| Stereochemistry of sagittamide A: prediction and confirmation. | |
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MedLine Citation:
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PMID: 16898837 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[structure: see text] The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the 3JH,H profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed 1H NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product. |
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Authors:
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Hirofumi Seike; Indranath Ghosh; Yoshito Kishi |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Organic letters Volume: 8 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2006 Aug |
Date Detail:
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Created Date: 2006-08-10 Completed Date: 2007-06-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 3865-8 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Biological Products
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chemistry Molecular Structure Nuclear Magnetic Resonance, Biomolecular Ornithine / analogs & derivatives*, chemistry Stereoisomerism Valine / analogs & derivatives*, chemistry |
| Chemical | |
Reg. No./Substance:
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0/Biological Products; 0/sagittamide A; 7004-03-7/Valine; 7006-33-9/Ornithine |
| Comments/Corrections | |
Erratum In:
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Org Lett. 2006 Oct 26;8(22):5177 |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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