Conformational properties of the residues connected by ester and methylated amide bonds: theoretical and solid state conformational studies

Journal of Peptide Science : an Official Publication of the European Peptide Society
Dawid Siodłak, Anna Janicki

Abstract

Peptides produced by bacteria and fungi often contain an ester bond in the main chain. Some of them have both an ester and methylated amide bond at the same residue. A broad spectrum of biological activities makes these depsipeptides potential drug precursors. To investigate the conformational properties of such modified residues, a systematic theoretical analysis was performed on N-acetyl-L-alanine N'-methylamide (Ac-Ala-NHMe) and the analogues with the ester bond on the C-terminus (Ac-Ala-OMe), N-terminus (Ac-[psi](COO)-Ala-NHMe) as well as the analogues methylated on the N-terminus (Ac-(Me)Ala-OMe) and C-terminus (Ac-[psi](COO)-Ala-NMe(2)). The phi, psi potential energy surfaces and the conformers localised were calculated at the B3LYP/6-311++G(d,p) level of theory both in vacuo and with inclusion of the solvent (chloroform, water) effect (SCRF method). The solid state conformations of the studied residues drawn from The Cambridge Structural Database have been also analysed. The residues with a C-terminal ester bond prefer the conformations beta, C5, and alpha(R), whereas those with N-terminal ester bond prefer the conformations beta, alpha(R), and the unique conformation alpha' (phi, psi = -146 degrees , -12 degrees ). The ...Continue Reading

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Citations

Aug 2, 2011·Journal of Peptide Science : an Official Publication of the European Peptide Society·Dawid SiodłakMałgorzata A Broda
Jul 21, 2010·Journal of Peptide Science : an Official Publication of the European Peptide Society·Dawid SiodłakBarbara Rzeszotarska
Jun 14, 2017·Journal of Peptide Science : an Official Publication of the European Peptide Society·Anna Kusakiewicz-DawidDawid Siodłak
Mar 14, 2013·The Journal of Physical Chemistry. a·Juhyon J LeeMarkus Gerhards
Feb 18, 2014·The Journal of Physical Chemistry. B·Dawid SiodłakTadeusz Lis
May 28, 2013·Journal of the American Chemical Society·Jonas N N EildalPer Jemth

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