| Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate. | |
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MedLine Citation:
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PMID: 22455514 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The crystal structure of 2-methylisoborneol synthase (MIBS) from Streptomyces coelicolor A3(2) has been determined in complex with substrate analogues geranyl-S-thiolodiphosphate and 2-fluorogeranyl diphosphate at 1.80 and 1.95 Å resolution, respectively. This terpenoid cyclase catalyzes the cyclization of the naturally occurring, noncanonical C-methylated isoprenoid substrate, 2-methylgeranyl diphosphate, to form the bicyclic product 2-methylisoborneol, a volatile C(11) homoterpene alcohol with an earthy, musty odor. While MIBS adopts the tertiary structure of a class I terpenoid cyclase, its dimeric quaternary structure differs from that previously observed in dimeric terpenoid cyclases from plants and fungi. The quaternary structure of MIBS is nonetheless similar in some respects to that of dimeric farnesyl diphosphate synthase, which is not a cyclase. The structures of MIBS complexed with substrate analogues provide insights regarding differences in the catalytic mechanism of MIBS and the mechanisms of (+)-bornyl diphosphate synthase and endo-fenchol synthase, plant cyclases that convert geranyl diphosphate into products with closely related bicyclic bornyl skeletons, but distinct structures and stereochemistries. |
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Authors:
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Mustafa Köksal; Wayne K W Chou; David E Cane; David W Christianson |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2012-03-28 |
Journal Detail:
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Title: Biochemistry Volume: 51 ISSN: 1520-4995 ISO Abbreviation: Biochemistry Publication Date: 2012 Apr |
Date Detail:
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Created Date: 2012-04-10 Completed Date: 2012-06-15 Revised Date: 2013-04-15 |
Medline Journal Info:
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Nlm Unique ID: 0370623 Medline TA: Biochemistry Country: United States |
Other Details:
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Languages: eng Pagination: 3011-20 Citation Subset: IM |
Copyright Information:
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© 2012 American Chemical Society |
Affiliation:
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Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Bacterial Proteins
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chemistry*,
metabolism Binding Sites Bornanes / chemistry*, metabolism Crystallography, X-Ray Cyclization Models, Molecular Monoterpenes / chemistry*, metabolism Protein Conformation Streptomyces coelicolor / enzymology*, metabolism |
| Grant Support | |
ID/Acronym/Agency:
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GM30301/GM/NIGMS NIH HHS; GM56838/GM/NIGMS NIH HHS; R01 GM030301/GM/NIGMS NIH HHS; R01 GM030301-29/GM/NIGMS NIH HHS; R01 GM030301-30/GM/NIGMS NIH HHS; R01 GM056838/GM/NIGMS NIH HHS; R01 GM056838-15/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Bacterial Proteins; 0/Bornanes; 0/Monoterpenes; 2371-42-8/2-methylisoborneol |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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