Stereochemical studies on cyclic peptides

Ramakrishnan, C. ; Narasinga Rao, B. N. (1980) Stereochemical studies on cyclic peptides International Journal of Peptide and Protein Research, 15 (2). pp. 81-95. ISSN 0367-8377

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Conformational analysis of cyclic pentapeptides having two intra-ring 3 1 hydrogen bonds has been carried out. It is found that the structure can easily be formed with trans planar peptide units without causing significant angular strain at the α-carbon atoms. Four different types of conformations designated Types I-IV are possible for the backbone structure. Details of these four types of conformations and also the accommodating possibility of these types for all-glycyl and all-alanyl residues are presented. Three of the four types have relatively low energies for glycyl residues whereas the other one has a slightly higher energy. When alanyl residues are introduced at the five α-carbon atoms, the types that are energetically favourable depend upon the sequence of isomers. Energy calculations have also been carried out for the combinations of glycyl, L- and D-alanyl residues. The theoretical results are compared with available experimental observations both from solution and solid state studies.

Item Type:Article
Source:Copyright of this article belongs to Munksgaard International Publishers.
Keywords:Conformation; Cyclic Pentapeptide; 3 1 Hydrogen Bond (in Cyclic Pentapeptide); Pentapeptide-cyclic; Ring Closure in Cyclic Pentapeptide; Stereochemistry
ID Code:41012
Deposited On:26 May 2011 06:03
Last Modified:26 May 2011 06:03

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