PMID: 591179Oct 1, 1977

Synthesis, biological activity, and tritiation of L-3, 4-dehydroproline-containing peptides

International Journal of Peptide and Protein Research
A M FelixJ Meienhofer

Abstract

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.

References

Jan 1, 1975·International Journal of Peptide and Protein Research·A M FelixM R Cohen
Jun 18, 1971·Biochemical and Biophysical Research Communications·R M NairA V Schally
Jan 1, 1973·Archives of Biochemistry and Biophysics·J O McGeeS Udenfriend
Jan 1, 1973·International Journal of Peptide and Protein Research·A M FelixM R Cohen
Jan 1, 1970·Helvetica Chimica Acta·D GillessenR O Studer
Jul 1, 1971·Proceedings of the National Academy of Sciences of the United States of America·M E CelisR Walter
Jan 1, 1967·Justus Liebigs Annalen der Chemie·E Schnabel

Related Concepts

Deuterons
Polypeptides
Proline
Thyrotropin
Tritium

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