Synthesis, Ion Complexation Study, and 3D-Structural Analysis of Peptides Based on Crown-Carrier, Cα-Methyl-L-DOPA Amino Acids
✍ Scribed by Karen Wright; Rachid Anddad; Jean-François Lohier; Vincent Steinmetz; Michel Wakselman; Jean-Paul Mazaleyrat; Fernando Formaggio; Cristina Peggion; Marta De Zotti; Timothy A. Keiderling; Rong Huang; Claudio Toniolo
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 783 KB
- Volume
- 2008
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
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)