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., Stetz, Rebecca J.E., Watterson, Mark P., Edwards, Alison A., Ansell, Christopher W.G., Tranter, George E., 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. (doi:10.1016/j.tetasy.2003.12.031) (Access to this publication is currently restricted. You may be able to access a copy if URLs are provided) (KAR id:4886)

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Official URL: 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
DOI/Identification number:	10.1016/j.tetasy.2003.12.031
Subjects:	Q Science Q Science > QD Chemistry
Divisions:	Divisions > Division of Natural Sciences > Medway School of Pharmacy
Depositing User:	Alison Edwards
Date Deposited:	05 Sep 2008 12:56 UTC
Last Modified:	16 Nov 2021 09:43 UTC
Resource URI:	https://kar.kent.ac.uk/id/eprint/4886 (The current URI for this page, for reference purposes)

University of Kent Author Information

Edwards, Alison A..

Creator's ORCID:	https://orcid.org/0000-0002-4637-9373
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