Abstract
The protected decapeptides pyroglutamyl-N im-benzylhistidyltryptophyl-O-benzylseryl-O-methyltyrosyl- glycylleucyl-NG-tosylarginylprolylglycine amide and pyroglutamylhistidyltryptophyl-O-benzylseryl-p nitrophenylalanylglycylleucyl-NG-tosylarginylprolylglycine amide were synthesized by solid-phase methods. They were converted to [5-(p-methoxyphenylalanine)]-LH-RH and [5-(p-nitrophenylalanine)]-LH-RH by reaction with sodium in liquid ammonia and anhydrous hydrogen fluoride, respectively Treatment of the p-nitrophenylalanine-protected peptide with sodium in liquid ammonia resulted in both the reduction of the nitro group to an amino group and the removal of the protecting groups to give [5-(p-aminophenylalanine)]-LH-RH in good yield. These analogs were assayed in vivo against pure natural LH-RH and found to possess the following LH-releasing activities: [5-(p-aminophenylalanine)]-LH-RH, 37%; [5-(p-methoxyphenylalanine)]-LH-RH, 24%; [5-(p-nitrophenylalanine)]-LH-RH, 5%.
Original language | English (US) |
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Pages (from-to) | 827-829 |
Number of pages | 3 |
Journal | Journal of Medicinal Chemistry |
Volume | 16 |
Issue number | 7 |
DOIs | |
State | Published - Jul 1 1973 |
Externally published | Yes |
ASJC Scopus subject areas
- Molecular Medicine
- Drug Discovery