Effect of simple amino acid replacements on the biological activity of luteinizing hormone-releasing hormone

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

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Six decapeptides having structures based on the LH-RH sequence, <Glu-His-Trp-Ser-Tyr-Gly-Leu-Arg- Pro-Gly-NH2, have been synthesized by modifications of the solid-phase technique via protected peptide intermediates. Thus, pyroglutamic acid, tryptophan, serine, glycine, proline, and glycine amide residues in the LH-RH sequence were replaced by leucine, tyrosine, threonine, isoleucine, alanine, and glycine dimethylamide, respectively. The compounds were assayed in vivo and found to possess the following LH-releasing potencies relative to pure, natural LH-RH: [Leu1]-LH-RH, 0.003%; [Tyr3]-LH-RH, 0.13%; [Thr4]-LH-RH, 19%; [Ile6]-LH-RH, 0.034%; [Ala9]-LH-RH, 0.8%; and [(Gly-dimethylamide)10]-LH-RH, 14%.

Original languageEnglish
Pages (from-to)1140-1143
Number of pages4
JournalJournal of Medicinal Chemistry
Volume16
Issue number10
StatePublished - Dec 1 1973
Externally publishedYes

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Bioactivity
Gonadotropin-Releasing Hormone
Amino Acids
Glycine
Pyrrolidonecarboxylic Acid
Isoleucine
Threonine
Proline
Leucine
Tryptophan
Alanine
Serine
Tyrosine
Peptides

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Effect of simple amino acid replacements on the biological activity of luteinizing hormone-releasing hormone. / Coy, David H.; Coy, Esther J.; Schally, Andrew V.

In: Journal of Medicinal Chemistry, Vol. 16, No. 10, 01.12.1973, p. 1140-1143.

Research output: Contribution to journalArticle

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abstract = "Six decapeptides having structures based on the LH-RH sequence, <Glu-His-Trp-Ser-Tyr-Gly-Leu-Arg- Pro-Gly-NH2, have been synthesized by modifications of the solid-phase technique via protected peptide intermediates. Thus, pyroglutamic acid, tryptophan, serine, glycine, proline, and glycine amide residues in the LH-RH sequence were replaced by leucine, tyrosine, threonine, isoleucine, alanine, and glycine dimethylamide, respectively. The compounds were assayed in vivo and found to possess the following LH-releasing potencies relative to pure, natural LH-RH: [Leu1]-LH-RH, 0.003{\%}; [Tyr3]-LH-RH, 0.13{\%}; [Thr4]-LH-RH, 19{\%}; [Ile6]-LH-RH, 0.034{\%}; [Ala9]-LH-RH, 0.8{\%}; and [(Gly-dimethylamide)10]-LH-RH, 14{\%}.",
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N2 - Six decapeptides having structures based on the LH-RH sequence, <Glu-His-Trp-Ser-Tyr-Gly-Leu-Arg- Pro-Gly-NH2, have been synthesized by modifications of the solid-phase technique via protected peptide intermediates. Thus, pyroglutamic acid, tryptophan, serine, glycine, proline, and glycine amide residues in the LH-RH sequence were replaced by leucine, tyrosine, threonine, isoleucine, alanine, and glycine dimethylamide, respectively. The compounds were assayed in vivo and found to possess the following LH-releasing potencies relative to pure, natural LH-RH: [Leu1]-LH-RH, 0.003%; [Tyr3]-LH-RH, 0.13%; [Thr4]-LH-RH, 19%; [Ile6]-LH-RH, 0.034%; [Ala9]-LH-RH, 0.8%; and [(Gly-dimethylamide)10]-LH-RH, 14%.

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