𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Preferred solution conformation of peptides rich in the lipophilic, chiral, Cα-methylated α-amino acid (αMe)Aoc

✍ Scribed by Cristina Peggion; Fernando Formaggio; Marco Crisma; Claudio Toniolo; Bernard Kaptein; Quirinus B. Broxterman; Johan Kamphuis

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
136 KB
Volume
5
Category
Article
ISSN
1075-2617

No coin nor oath required. For personal study only.

✦ Synopsis

The lipophilic, chiral, C h -methylated h-amino acid L-(h Me)Aoc (2-methyl-2-amino-octanoic acid) was prepared using a chemo-enzymatic approach. Two series of terminally protected model peptides, from dimer through to hexamer, containing L-(h Me)Aoc in combination with either Gly or Aib, were synthesized by solution methods and were fully characterized. A solution conformational analysis, based on FT-IR absorption, 1 H-NMR and circular dichroism (CD) techniques, was performed with the aim at determining the preferred conformation of this novel amino acid and the relationship between chirality at its h-carbon atom and screw sense of the helix that is formed. The results obtained strongly support the view that L-(h Me)Aoc favours the formation of the right-handed 3 10 -helical conformation.

📜 SIMILAR VOLUMES

Effect of phenyl ring position in the Cα
Effect of phenyl ring position in the Cα-methylated α-amino acid side chain on peptide preferred conformation
✍ C. Toniolo; M. Crisma; F. Formaggio; A. Polese; M. Doi; T. Ishida; E. Mossel; Q. 📂 Article 📅 1996 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 308 KB 👁 1 views

The preferred conformations of C"-methyl phenylglycine, C"-methyl phenylalanine, and C"-methyl homophenylalanine residues, as determined in model peptides (including homopeptides) by Fourier transform ir absorption, 'H-nmr, CD, and x-ray diffraction techniques, are compared with the aim of investiga

Conformational characterization of pepti
Conformational characterization of peptides rich in the cycloaliphatic Cα,α-disubstituted glycine 1-amino-cyclononane-1-carboxylic acid
✍ Maddalena Gatos; Fernando Formaggio; Marco Crisma; Giovanni Valle; Claudio Tonio 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 376 KB

A series of N-and C-protected, monodispersed homo-oligopeptides (to the pentamer level) from the cycloaliphatic C Y -dialkylated glycine 1-aminocyclononane-1-carboxylic acid (Ac W c) and two Ala/Ac W c tripeptides have been synthesized by solution methods and fully characterized. The conformational