| Chirospecific synthesis of spirocyclic beta-lactams and their characterization as potent type II beta-turn inducing peptide mimetics. | |
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MedLine Citation:
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PMID: 16388623 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[reaction: see text] Starting from natural proline, a practical chirospecific synthesis of spirocyclic beta-lactams of type 2 is described when a methylene moiety showing minimal steric demand is employed as a constraint element for adjusting the dihedral angle psi(i + 1). Employing the concept of self-reproduction of chirality, C-formylation of the oxazolidinone 5 afforded the key intermediate 7 taking advantage of an intermediate protection of the bridging element as a vinyl moiety. NMR- and IR-based conformational studies clearly indicated that spiro-beta-lactams of type 2 can serve as efficient beta-turn nucleators. |
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Authors:
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Holger Bittermann; Peter Gmeiner |
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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: The Journal of organic chemistry Volume: 71 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2006 Jan |
Date Detail:
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Created Date: 2006-01-03 Completed Date: 2006-07-26 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 97-102 Citation Subset: IM |
Affiliation:
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Department of Medicinal Chemistry, Emil Fischer Center, Friedrich Alexander University, Schuhstrasse 19, D-91052 Erlangen, Germany. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Biomimetic Materials
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chemical synthesis*,
chemistry Cyclization Magnetic Resonance Spectroscopy Molecular Structure Peptides / chemistry* Spectrophotometry, Infrared beta-Lactams / chemical synthesis, chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Peptides; 0/beta-Lactams |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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