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Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines
Sushital Jana,
Published in Royal Society of Chemistry
2014
PMID: 24866773
Volume: 12
   
Issue: 26
Pages: 4682 - 4690
Abstract
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.
About the journal
JournalData powered by TypesetOrganic and Biomolecular Chemistry
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN14770520
Open AccessNo
Concepts (34)
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    Aromatic compounds
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    CANDIDA PARAPSILOSIS
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    CHEMO-ENZYMATIC SYNTHESIS
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    CHEMOENZYMATIC ROUTE
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    DE-RACEMIZATION
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    Isolated yield
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    Propargyl alcohol
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    PYRROLE DERIVATIVES
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    Substrate specificity
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    Enantiomers
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    Alkyne
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    Polycyclic hydrocarbon
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    Propanol
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    Pyrrolidine derivative
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    Biocatalysis
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    Candida
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    Chemistry
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    Conformation
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    Cytology
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    Enzymology
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    High performance liquid chromatography
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    Organic chemistry
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    Procedures
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    Stereoisomerism
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    Synthesis
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    X ray crystallography
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    Alkynes
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    Chemistry, organic
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    Chromatography, high pressure liquid
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    Crystallography, x-ray
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    Molecular conformation
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    Polycyclic compounds
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    PROPANOLS
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    Pyrrolidines