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Peptides from chiral Cα,α-disubstituted glycines. Synthesis and conformational analysis of homochiral (αMe) Leu / Ala model peptides

✍ Scribed by J. Kamphuis; W. H. J. Boesten; H. E. Schoemaker; A. Aubry; D. Bayeul; A. Dautant; M. Pantano; F. Formaggio; M. Crisma; G. M. Bonora; C. Toniolo

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 635 KB
Volume: 113
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19941130104

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✦ Synopsis

Abstract

Homochiral (αMe)Leu/Ala and Leu/Ala model peptides were synthesized by solution methods and fully characterized. A solution conformational analysis of the tripeptides was carried out using FT‐IR absorption and ^1^H NMR. The crystal‐state structure of Z‐D‐(αMe)Leu‐(D‐Ala)~2~‐OMe monohydrate was resolved by X‐ray diffraction. The results obtained support the conclusion that the tendency of the non‐coded (αMe)Leu residue to fold into β‐bends and helical structures is markedly higher than that of its unmethylated protein counterpart (Leu).

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Keywords: Atropoisomeric amino acids / Axial chirality / C α,α -disubstituted glycine / Crown compounds / Side-chain modified amino acids Racemic and enantiomerically enriched N α -protected methyl 6-amino-1,11-(20-crown-6)-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-6-carboxylates (Boc-[20-C-6]-Bip-OMe