| Diastereoselective Pictet-Spengler approach for the synthesis of pyrrolo[3,2-e][1,4]diazepin-2-one peptide turn mimics. | |
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MedLine Citation:
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PMID: 18543989 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Sixteen pyrrolo[3,2- e][1,4]diazepin-2-ones 1 were synthesized in 4-5 steps and 5-48% overall yields from 4-oxoproline 8 by a route featuring a diastereoselective Pictet-Spengler reaction to close the seven-membered diazepinone ring. Crystallographic analysis of pyrrolo[3,2- e][1,4]diazepin-2-one 1b by X-ray diffraction demonstrated that the alpha-amino acid residue adopted dihedral angle geometry similar to an ideal gamma-turn, illustrating the potential for employing these novel heterocycles as peptide turn mimics. |
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Authors:
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Philippe Deaudelin; William D Lubell |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-06-11 |
Journal Detail:
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Title: Organic letters Volume: 10 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2008 Jul |
Date Detail:
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Created Date: 2008-06-26 Completed Date: 2008-09-16 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: 2841-4 Citation Subset: IM |
Affiliation:
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Département de chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec, Canada, H3C 3J7. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkenes
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chemistry Amides / chemistry Amination Azepines / chemistry* Biomimetic Materials / chemical synthesis*, chemistry Crystallography, X-Ray Models, Molecular Molecular Structure Peptides / chemical synthesis*, chemistry Pyrroles / chemistry* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Alkenes; 0/Amides; 0/Azepines; 0/Peptides; 0/Pyrroles |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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