Isosteres of peptides: boron analogs as dipolar forms of -amino acids - a theoretical study

Malde, Alpeshkumar K., Khedkar, Santosh A. and Coutinho, Evans C. (2007) Isosteres of peptides: boron analogs as dipolar forms of -amino acids - a theoretical study. Journal of Physical Organic Chemistry, 20 2: 151-160. doi:10.1002/poc.1139


Author Malde, Alpeshkumar K.
Khedkar, Santosh A.
Coutinho, Evans C.
Title Isosteres of peptides: boron analogs as dipolar forms of -amino acids - a theoretical study
Journal name Journal of Physical Organic Chemistry   Check publisher's open access policy
ISSN 1099-1395
0894-3230
Publication date 2007-01-01
Sub-type Article (original research)
DOI 10.1002/poc.1139
Volume 20
Issue 2
Start page 151
End page 160
Total pages 10
Place of publication Chichester, England
Publisher Wiley
Language eng
Subject 030701 Quantum Chemistry
Abstract Modification of peptides to produce peptidomimetics is of great interest, with the aim of designing potent, selective, and metabolically stable analogs having certain conformational properties. Organoboranes have been reported in the literature with a wide range of therapeutic applications. One of the therapeutically important class of molecules is amine-carboxyboranes derived from amino acids by replacement of the C atom of an amino acid/peptide by boron. The conformational preferences of these peptides, with respect to backbone , , and torsion angles, have been investigated by theoretical calculations. The amide bond in these molecules has the same geometry in the ground and transition states as the natural peptides. However, the boron isosteres of glycine and alanine peptides are less structured than their natural derivatives, but are distinguished by structures with a positive value for the angle, which is normally disfavored for natural peptides. This property could be used to build peptides with a geometry not usually seen in natural peptides. Copyright © 2007 John Wiley & Sons, Ltd.
Keyword boron isostere of C atom of peptides
ab initio calculations
PES and peptide conformations
Q-Index Code C1

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
School of Chemistry and Molecular Biosciences
 
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