Analogs of luteinizing hormone-releasing hormone containing derivatives of phenylalanine in place of tyrosine

David H. Coy, Esther J. Coy, Andrew V Schally

Research output: Contribution to journalArticle

23 Citations (Scopus)

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 languageEnglish
Pages (from-to)827-829
Number of pages3
JournalJournal of Medicinal Chemistry
Volume16
Issue number7
StatePublished - Dec 1 1973
Externally publishedYes

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Phenylalanine
Gonadotropin-Releasing Hormone
Tyrosine
Derivatives
Ammonia
Amides
Sodium
Hydrofluoric Acid
Liquids
Peptides
4-nitrophenylalanine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Analogs of luteinizing hormone-releasing hormone containing derivatives of phenylalanine in place of tyrosine. / Coy, David H.; Coy, Esther J.; Schally, Andrew V.

In: Journal of Medicinal Chemistry, Vol. 16, No. 7, 01.12.1973, p. 827-829.

Research output: Contribution to journalArticle

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