Synthesis of [1, 6-cyclo(Acetyl-1-L-glutamic acid, 2-D-phenylalanine, 3-D-tryptophan, 6-D-lysine)] luteinizing hormone-releasing hormone on poly-N-acrylylpyrrolidine resin
| Autor: | Gerald Skala, John W. Wilks, Clark W. Smith |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Ovulation
chemistry.chemical_classification Gonadotropins Equine Stereochemistry Lysine Acrylic Resins Rats Inbred Strains Peptide Glutamic acid Cleavage (embryo) Biochemistry Rats Gonadotropin-Releasing Hormone chemistry.chemical_compound Tosyl chemistry Amide ring Animals Biological Assay Female Indicators and Reagents Methanol Amino Acids Protecting group |
| Zdroj: | International Journal of Peptide and Protein Research. 21:127-134 |
| ISSN: | 0367-8377 |
| Popis: | The protected peptide, Ac-Glu(OBut)-D-Phe-D-Trp-Ser(But)-Tyr(But)-D-Lys (Z)-Leu-Arg(Tos)-Pro-Gly-NH2 was synthesized in a stepwise manner on a resin of poly-N-acrylylpyrrolidine using both acid cleavable N alpha-tert.-butyloxycarbonyl and base cleavable N alpha-fluorenylmethyloxycarbonyl protecting groups. After cleavage by ammonolysis in methanol, the tert.-butyl and benzyloxy-carbonyl side-chain protecting groups were cleaved with CF3-CO2H-thioanisole and the 1-6 amide ring formed by cyclization with diphenylphosphorylazide, after which the remaining tosyl protecting group was cleaved in HF-anisole. [1,6-Cyclo(Ac-Glu1, D-Phe2, D-Trp3, D-Lys6]LH-RH exhibited less than 10% of the antiovulatory potency of [D less than Glu1, D-Phe2, D-Trp3,6] LH-RH, a potent linear antagonist. |
| Databáze: | OpenAIRE |
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