PMID: 11906604Mar 22, 2002Paper

Determination of stereochemistry stability coefficients of amino acid side-chains in an amphipathic alpha-helix

The Journal of Peptide Research : Official Journal of the American Peptide Society
Y ChenRobert S Hodges

Abstract

We describe here a systematic study to determine the effect on secondary structure of d-amino acid substitutions in the nonpolar face of an amphipathic alpha-helical peptide. The helix-destabilizing ability of 19 d-amino acid residues in an amphipathic alpha-helical model peptide was evaluated by reversed-phase HPLC and CD spectroscopy. l-Amino acid and d-amino acid residues show a wide range of helix-destabilizing effects relative to Gly, as evidenced in melting temperatures (DeltaTm) ranging from -8.5 degrees C to 30.5 degrees C for the l-amino acids and -9.5 degrees C to 9.0 degrees C for the d-amino acids. Helix stereochemistry stability coefficients defined as the difference in Tm values for the l- and d-amino acid substitutions [(DeltaTm' = TmL and TmD)] ranging from 1 degrees C to 34.5 degrees C. HPLC retention times [DeltatR(XL-XD)] also had values ranging from -0.52 to 7.31 min at pH 7.0. The helix-destabilizing ability of a specific d-amino acid is highly dependent on its side-chain, with no clear relationship to the helical propensity of its corresponding l-enantiomers. In both CD and reversed-phase HPLC studies, d-amino acids with beta-branched side-chains destabilize alpha-helical structure to the greatest extent. ...Continue Reading

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Citations

Jan 29, 2005·The Journal of Biological Chemistry·Yuxin ChenRobert S Hodges
Dec 13, 2006·Antimicrobial Agents and Chemotherapy·Yuxin ChenRobert S Hodges
Jul 28, 2012·International Journal of Molecular Sciences·Yi-Bing HuangYu-Xin Chen
Aug 16, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Guirong LiYuxin Chen
May 9, 2014·Protein & Cell·Yibing HuangYuxin Chen
Sep 12, 2015·Materials Science & Engineering. C, Materials for Biological Applications·Punitha VelmuruganAruna Dhathathreyan
Feb 11, 2003·Proteins·John B O Mitchell, James Smith
Dec 19, 2008·Chemical Biology & Drug Design·Ziqing JiangRobert S Hodges
Aug 2, 2011·Chemical Biology & Drug Design·Gui-Rong LiYu-Xin Chen
Apr 29, 2014·Chemical Biology & Drug Design·Adrienne Nyango-Nkeh Leussa, Marina Rautenbach
Oct 4, 2015·Tumour Biology : the Journal of the International Society for Oncodevelopmental Biology and Medicine·Joon Ha LeeJae Sam Hwang
Apr 28, 2005·Analytical and Bioanalytical Chemistry·Christoph Czerwenka, Wolfgang Lindner
May 27, 2017·Chemical Biology & Drug Design·Urszula PiotrowskaEwa Oledzka
Dec 28, 2017·International Journal of Molecular Sciences·Shiyu SunYuxin Chen
Nov 13, 2003·Chembiochem : a European Journal of Chemical Biology·Sergii AfoninAnne S Ulrich
Mar 23, 2011·Journal of Peptide Science : an Official Publication of the European Peptide Society·Qing-Quan MaXing-Jun Feng
Jul 16, 2008·Chemical Biology & Drug Design·Angeliki BukuJoseph A Price
Jul 14, 2009·Journal of Computer-aided Molecular Design·Austin B YongyeKarina Martínez-Mayorga
Feb 24, 2006·Chemical Biology & Drug Design·Yuxin ChenRobert S Hodges
Aug 1, 2008·Journal of Separation Science·Colin T Mant, Robert S Hodges
May 9, 2013·Physical Chemistry Chemical Physics : PCCP·Parvesh WadhwaniAnne S Ulrich
Mar 1, 2012·Organic & Biomolecular Chemistry·Siddappa ChandrappaPadmanabhan Balaram
Jan 8, 2004·Experimental Biology and Medicine·Andrea T BorchersM Eric Gershwin
Jul 7, 2009·Angewandte Chemie·Anna F A PeacockVincent L Pecoraro
Nov 28, 2019·Journal of Medicinal Chemistry·Joseph ChabenneRichard D DiMarchi
Jul 21, 2006·The Journal of Physical Chemistry. B·Rajagopalan Sudha, Martin F Jarrold

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