β‐Peptides: Oligo‐β‐homoalanines – the Amide Analogues of Poly(3‐hydroxybutanoate)

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Abstract
The linear oligo‐β‐peptides derived from β‐homoalanine (Hβ‐HAlaOH) have been prepared by Arndt‐Eistert homologation of Boc‐alanine and subsequent peptide coupling procedures. Cyclisation via pentafluorophenyl esters resulted in the formation of the cyclic β‐peptides in remarkably high yields. The X‐ray crystal structure analysis of Boc–(β‐HAla)2–OBn is presented. The cyclic derivatives were found to be highly insoluble (m.p. >300°C with decomposition) and the effect of lithium salts on their solubility, particularly with respect to obtaining NMR data, is discussed. The CD spectra of the cyclo‐β‐tetrapeptides are presented and these give an indication that “nanotube‐like” structures may be present.

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