Preferential polymerization of 5-(aminomethyl)-2-furancarboxylic acid (AMFC) into a cyclic tripeptide

Singh, Harjinder ; Arora, Karunesh ; Tapadar, Subhasish ; Chakraborty, Tushar K. (2004) Preferential polymerization of 5-(aminomethyl)-2-furancarboxylic acid (AMFC) into a cyclic tripeptide Journal of Theoretical and Computational Chemistry, 3 (4). pp. 555-566. ISSN 0219-6336

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Official URL: http://www.worldscinet.com/jtcc/03/0304/S021963360...

Related URL: http://dx.doi.org/10.1142/S0219633604001203

Abstract

Theoretical justification for the preferential formation of an 18-membered cyclic oligopeptide 1 based on 5-(aminomethyl)-2-furancarboxylic acid (AMFC, 2), is attempted using ab initio quantum chemical calculations. The free energy values obtained from Hessian calculations show that while the formation of the higher order cyclized oligopeptides [HN-H2C-(furan)-CO]n with n = 3,4, is energetically favorable, the formation of the cyclic dipeptide 3 is thermodynamically unfavorable. Inclusion of the solvent in calculations enhances this preference further. A plausible explanation for this is the proximity of repulsive charges on the furan O atoms in the dimer 3. Details of geometric parameters and Mulliken charges support this possibility. The repulsion is enhanced, as low frequency modes of nuclear motion that bring these O atoms closer are active at room temperature.

Item Type:Article
Source:Copyright of this article belongs to World Scientific Publishing Co Pte Ltd.
Keywords:Ab Initio; 5-(aminomethyl)-2-furancarboxylic Acid; Free Energy; Onsager Reaction Field Model
ID Code:20559
Deposited On:20 Nov 2010 14:19
Last Modified:22 May 2011 15:08

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