The influence of modification at position 2 on the side-chain conformation in oxytocin analogs. | Zendy

Bogusław Śmiech | Zendy; Rajmund Kaźmierkiewicz | Zendy; Bernard Lammek | Zendy

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The influence of modification at position 2 on the side-chain conformation in oxytocin analogs.

Author(s) -

Bogusław Śmiech,

Rajmund Kaźmierkiewicz,

Bernard Lammek

Publication year - 2006

Publication title -

acta biochimica polonica

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.452

H-Index - 78

eISSN - 1734-154X

pISSN - 0001-527X

DOI - 10.18388/abp.2006_3369

Subject(s) - oxytocin , side chain , phenylalanine , chemistry , lactation , stereochemistry , amino acid , endocrinology , biochemistry , pregnancy , biology , organic chemistry , genetics , polymer

The nonapeptide oxytocin (OT) is used in medicine to help begin and/or continue childbirth. Its analogs can be also used to control bleeding following fetus delivery. The main function of oxytocin is to stimulate contraction of uterus smooth muscle and the smooth muscle of mammary glands, thus regulating lactation. This paper describes theoretical simulations of the distribution of the torsional angles chi1 in the non-standard methylated phenylalanine residues of three oxytocin analogs: [(Phe)(2)o-Me]OT, [(Phe)(2)m-Me]OT, [(Phe)(2)p-Me]OT. The conformations of the oxytocin analogs were studied both in vacuum and in solution. We found some correlations between the biological activity of the considered peptides and the side-chain conformations of amino-acid residues 2 and 8.

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