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β‐Peptides: Oligo‐β‐homoalanines – the Amide Analogues of Poly(3‐hydroxybutanoate)
Author(s) -
Matthews Jennifer L.,
Overhand Mark,
Kühnle Florian N. M.,
Ciceri Paola E.,
Seebach Dieter
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970714
Subject(s) - chemistry , amide , lithium amide , lithium (medication) , cyclic peptide , decomposition , peptide , solubility , stereochemistry , nmr spectra database , combinatorial chemistry , organic chemistry , spectral line , catalysis , enantioselective synthesis , medicine , biochemistry , physics , astronomy , endocrinology
Abstract The linear oligo‐β‐peptides derived from β‐homoalanine (Hβ‐HAlaOH) 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.