Issue 4, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Comparative conformational analysis of peptides based on the two Cα-tetrasubstituted, Cβ-branched, chiral α-amino acids (αMe)Dip and (αMe)Val†

Yolanda Lapeña,a   Pilar Lopez,a   Carlos Cativiela,a   Bernard Kaptein,b   Quirinus B. Broxterman,b   Johan Kamphuis,c   Eric Mossel,d   Cristina Peggion,d   Fernando Formaggio,d   Marco Crismad  and  Claudio Toniolo‡*d  

* Corresponding authors

a Department of Organic Chemistry, Institute of Materials Science of Aragon, University of Zaragoza-CSIC, Zaragoza, Spain

b DSM Research, Organic Chemistry and Biotechnology Section, PO Box 18, MD Geleen, The Netherlands

c DSM Specialty Intermediates, PO Box 5489, PL Sittard, The Netherlands

d Biopolymer Research Centre, CNR, Department of Organic Chemistry, University of Padova, Padova, Italy

Abstract

For the first time a number of terminally protected model peptides (to the pentamer level) of the sterically demanding α-amino acid Cα-methyl,Cα-diphenylmethylglycine, (αMe)Dip, in combination with either Ala or Gly residues, have been synthesized (by solution methods) and fully characterized. In a parallel synthesis the corresponding peptides based on the related α-amino acid Cα-methyl,Cα-isopropylglycine, (αMe)Val, have also been prepared. The results of a comparative conformational analysis, performed by using FTIR absorption, 1H NMR, and X-ray diffraction techniques, favour the conclusion that, in contrast to the potent β-turn and 310-helix promoter (αMe)Val, (αMe)Dip may induce either a folded or a fully extended conformation. These findings indicate that, despite the common Cα-methylated and Cβ-branched features, (αMe)Dip and (αMe)Val are characterized by partially divergent conformational bias.

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Article information

DOI
https://doi.org/10.1039/A909856I
Article type
Paper
Submitted
15 Dec 1999
Accepted
02 Feb 2000
First published
17 Mar 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 631-636

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Comparative conformational analysis of peptides based on the two Cα-tetrasubstituted, Cβ-branched, chiral α-amino acids (αMe)Dip and (αMe)Val

Y. Lapeña, P. Lopez, C. Cativiela, B. Kaptein, Q. B. Broxterman, J. Kamphuis, E. Mossel, C. Peggion, F. Formaggio, M. Crisma and C. Toniolo, J. Chem. Soc., Perkin Trans. 2, 2000, 631 DOI: 10.1039/A909856I

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