A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

Ricardo G. Alvarez; Iain S. Hunter; Colin J. Suckling; Michael Thomas; Ute Vitinius

doi:10.1016/S0040-4020(01)00837-7

A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

Ricardo G. Alvarez, Iain S. Hunter, Colin J. Suckling, Michael Thomas, Ute Vitinius

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

23 Citations (Scopus)

Abstract

Abstract The oxidation of 3-alkyl benzofurans, indoles, and a benzothiophene by the chloroperoxidase from Caldariomyces fumago has been investigated. Under conditions in which the catalase activity of chloroperoxidase was minimised in the presence of chloride and hydrogen peroxide, 3-methylbenzothiophene was oxidised at sulfur but the indoles (5-9) and benzofurans (1-4) gave 2,3-diols as initial products. In the case of N-unsubstituted indoles, these tautomerised to give the corresponding lactam. In contrast, the diols (predominantly trans) formed from the benzofurans were sufficiently stable for isolation and full characterisation. This novel reaction has the potential to be developed into a useful synthetic biotransformation.

Original language	English
Pages (from-to)	8581-8587
Number of pages	6
Journal	Tetrahedron
Volume	57
Issue number	40
DOIs	https://doi.org/10.1016/S0040-4020(01)00837-7
Publication status	Published - Oct 2001

Keywords

biotransformations
chloroperoxidases
benzofurans
dihydroxylation

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10.1016/S0040-4020(01)00837-7

http://dx.doi.org/10.1016/S0040-4020(01)00837-7

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title = "A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase",

abstract = "Abstract The oxidation of 3-alkyl benzofurans, indoles, and a benzothiophene by the chloroperoxidase from Caldariomyces fumago has been investigated. Under conditions in which the catalase activity of chloroperoxidase was minimised in the presence of chloride and hydrogen peroxide, 3-methylbenzothiophene was oxidised at sulfur but the indoles (5-9) and benzofurans (1-4) gave 2,3-diols as initial products. In the case of N-unsubstituted indoles, these tautomerised to give the corresponding lactam. In contrast, the diols (predominantly trans) formed from the benzofurans were sufficiently stable for isolation and full characterisation. This novel reaction has the potential to be developed into a useful synthetic biotransformation.",

keywords = "biotransformations, chloroperoxidases, benzofurans, dihydroxylation",

author = "Alvarez, {Ricardo G.} and Hunter, {Iain S.} and Suckling, {Colin J.} and Michael Thomas and Ute Vitinius",

year = "2001",

month = oct,

doi = "10.1016/S0040-4020(01)00837-7",

language = "English",

volume = "57",

pages = "8581--8587",

journal = "Tetrahedron",

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TY - JOUR

T1 - A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

AU - Alvarez, Ricardo G.

AU - Hunter, Iain S.

AU - Suckling, Colin J.

AU - Thomas, Michael

AU - Vitinius, Ute

PY - 2001/10

Y1 - 2001/10

N2 - Abstract The oxidation of 3-alkyl benzofurans, indoles, and a benzothiophene by the chloroperoxidase from Caldariomyces fumago has been investigated. Under conditions in which the catalase activity of chloroperoxidase was minimised in the presence of chloride and hydrogen peroxide, 3-methylbenzothiophene was oxidised at sulfur but the indoles (5-9) and benzofurans (1-4) gave 2,3-diols as initial products. In the case of N-unsubstituted indoles, these tautomerised to give the corresponding lactam. In contrast, the diols (predominantly trans) formed from the benzofurans were sufficiently stable for isolation and full characterisation. This novel reaction has the potential to be developed into a useful synthetic biotransformation.

AB - Abstract The oxidation of 3-alkyl benzofurans, indoles, and a benzothiophene by the chloroperoxidase from Caldariomyces fumago has been investigated. Under conditions in which the catalase activity of chloroperoxidase was minimised in the presence of chloride and hydrogen peroxide, 3-methylbenzothiophene was oxidised at sulfur but the indoles (5-9) and benzofurans (1-4) gave 2,3-diols as initial products. In the case of N-unsubstituted indoles, these tautomerised to give the corresponding lactam. In contrast, the diols (predominantly trans) formed from the benzofurans were sufficiently stable for isolation and full characterisation. This novel reaction has the potential to be developed into a useful synthetic biotransformation.

KW - biotransformations

KW - chloroperoxidases

KW - benzofurans

KW - dihydroxylation

UR - http://dx.doi.org/10.1016/S0040-4020(01)00837-7

U2 - 10.1016/S0040-4020(01)00837-7

DO - 10.1016/S0040-4020(01)00837-7

M3 - Article

VL - 57

SP - 8581

EP - 8587

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 40

ER -