Synthesis, biological activity, and tritiation of L-3, 4-dehydroproline-containing peptides.
A series of analogs of thyroliberin (TRH) ([L-delta3Pro3]-TRH, [D-delta3Pro3]-TRH, [L-3-MeHis2, L-delta3Pro3]-TRH) in which proline was replaced by L- or D-3, 4-dehydroproline was synthesized. The analogs exhibited approximately the same biological activity as the corresponding proline-containing peptides. These analogs and others in which 3, 4-dehydroproline is present at the NH2-terminal, COOH-terminal or internal positions in the peptide were successfully reduced with deuterium or tritium to provide the 3, 4-2H2-proline or 3,4-3H2-proline analogs, respectively, with near theoretical values of substitution. A novel procedure for the chemical resolution of DL-3, 4-dehydroproline is also described.
D000818:Animals; D002478:Cells, Cultured; D055598:Chemical Phenomena; D002621:Chemistry; D003903:Deuterium; D066298:In Vitro Techniques; D010455:Peptides / Q000138:chemical synthesis / Q000494:pharmacology; D011392:Proline / Q000031:analogs & derivatives / Q000378:metabolism; D051381:Rats; D013972:Thyrotropin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000378:metabolism; D014316:Tritium
D010455:Peptides; D014316:Tritium; D013972:Thyrotropin; D011392:Proline; D003903:Deuterium