Oostatic peptides containing d-amino acids: synthesis, oostatic activity, degradation, accumulation in ovaries and NMR study

0376950 - ÚOCHB 2013 RIV AT eng J - Journal Article
Hlaváček, Jan - Tykva, Richard - Holík, Josef - Bennettová, Blanka - Buděšínský, Miloš - Vlasáková, Věra - Černý, Bohuslav - Slaninová, Jiřina
Oostatic peptides containing d-amino acids: synthesis, oostatic activity, degradation, accumulation in ovaries and NMR study.
Amino Acids. Roč. 42, č. 5 (2012), s. 1715-1725. ISSN 0939-4451. E-ISSN 1438-2199
R&D Projects: GA ČR GA203/06/1272
Institutional research plan: CEZ:AV0Z40550506; CEZ:AV0Z50380511; CEZ:AV0Z50070508
Keywords : D-amino acids * oostatic peptide synthesis * H-3 labeling * oostatic activity in Neobellieria bullata * H-3 incorporation * Peptide degradation * NMR study
Subject RIV: CC - Organic Chemistry
Impact factor: 3.914, year: 2012

Analogs of the H-Tyr-Asp-Pro-Ala-Pro-OH pentapeptide with d-amino acid residues either in differing or in all of the positions of the sequences were prepared and their oostatic potency was compared with that of the parent pentapeptide. The d-amino acid residue containing analogs exhibited an equal or even higher oostatic effect in the flesh fly Neobellieria bullata than the parent peptide. Contrary to the rapid incorporation of radioactivity from the labeled H-Tyr-Asp-[H-3]Pro-Ala-Pro-OH pentapeptide into the ovaries of N. bullata in vitro, the radioactivity incorporation from the labeled pentapeptides with either d-aspartic acid or d-alanine was significantly delayed. As compared to the parent pentapeptide, also the degradation of both the d-amino acid-containing analogs mentioned above proceeded at a significantly lower rate. The decreased intake of radioactivity, the lower degradation and finally also the high oostatic effect may be ascribed to the decreased enzymatic degradation of the peptide bonds neighboring the d-amino acid residues in the corresponding peptides. The introduction of the non-coded d-amino acids thus enhances the oostatic effect in N. bullata owing to the prolonged half-life of the corresponding pentapeptides, which can thus affect more ovarian cells.
Permanent Link: http://hdl.handle.net/11104/0209228