Xin, Meite and Bugg, Tim. (2010) Biomimetic formation of 2-tropolones by dioxygenase-catalysed ring expansion of substituted 2,4-cyclohexadienones. ChemBioChem, Vol.11 (No.2). pp. 272-276. ISSN 1439-4227

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Abstract

Substituted 2-tropolone natural products, are found in plants and fungi. Their biosynthesis is thought to occur by ring expansion from a cyclohexadienone precursor, but this reaction has not previously been demonstrated experimentally. Treatment of 6-hydroxy-6-hydroxymethylcyclohexa-2,4-dienone with the non-haem iron(II)-dependent extradiol catechol dioxygenase MhpB from Escherichia coli results in the formation of the 2-tropolone ring-expansion product through a pinacol-type rearrangement. Three further substituted cyclohexa-2,4-dienone analogues were prepared, and treatment of each analogue was found to give the substituted 2-tropolone ring-expansion product. This ring expansion could also be effected nonenzymatically by treatment with. 1,4,7-triazacyclonone and FeCl2. This is a novel transformation for non-haem iron-dependent enzymes, and this is the first experimental demonstration of the proposed ring-expansion reaction in tropolone biosynthesis.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry Q Science > QP Physiology
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Biomimetics, Pinacol rearrangement, Ring formation (Chemistry), Biosynthesis
Journal or Publication Title:	ChemBioChem
Publisher:	Wiley - V C H Verlag GmbH & Co. KGaA
ISSN:	1439-4227
Date:	25 January 2010
Volume:	Vol.11
Number:	No.2
Number of Pages:	5
Page Range:	pp. 272-276
Identification Number:	10.1002/cbic.200900631
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
URI:	http://wrap.warwick.ac.uk/id/eprint/6497

Data sourced from Thomson Reuters' Web of Knowledge

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