Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol

Pankaj P Daramwar; Prabhakar Lal Srivastava; Swati P Kolet; Hirekodathakallu V Thulasiram

doi:10.1039/c3ob42174k

Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol

Pankaj P Daramwar
, Prabhakar Lal Srivastava
, Swati P Kolet
, Hirekodathakallu V Thulasiram

CSIR-National Chemical Laboratory, Pune

Research output: Contribution to journal › Article › peer-review

Abstract

Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation on (Z)-α-santalol were achieved for the first time, using a fungal strain Mucor piriformis. Four novel metabolites were characterized as 10,11-cis-β-epoxy-α-santalol, 5α-hydroxy-(Z)-α-santalol, 10,11-dihydroxy-α-santalol and 5α-hydroxy-10,11-cis-β-epoxy-α-santalol. Using Amano PS lipase from Burkholderia cepacia, α- and β-isomers of 10,11-cis-epoxy-α-santalol were resolved efficiently.

Original language	English
Pages (from-to)	1048-51
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	7
DOIs	https://doi.org/10.1039/c3ob42174k
Publication status	Published - 21 Feb 2014
Externally published	Yes

Keywords

Biocatalysis
Burkholderia cepacia/enzymology
Hydroxylation
Lipase/metabolism
Molecular Conformation
Mucor/metabolism
Polycyclic Sesquiterpenes
Sesquiterpenes/metabolism
Stereoisomerism

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title = "Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol",

abstract = "Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation on (Z)-α-santalol were achieved for the first time, using a fungal strain Mucor piriformis. Four novel metabolites were characterized as 10,11-cis-β-epoxy-α-santalol, 5α-hydroxy-(Z)-α-santalol, 10,11-dihydroxy-α-santalol and 5α-hydroxy-10,11-cis-β-epoxy-α-santalol. Using Amano PS lipase from Burkholderia cepacia, α- and β-isomers of 10,11-cis-epoxy-α-santalol were resolved efficiently.",

keywords = "Biocatalysis, Burkholderia cepacia/enzymology, Hydroxylation, Lipase/metabolism, Molecular Conformation, Mucor/metabolism, Polycyclic Sesquiterpenes, Sesquiterpenes/metabolism, Stereoisomerism",

author = "Daramwar, \{Pankaj P\} and Srivastava, \{Prabhakar Lal\} and Kolet, \{Swati P\} and Thulasiram, \{Hirekodathakallu V\}",

year = "2014",

month = feb,

day = "21",

doi = "10.1039/c3ob42174k",

language = "English",

volume = "12",

pages = "1048--51",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol

AU - Daramwar, Pankaj P

AU - Srivastava, Prabhakar Lal

AU - Kolet, Swati P

AU - Thulasiram, Hirekodathakallu V

PY - 2014/2/21

Y1 - 2014/2/21

N2 - Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation on (Z)-α-santalol were achieved for the first time, using a fungal strain Mucor piriformis. Four novel metabolites were characterized as 10,11-cis-β-epoxy-α-santalol, 5α-hydroxy-(Z)-α-santalol, 10,11-dihydroxy-α-santalol and 5α-hydroxy-10,11-cis-β-epoxy-α-santalol. Using Amano PS lipase from Burkholderia cepacia, α- and β-isomers of 10,11-cis-epoxy-α-santalol were resolved efficiently.

AB - Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation on (Z)-α-santalol were achieved for the first time, using a fungal strain Mucor piriformis. Four novel metabolites were characterized as 10,11-cis-β-epoxy-α-santalol, 5α-hydroxy-(Z)-α-santalol, 10,11-dihydroxy-α-santalol and 5α-hydroxy-10,11-cis-β-epoxy-α-santalol. Using Amano PS lipase from Burkholderia cepacia, α- and β-isomers of 10,11-cis-epoxy-α-santalol were resolved efficiently.

KW - Biocatalysis

KW - Burkholderia cepacia/enzymology

KW - Hydroxylation

KW - Lipase/metabolism

KW - Molecular Conformation

KW - Mucor/metabolism

KW - Polycyclic Sesquiterpenes

KW - Sesquiterpenes/metabolism

KW - Stereoisomerism

U2 - 10.1039/c3ob42174k

DO - 10.1039/c3ob42174k

M3 - Article

C2 - 24407157

SN - 1477-0520

VL - 12

SP - 1048

EP - 1051

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 7

ER -

Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol

Abstract

Keywords

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