| Cyclization of peptoids by formation of boronate esters. | |
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MedLine Citation:
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PMID: 22611292 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Introduction of conformational constraints into peptoids (N-substituted oligoglycines) will enable new applications in molecular recognition and self-assembly. Peptoids that contain both a phenylboronic acid side chain and a vicinal diol cyclize by intramolecular condensation to form boronate esters. A fluorescent indicator of free boronic acid was used to assay esterification. A galactose moiety 2 to 5 monomer units away from a boronic acid side chain in a peptoid reacts with the boronic acid in competition with the indicator. The intramolecular reaction predominates in each case, with 80-90% of the peptoid cyclized. When the diol is a simple 2,3-dihydroxypropyl group, esterification is less favored but still appreciable. |
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Authors:
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Sara Chirayil; Kevin J Luebke |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-12-8 |
Journal Detail:
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Title: Tetrahedron letters Volume: 53 ISSN: 0040-4039 ISO Abbreviation: - Publication Date: 2012 Feb |
Date Detail:
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Created Date: 2012-5-21 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2984819R Medline TA: Tetrahedron Lett Country: - |
Other Details:
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Languages: ENG Pagination: 726-729 Citation Subset: - |
Affiliation:
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Division of Cardiology, Department of Internal Medicine, University of Texas Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, Texas, 75390-8573 USA. |
Export Citation:
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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