Document Detail


1H-Azepine-4-amino-4-carboxylic Acid: A New α,α-Disubstituted Ornithine Analogue Capable of Inducing Helix Conformations in Short Ala-Aib Pentapeptides.
MedLine Citation:
PMID:  22689465     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A very efficient synthesis of orthogonally protected 1H-azepine-4-amino-4-carboxylic acid, abbreviated as Azn, a conformationally restricted analogue of ornithine, was realized. It was obtained on a gram scale in good overall yield in five steps, three of which did not require isolation of the intermediates, starting from the readily available 1-amino-4-oxo-cyclohexane-4-carboxylic acid. Both enantiomers were used for the preparation of pentapeptide models containing Ala, Aib, and Azn. Conformational studies using both spectroscopic techniques (NMR, CD) and molecular dynamics on model 5-mer peptides showed that the (R)-Azn isomer possesses a marked helicogenic effect.
Authors:
Sara Pellegrino; Alessandro Contini; Francesca Clerici; Alessandro Gori; Donatella Nava; Maria Luisa Gelmi
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-6-11
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2012 Jun 
Date Detail:
Created Date:  2012-6-12     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
DISMAB, Sezione di Chimica Organica "A. Marchesini", Facoltà di Farmacia, Università degli Studi Milano, Via Venezian 21, 20133 Milano (Italy), Fax: (+39) 02-50314476. sara.pellegrino@unimi.it.
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