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Biomimetic formation of 2-tropolones by dioxygenase-catalysed ring expansion of substituted 2,4-cyclohexadienones
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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. doi:10.1002/cbic.200900631 ISSN 1439-4227.
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Official URL: http://dx.doi.org/10.1002/cbic.200900631
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 | ||||
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Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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Divisions: | Faculty of Science, Engineering and Medicine > 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 | ||||
Official Date: | 25 January 2010 | ||||
Dates: |
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Volume: | Vol.11 | ||||
Number: | No.2 | ||||
Number of Pages: | 5 | ||||
Page Range: | pp. 272-276 | ||||
DOI: | 10.1002/cbic.200900631 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
Data sourced from Thomson Reuters' Web of Knowledge
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