Towards hydroxylated nylon 6: linear and cyclic oligomers from a protected 6-amino-6-deoxy-DD galactonate––a novel class of carbopeptoid-cyclodextrin (CPCD)

Mayes, Benjamin A. and Stetz, Rebecca J.E. and Watterson, Mark P. and Edwards, Alison A. and Ansell, Christopher W.G. and Tranter, George E. and Fleet, George W.J. (2004) Towards hydroxylated nylon 6: linear and cyclic oligomers from a protected 6-amino-6-deoxy-DD galactonate––a novel class of carbopeptoid-cyclodextrin (CPCD). Tetrahedron: Asymmetry, 15 (4). pp. 627-638. ISSN 0957-4166 . (Access to this publication is restricted)

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http://dx.doi.org/10.1016/j.tetasy.2003.12.031

Abstract

Circular dichroism studies on a series of linear oligomers derived from a protected 6-amino-6-deoxy-D-galactonate (an epsilon-amino acid) indicated a predisposition to form a rigid structure in solution, which is comparable to a beta-sheet composed of L-amino acids; in contrast, a diastereomeric allonate series provided no evidence for secondary structure. A linear tetramer was cyclised to a 28-membered ring lactam in modest yield, which on deprotection formed a class of macrocycle with structural features of both a cyclic peptide and a cyclodextrin.

Item Type: Article
Subjects: Q Science
Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > Medway School of Pharmacy
Depositing User: Alison Edwards
Date Deposited: 05 Sep 2008 12:56
Last Modified: 14 Apr 2014 13:13
Resource URI: http://kar.kent.ac.uk/id/eprint/4886 (The current URI for this page, for reference purposes)
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