Local control of peptide conformation: stabilization of cis proline peptide bonds by aromatic proline interactions

Biopolymers
W J Wu, D P Raleigh

Abstract

In the native state of proteins there is a marked tendency for an aromatic amino acid to precede a cis proline. There are also significant differences between the three aromatic amino acids with Tyr exhibiting a noticeably higher propensity than Phe or Trp to precede a cis proline residue. In order to study the role that local interactions play in these conformation preferences, a set of tetrapeptides of the general sequence acetyl-Gly-X-Pro-Gly-carboxamide (GXPG), where X = Tyr, Phe, Trp, Ala, or cyclohexyl alanine, were synthesized and studied by nmr. Analysis of the nmr data shows that none of the peptides adopt a specific backbone structure. Ring current shifts, the equilibrium constant, the Van't Hoff enthalpy, and the measured rate of cis-trans isomerization all indicate that the cis proline conformer is stabilized by favorable interactions between the aromatic ring and the proline residue. Analysis of the side chain conformation of the aromatic residue and analysis of the chemical shifts of the pyrrolidine ring protons shows that the aromatic side chain adopts a preferred conformation in the cis form. The distribution of rotamers and the effect of an aromatic residue on the cis-trans equilibrium indicate that the preferr...Continue Reading

References

Oct 1, 1978·Proceedings of the National Academy of Sciences of the United States of America·F X Schmid, R L Baldwin
Oct 1, 1992·Proceedings of the National Academy of Sciences of the United States of America·K P WilsonB W Matthews
Jan 1, 1991·Annual Review of Biophysics and Biophysical Chemistry·H J Dyson, P E Wright
Mar 20, 1991·Journal of Molecular Biology·M W MacArthur, J M Thornton
Jul 5, 1990·Journal of Molecular Biology·D E StewartJ E Wampler
May 5, 1988·Journal of Molecular Biology·H J DysonR A Lerner
Feb 2, 1971·Biochemistry·J E Brown, W A Klee
Jan 20, 1995·Journal of Molecular Biology·J Kemmink, T E Creighton
Jun 1, 1995·Biophysical Chemistry·R L Baldwin
Mar 1, 1993·Proceedings of the National Academy of Sciences of the United States of America·K A DillH S Chan
Dec 1, 1994·Protein Science : a Publication of the Protein Society·E G Hutchinson, J M Thornton
Nov 4, 1994·Journal of Molecular Biology·J YaoH J Dyson
Jan 1, 1993·Advances in Protein Chemistry·F X SchmidE R Schönbrunner
Jan 1, 1996·Folding & Design·Z K Feng, M J Sippl
Jun 1, 1997·Protein Science : a Publication of the Protein Society·P A Karplus
May 7, 1993·Tetrahedron Letters·Eric S EberhardtRonald T Raines

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Citations

Sep 24, 2008·BMC Structural Biology·Bhaskar Dasgupta, Pinak Chakrabarti
Jan 10, 2012·Amino Acids·Agnel Praveen JosephAlexandre G de Brevern
Sep 4, 2007·FEBS Letters·Bhaskar DasguptaGautam Basu
Dec 8, 2015·The Journal of Physical Chemistry. B·Yu-Ju LinJia-Cherng Horng
Mar 30, 2001·Journal of Peptide Science : an Official Publication of the European Peptide Society·L Halab, W D Lubell
Sep 6, 2002·Journal of Peptide Science : an Official Publication of the European Peptide Society·Assunta NapolitanoRaffaele Riccio
Sep 24, 2015·Proceedings of the National Academy of Sciences of the United States of America·Hee Jung KimHyung Ho Lee
Nov 18, 2015·Journal of Chemical Theory and Computation·Arghya BarmanDonald Hamelberg
Jul 17, 2007·Progress in Biophysics and Molecular Biology·Pinak Chakrabarti, Rajasri Bhattacharyya
May 21, 2008·Chemistry : a European Journal·Bhaswati ChatterjeePadmanabhan Balaram
Dec 5, 2012·Journal of Peptide Science : an Official Publication of the European Peptide Society·Atul Rawat, Dinesh Kumar
Dec 3, 2014·Peptides·Isabel C M FensterseiferOctavio L Franco
Jun 17, 2014·Biochimica Et Biophysica Acta·Matthias J Feige, Johannes Buchner
Dec 14, 2007·Journal of Proteome Research·Brent Wathen, Zongchao Jia
Nov 15, 2012·Accounts of Chemical Research·Neal J Zondlo
Apr 10, 2010·Journal of the American Chemical Society·Patrick FarberAnthony Mittermaier
Nov 7, 2003·Organic Letters·Carol M TaylorJae H Park
Sep 2, 2016·The Journal of Physical Chemistry. B·Shenlin WangVladimir Ladizhansky
Mar 21, 2007·Molecular BioSystems·David J Craik, Norelle L Daly
Feb 27, 2019·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Shuhui YuZe Zhang
Jun 4, 2013·Amino Acids·Pierrick CraveurJoseph Rebehmed

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