Conformational analysis of peptides containing enantiomerically pure alpha-methylasparagine: Correspondence between computed and solid state structures

Authors
Hopkins, SA Konopelski, JP Olmstead, MM Banks, HD
Citation
Sa. Hopkins et al., Conformational analysis of peptides containing enantiomerically pure alpha-methylasparagine: Correspondence between computed and solid state structures, TETRAHEDRON, 56(50), 2000, pp. 9733-9737
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
50
Year of publication
2000
Pages
9733 - 9737
Database
ISI
SICI code
0040-4020(200012)56:50<9733:CAOPCE>2.0.ZU;2-O
Abstract
Asparagine has a high frequency of occurrence in beta -turns. We have recen tly completed an asymmetric synthesis of alpha -methylasparagine suitably p rotected for incorporation into polypeptides, and report herein the synthes is and structure of dipeptide Ac-Ala-(Me)Asn-NHMe (1). The synthesis procee ds through the corresponding alpha -methylasparagine succinimide derivative . The three-dimensional structure of the dipeptide around the alpha,alpha - dialkylated alpha -amino acid is compared to that predicted for Ac-(Me)Asn- NHMe. (C) 2000 Elsevier Science Ltd. All rights reserved.