| Nocardiopsins: new FKBP12-binding macrolide polyketides from an Australian marine-derived actinomycete, Nocardiopsis sp. | |
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MedLine Citation:
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PMID: 20112311 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A marine-derived actinomycete, Nocardiopsis sp. (CMB-M0232), obtained from a sediment sample collected at a depth of 55 m off the coast of Brisbane, Australia, yielded two new macrolide polyketides. Structures for nocardiopsins A and B were assigned by detailed spectroscopic analysis, degradation and chemical derivatization. A Marfey's analysis revealed an unexpected acid-mediated partial racemization of the L-pipecolic acid incorporated within the nocardiopsins. The scope of this racemization was assessed against a selection of natural and synthetic N-acyl pipecolic acids. While the nocardiopsins are not antibacterial, antifungal or cytotoxic, they do exhibit low-micromolar binding to the immunophilin FKBP12, consistent with their structural and biosynthetic relationship to the immunosuppressive agents FK506 and rapamycin. The nocardiopsins represent a new point of entry into what has been a valuable, exclusive and reclusive region of bioactive chemical space--that surrounding the FK506/rapamycin pharmacophore. |
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Authors:
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Ritesh Raju; Andrew M Piggott; Melissa Conte; Zakir Tnimov; Kirill Alexandrov; Robert J Capon |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 16 ISSN: 1521-3765 ISO Abbreviation: Chemistry Publication Date: 2010 Mar |
Date Detail:
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Created Date: 2010-03-08 Completed Date: 2010-04-20 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 3194-200 Citation Subset: IM |
Affiliation:
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Institute for Molecular Bioscience, The University of Queensland, Carmody Road, St. Lucia, Brisbane 4072, Australia. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Actinobacteria
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chemistry*,
isolation & purification* Animals Anti-Bacterial Agents / chemistry*, isolation & purification* Immunochemistry / methods Immunosuppressive Agents / chemistry* Macrolides / chemistry*, isolation & purification*, metabolism Marine Biology Molecular Structure Sirolimus / chemistry* Tacrolimus / chemistry* Tacrolimus Binding Protein 1A / chemistry*, isolation & purification*, metabolism |
| Chemical | |
Reg. No./Substance:
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0/Anti-Bacterial Agents; 0/Immunosuppressive Agents; 0/Macrolides; 0/nocardiopsin A; 0/nocardiopsin B; 109581-93-3/Tacrolimus; 53123-88-9/Sirolimus; EC 5.2.1.-/Tacrolimus Binding Protein 1A |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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