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Oostatic peptides containing d-amino acids: synthesis, oostatic activity, degradation, accumulation in ovaries and NMR study
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SYSNO ASEP 0376950 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Oostatic peptides containing d-amino acids: synthesis, oostatic activity, degradation, accumulation in ovaries and NMR study Author(s) Hlaváček, Jan (UOCHB-X)
Tykva, Richard (UOCHB-X)
Holík, Josef (UEB-Q) RID, ORCID
Bennettová, Blanka (BC-A)
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Vlasáková, Věra (UEB-Q)
Černý, Bohuslav (UEB-Q) RID
Slaninová, Jiřina (UOCHB-X)Number of authors 8 Source Title Amino Acids. - : Springer - ISSN 0939-4451
Roč. 42, č. 5 (2012), s. 1715-1725Number of pages 11 s. Language eng - English Country AT - Austria 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 R&D Projects GA203/06/1272 GA ČR - Czech Science Foundation (CSF) CEZ AV0Z40550506 - UOCHB-X (2005-2011) AV0Z50380511 - UEB-Q (2005-2011) AV0Z50070508 - ENTU-I, BC-A (2005-2011) UT WOS 000302812700017 DOI 10.1007/s00726-011-0882-6 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2013
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