Premium
Synthesis, Ion Complexation Study, and 3D‐Structural Analysis of Peptides Based on Crown‐Carrier, C α ‐Methyl‐ L ‐DOPA Amino Acids
Author(s) -
Wright Karen,
Anddad Rachid,
Lohier JeanFrançois,
Steinmetz Vincent,
Wakselman Michel,
Mazaleyrat JeanPaul,
Formaggio Fernando,
Peggion Cristina,
De Zotti Marta,
Keiderling Timothy A.,
Huang Rong,
Toniolo Claudio
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700917
Subject(s) - chemistry , random hexamer , amino acid , crown ether , stereochemistry , alkali metal , peptide , ion , organic chemistry , crystallography , biochemistry
Abstract Selected series of terminally protected model peptides to the hexamer level, based on four novel, crown‐ether containing C α ‐methyl‐ L ‐DOPA ( L ‐Mdp) amino acid residues, namely L ‐Mdp[15‐C‐5], L ‐Mdp[18‐C‐6], L ‐Mdp[benzo‐24‐C‐8] and L ‐Mdp[( S )‐Binol‐20‐C‐6], combined with either L ‐Ala or L ‐Ala/Aib or Gly/Aib, were synthesized by solution methods. An ESI‐MS analysis of their alkali metal cation complexation ability was carried out. Their FTIR absorption, 1 H NMR, ECD, and VCD spectroscopic properties suggest that all of these crowned amino acids are strong inducers of (left‐handed) β‐turns and 3 10 ‐helical structures.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)