Optically pure aliphatic β-hydroxy esters were prepared from their racemates by deracemisation using the biocatalyst Candida parapsilosis ATCC 7330. High optical purity (up to >99 %) and good yields (up to 71 %) of the product secondary alcohols were obtained. This study highlights the importance of optimization of reaction conditions using ethyl-3-hydroxybutanoate as the model substrate to improve the enantioselectivity (enantiomeric excess from 9 to 98 %). The present study emphasises the broad substrate scope of the biocatalyst towards deracemisation. This is the first report of Candida parapsilosis ATCC 7330-mediated deracemisation of various alkyl-3-hydroxybutanoates to produce either the (R)-enantiomers (methyl, ethyl, propyl, butyl, t-butyl, allyl-3-hydroxybutanoates) or (S)-enantiomers (pentyl, iso-amyl and iso-propyl-3-hydroxybutanoates). © 2014, Society for Industrial Microbiology and Biotechnology.

Anju Chadha

Department Of Biotechnology

ALIPHATIC BETA HYDROXY ESTER

Aliphatic compound

ALKYL 3 HYDROXYBUTANOATE

alkyl group

ester derivative

unclassified drug

butyric acid derivative

ester

hydroxybutyric acid

article

Biocatalysis

Biocatalyst

biotransformation

CANDIDA PARAPSILOSIS

CANDIDA PARAPSILOSIS ATCC 7330

cell viability

controlled study

enantiomer

Enantioselectivity

nonhuman

oxidation reduction reaction

reaction optimization

reaction time

solubility

Candida

chemistry

enzyme specificity

metabolism

Microbial Viability

Stereoisomerism

Butyrates

Esters

Hydrogen-Ion Concentration

Hydroxybutyrates

Substrate Specificity

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 Industrial Microbiology and Biotechnology

The cell free extracts of Candida parapsilosis ATCC 7330 are more efficient than the whole resting cells of the yeast in the synthesis of directly usable gold nanoparticles as revealed by this systematic study. Cell free extracts yielded gold nanoparticles of hydrodynamic diameter (50–200 nm). In this study, the total protein concentration influences the nanofabrication and not only the reductase enzymes as originally thought. Powder X-ray diffraction studies confirm the crystalline nature of the gold nanoparticles. Fourier Transform Infra Red spectroscopy and thermal gravimetric analysis suggests that the biosynthesized gold nanoparticles are capped by peptides/proteins. Dispersion experiments indicate a stable dispersion of gold nanoparticles in pH 12 solutions which is also confirmed by electron microscopic analysis and validated using a surface plasmon resonance assay. The effectiveness of the dispersed nanoparticles for the reduction of 4-nitrophenol using sodium borohydride as a reductant further confirms the formation of functional gold nanoparticles. It is also reported that gold nanoparticles with mean particle diameter of 27 nm are biosynthesized inside the whole cell by transmission electron microscopy analysis. With optimized reaction conditions, maximum gold bioaccumulation with the 24 h culture age of the yeast with cellular uptake of ~1010 gold atoms at the single cell level is achieved but it is not easy to extract the gold nanoparticles from the whole resting cells. © 2016, The Author(s).

Fulltext

AMB Express

Whole resting cells vs. cell free extracts of Candida parapsilosis ATCC 7330 for the synthesis of gold nanoparticles

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.

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

A green, simple and high yielding [up to 86% yield] procedure is developed for the oxidation of aromatic (activated) primary alcohols to aldehydes using whole cells of Candida parapsilosis ATCC 7330. The biotransformation is carried out under mild conditions at 25 °C, in hexane: water (48 : 2) (v/v). © The Royal Society of Chemistry.

Candida parapsilosis ATCC 7330 mediated oxidation of aromatic (activated) primary alcohols to aldehydes

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

Journal	Data powered by TypesetJournal of Industrial Microbiology and Biotechnology
Publisher	Data powered by TypesetSpringer Verlag
ISSN	13675435
Open Access	No