PHENYLBUT 3 YNOATE

BUTYL 2 HYDROXY 4 PHENYLBUT 3 YNOATE

ETHYL 2 HYDROXY 4 2 TOLYLBUT 3 YNOATE

ETHYL 2 HYDROXY 4 4 TOLYLBUT 3 YNOATE

ETHYL 2 HYDROXY 4 PHENYLBUT 3 YNOATE

ETHYL 2 OXO 4 2 TOLYLBUT 3 YNOATE

ETHYL 4 (2 CHLOROPHENYL) 2 HYDROXYBUT 3 YNOATE

ETHYL 4 (2 CHLOROPHENYL) 2 OXOBUT 3 YNOATE

ETHYL 4 (2 METHOXYPHENYL) 2 HYDROXYBUT 3 YNOATE

ETHYL 4 (2 METHOXYPHENYL) 2 OXOBUT 3 YNOATE

ETHYL 4 (4 METHOXYPHENYL) 2 HYDROXYBUT 3 YNOATE

ETHYL 4 (4 NITROPHENYL) 2 HYDROXYBUT 3 YNOATE

hydroxyl group

ISOPROPYL 2 HYDROXY 4 PHENYLBUT 3 YNOATE

METHYL 2 HYDROXY 4 PHENYLBUT 3 YNOATE

PROP 2 YNYL 2 HYDROXY 4 PHENYLBUT 3 YNOATE

PROPYL 2 HYDROXY 4 PHENYLBUT 3 YNOATE

unclassified drug

article

Biocatalyst

CANDIDA PARAPSILOSIS

chemical structure

enantiomer

Enantioselectivity

high performance liquid chromatography

nonhuman

oxidation reduction reaction

priority journal

proton nuclear magnetic resonance

RACEMIZATION

synthesis

X ray crystallography

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

Tetrahedron Asymmetry

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

Confocal microscopic studies with the resting cells of yeast, Candida parapsilosis ATCC 7330, a reportedly versatile biocatalyst for redox enzyme mediated preparation of optically pure secondary alcohols in high optical purities [enantiomeric excess (ee) up to >99%] and yields, revealed that the yeast cells had large vacuoles under the experimental conditions studied where the redox reaction takes place. A novel fluorescence method was developed using 1-(6-methoxynaphthalen-2-yl)ethanol to track the site of biotransformation within the cells. This alcohol, itself non-fluorescent, gets oxidized to produce a fluorescent ketone, 1-(6-methoxynaphthalen-2-yl)ethanone. Kinetic studies showed that the reaction occurs spontaneously and the products get released out of the cells in less time [5 mins]. The biotransformation was validated using HPLC.

Fulltext

Scientific Reports

Direct observation of redox reactions in Candida parapsilosis ATCC 7330 by Confocal microscopic studies

Enantiomerically pure β- and γ-nitro alcohols were prepared from their respective nitro ketones by asymmetric reduction mediated by the biocatalyst, Candida parapsilosis ATCC 7330 under optimized reaction conditions (ee up to >99%; yields up to 76%). This biocatalyst exhibits high chemoselectivity and reduces the keto group in preference to nitro group along with good enantioselectivity to produce enantiomerically enriched nitro alkanols. The asymmetric reduction of aliphatic nitro ketones was carried out in water with ethanol as cosolvent and glucose as cosubstrate using the whole cells of Candida parapsilosis ATCC 7330 in much lesser time (4 h). For the first time, the biocatalytic asymmetric reduction of the following ketones is reported here: 1-nitro-butan-2-one, 1-nitro-pentan-2-one, 3-methyl-1-nitro-butan-2-one and 1-cyclohexyl-2-nitroethanone to produce (R)-alcohols [ee up to 79%, yield up to 74%] and 1-nitro-hexan-2-one and 1-nitro-heptan-2-one to produce (S)-alcohols [ee up to 81%, yield up to 76%]. © The Royal Society of Chemistry.

RSC Advances

Enantio- &amp; chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330

Optically pure (S)-ethyl 3-hydroxy 4,4,4-trifluorobutanoate was prepared using the biocatalyst Candida parapsilosis ATCC 7330 by deracemisation of the racemic alcohol ester in high optical purity (96%) and yield (65%) and by asymmetric reduction from its prochiral ketone (ee up to 84% and yield 60%) under different reaction conditions. This study highlights the possibility of using the same biocatalyst to produce (S)-ethyl 3-hydroxy 4,4,4-trifluorobutanoate using different strategies. ©2014 Elsevier B.V. All rights reserved.

Journal of Fluorine Chemistry

Preparation of enantiomerically enriched (S)-ethyl 3-hydroxy 4,4,4-trifluorobutanoate using whole cells of Candida parapsilosis ATCC 7330

Various aryl and alkyl substituted optically pure propargyl alcohols were obtained with excellent ee (up to >99%) and isolated yields (up to 87%) by deracemization using whole cells of Candida parapsilosis ATCC 7330. The whole cells show substrate specificity towards alkyl substituted propargyl alcohols and a switch in the enantioselectivity has been observed from 'R' to 'S' upon increasing the chain length. For the first time, enantiopure (R)-4-(3-hydroxybut-1-ynyl)benzonitrile, (R)-4-(biphenyl-4-yl)but-3-yn-2-ol, (S)-ethyl 3-hydroxy-5-phenylpent-4-ynoate and (S)-4-phenylbut-3-yne-1,2-diol were obtained using this strategy. Optically pure propargyl alcohol thus obtained was used as a chiral starting material in the synthesis of enantiomerically enriched poly-substituted pyrrolidines and a pyrrole derivative successfully demonstrating a chemoenzymatic route. This journal is © 2014 the Partner Organisations.

Organic and Biomolecular Chemistry

Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines

Deracemisation of racemic (3E)-alkyl-4-(hetero-2-yl)-2-hydroxybut-3-enoates using Candida parapsilosis ATCC 7330 resulted in the formation of one enantiomer in high enantiomeric excess [up to &gt;99% ee] and isolated yields [up to 79%]. The absolute configuration of the enantiomerically pure (3E)-ethyl-4-(thiophene-2-yl)-2-hydroxybut-3-enoate as determined by 1H NMR of the Mosher esters was found to be (S). © 2007 Elsevier Ltd. All rights reserved.

Preparation of enantiomerically pure (3E)-alkyl-4-(hetero-2-yl)-2-hydroxybut-3-enoates by Candida parapsilosis ATCC 7330 mediated deracemisation and determination of the absolute configuration of (3E)-ethyl-4-(thiophene-2-yl)-2-hydroxybut-3-enoate

Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl α-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted α-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. © 2005 Elsevier Ltd. All rights reserved.

Tetrahedron

Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: Effect of substrate structure and mechanism

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.

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

Tetrahedron: Asymmetry

Mechanistic investigation of the Candida albicans CCT 0776 stereoinversion system and application to obtain enantiopure secondary alcohols

Biocatalytic deracemization of alkyl-2-hydroxy-4-arylbut-3-ynoates using whole cells of Candida parapsilosis ATCC 7330

Journal	Tetrahedron Asymmetry
ISSN	09574166
Open Access	No