Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum
dc.contributor.author | Sunderhaus, James D. | en_US |
dc.contributor.author | Sherman, David H. | en_US |
dc.contributor.author | Williams, Robert M. | en_US |
dc.date.accessioned | 2011-05-06T15:39:42Z | |
dc.date.available | 2012-05-14T20:40:08Z | en_US |
dc.date.issued | 2011-04 | en_US |
dc.identifier.citation | Sunderhaus, James D.; Sherman, David H.; Williams, Robert M. (2011). "Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum." Israel Journal of Chemistry 51(3-4): 442-452. <http://hdl.handle.net/2027.42/83757> | en_US |
dc.identifier.issn | 0021-2148 | en_US |
dc.identifier.issn | 1869-5868 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/83757 | |
dc.description.abstract | The stephacidin and notoamide natural products belong to a group of prenylated indole alkaloids containing a bicyclo[2.2.2]diazaoctane core. Biosynthetically, this bicyclic core is believed to be the product of an intermolecular Diels–Alder (IMDA) cycloaddition of an achiral azadiene. Since all of the natural products in this family have been isolated in enantiomerically pure form to date, it is believed that an elusive Diels–Alderase enzyme mediates the IMDA reaction. Adding further intrigue to this biosynthetic puzzle is the fact that several related Aspergillus fungi produce a number of metabolites with the opposite absolute configuration, implying that these fungi have evolved enantiomerically distinct Diels–Alderases. We have undertaken a program to identify every step in the biogenesis of the stephacidins and notoamides, and by combining the techniques of chemical synthesis and biochemical analysis we have been able to identify the two prenyltransferases involved in the early stages of the stephacidin and notoamide biosyntheses. This has allowed us to propose a modified biosynthesis for stephacidin A, and has brought us closer to our goal of finding evidence for, or against, the presence of a Diels–Alderase in this biosynthetic pathway. | en_US |
dc.publisher | WILEY-VCH Verlag | en_US |
dc.subject.other | Chemistry | en_US |
dc.subject.other | General Chemistry | en_US |
dc.title | Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Life Sciences Institute and Departments of Medicinal Chemistry, Microbiology & Immunology, and Chemistry, University of Michigan, Ann Arbor, MI 48109-2216, USA | en_US |
dc.contributor.affiliationother | Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA phone: 14+1 14970-491-6747 fax: 14+1 14970-491-3944 | en_US |
dc.contributor.affiliationother | Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA phone: 14+1 14970-491-6747 fax: 14+1 14970-491-3944 ; University of Colorado Cancer Center, Aurora, CO 80045, USA ; Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA phone: 14+1 14970-491-6747 fax: 14+1 14970-491-3944 | en_US |
dc.identifier.pmid | 21818159 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/83757/1/442_ftp.pdf | |
dc.identifier.doi | 10.1002/ijch.201100016 | en_US |
dc.identifier.source | Israel Journal of Chemistry | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
Files in this item
Remediation of Harmful Language
The University of Michigan Library aims to describe library materials in a way that respects the people and communities who create, use, and are represented in our collections. Report harmful or offensive language in catalog records, finding aids, or elsewhere in our collections anonymously through our metadata feedback form. More information at Remediation of Harmful Language.
Accessibility
If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.