PMID: 2489104Dec 1, 1989Paper

Structural versatility of peptides containing C alpha, alpha-dialkylated glycines. An X-ray diffraction study of six 1-aminocyclopropane-1-carboxylic acid rich peptides

International Journal of Biological Macromolecules
E BenedettiM Crisma

Abstract

The molecular and crystal structures of six fully blocked, Ac3c-rich peptides to the tetramer level were determined by X-ray diffraction. The peptides are Fmoc-(Ac3c)2-OMe-CH3OH, Ac-(Ac3c)2-OMe, t-Boc-Ac3c-L-Phe-OMe, pBrBz-(Ac3c)3-OMe.H2O, Z-Gly-Ac3c-Gly-OTmb.(CH3)2CO, and t-Boc-(Ac3c)4-OMe.2H2O. Type-I (I') beta-bends and distorted 3(10)-helices were found to be typical of the tri- and tetrapeptides, respectively. In the dipeptides, too short to form beta-bend conformations, other less common structural features may be observed. The average geometry of the cyclopropyl moiety of the Ac3c residue is asymmetric and the N-C alpha-C' bond angle is significantly expanded from the regular tetrahedral value. A comparison with the structural preferences of other extensively investigated C alpha, alpha-dialylated alpha-amino acids is made and the implications for the use of the Ac3c residue in conformational design are examined.

References

Aug 1, 1987·Proceedings of the National Academy of Sciences of the United States of America·I L KarleP Balaram
Feb 1, 1968·Northwest Medicine
Apr 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·A BavosoG M Bonora

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Citations

Feb 25, 2009·The Journal of Organic Chemistry·Guillem Revilla-LópezCarlos Alemán
Feb 3, 2015·Journal of Peptide Science : an Official Publication of the European Peptide Society·Marco CrismaClaudio Toniolo
Dec 29, 2016·Journal of the American Chemical Society·Anthony J MetranoScott J Miller
Mar 11, 2016·Chemical Communications : Chem Comm·A J MetranoS J Miller
Feb 10, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Prema G VasudevNarayanaswamy Shamala
Aug 27, 1999·Journal of Peptide Science : an Official Publication of the European Peptide Society·J Gomez-CatalanC Cativiela
Apr 29, 2004·Journal of Peptide Science : an Official Publication of the European Peptide Society·Saumen DattaN Shamala
Jan 28, 2003·Biopolymers·Cristina PeggionEttore Benedetti
Mar 1, 1994·International Journal of Peptide and Protein Research·J R BailieR F Murphy
Dec 18, 2007·The Journal of Organic Chemistry·Jordi CasanovasCarlos Alemán
Mar 20, 2009·The Journal of Organic Chemistry·Alejandra Flores-OrtegaCarlos Alemán
Jun 25, 2009·Journal of Chemical Information and Modeling·David ZanuyCarlos Alemán
Oct 20, 2006·The Journal of Physical Chemistry. B·Carlos AlemanRuth Nussinov
Dec 15, 2006·Chemical Reviews·Armin de MeijereHeiko Schill
Mar 17, 2006·The Journal of Physical Chemistry. B·Jordi CasanovasCarlos Aleman

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