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

By Benjamin A. Mayes, Rebecca J.E. Stetz, Mark P. Watterson, Alison A. Edwards, Christopher W.G. Ansell, George E. Tranter and George W.J. Fleet


Circular dichroism studies on a series of linear oligomers derived from a protected 6-amino-6-deoxy-D-galactonate (an \ud 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

Topics: Q, QD
Publisher: Elsevier
Year: 2004
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