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

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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)

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.
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