IIIT Hyderabad Publications |
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Electronic structure based study of furan derived peptidesAuthors: N. V. Suresh Kumar,Harjinder Singh,Tushar K Chakraborty Conference: International Symposium, " Of Molecules and Materials (A Survey of Recent Concepts)" (OMAM 2009) Location IISER, Kolkata Date: 2009-12-28 Report no: IIIT/TR/2009/192 AbstractCyclic peptides incorporating a 5 membered ring such as furan mimic naturally occurring cyclic peptides[1]. The preferred conformation of linear and cyclic tripeptides incorporating such sugar amino acids depends on the stereochemistry at the chiral center. Control of stereochemistry at C position of amino ethyl furan carboxylic acid (AEFC) unit in the linear and cyclic tripeptides is investigated using structural parameters and energetics data obtained from density functional theory (DFT) based calculations at B3LYP/6-31G(d,p) level of theory. We found that R-isomer of AEFC unit prefers to form bond with its S-isomer. Thermodynamic analysis revealed that linear tripeptide formed by two R-configured isomers of AEFC and one S-configured isomer of AEFC (RRS or RSR linear) is more stable than that formed by three R-configured isomers of AEFC (RRR linear). It is found that the cyclic tripeptide formed by two R-configured isomers of AEFC and one S-configured isomer of AEFC, i. e., cyclic RRS product is formed with high yield than that formed by three R-configured isomers of AEFC (RRR cyclic) though cyclic RRR trimer is more stable than cyclic RRS trimer. This is substantiated by kinetic control of reactions leading to cyclic tripeptides from linear tripeptides. Using NBO analysis stabilizing interactions in all the linear and cyclic tripeptides are identified. Molecular electrostatic potential (MESP) surfaces of cyclic tripeptides provide insights of intramolecular hydrogen bond interactions. The MESP mapped electron density surfaces have shown the charge distribution around the cyclic peptides. Full paper: pdf Centre for Computational Natural Sciences and Bioinformatics |
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