Synthesis and biological evaluation of LH and FSH releasing hormone and its analogs

Noboru Yanaihara, Chizuko Yanaihara, Masanori Sakagami, Kazuyasu Tsuji, Tadashi Hashimoto, Toshio Kaneko, Hiroshi Oka, Andrew V Schally, Akira Arimura, Tommie W. Redding

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Details and additional information about another synthesis of LH-RH/FSH-RH, pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2 (I), are described. In order to obtain enough highly purified material, the synthesis was performed by stepwise elongation according to the conventional method for peptide synthesis. The product was purified effectively by column chromatography on CM-Sephadex C-25. Homogeneity of the purified product was confirmed by tlc as well as by elementary analysis and acid and enzyme hydrolyses. The in vivo and in vitro activities of the synthetic LH-RH/FSH-RH (I) were of the same order of magnitude as those of pure natural LH-RH/FSH-RH. On the other hand, nonapeptide amide, des-pGlu1-LH-RH/FSH-RH (II), and octapeptide amide, des-pGlu1-des-His2-LH-RH/FSH-RH (III), were, at best, only very weakly active. In addition, I stimulated cyclic AMP formation in rat anterior pituitary, while II and III exhibited no stimulation.

Original languageEnglish
Pages (from-to)373-377
Number of pages5
JournalJournal of Medicinal Chemistry
Volume16
Issue number4
StatePublished - Dec 1 1973
Externally publishedYes

Fingerprint

Gonadotropin-Releasing Hormone
Amides
Synthetic Chemistry Techniques
Column chromatography
Cyclic AMP
Chromatography
Rats
Elongation
Hydrolysis
Peptides
Acids
Enzymes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Yanaihara, N., Yanaihara, C., Sakagami, M., Tsuji, K., Hashimoto, T., Kaneko, T., ... Redding, T. W. (1973). Synthesis and biological evaluation of LH and FSH releasing hormone and its analogs. Journal of Medicinal Chemistry, 16(4), 373-377.

Synthesis and biological evaluation of LH and FSH releasing hormone and its analogs. / Yanaihara, Noboru; Yanaihara, Chizuko; Sakagami, Masanori; Tsuji, Kazuyasu; Hashimoto, Tadashi; Kaneko, Toshio; Oka, Hiroshi; Schally, Andrew V; Arimura, Akira; Redding, Tommie W.

In: Journal of Medicinal Chemistry, Vol. 16, No. 4, 01.12.1973, p. 373-377.

Research output: Contribution to journalArticle

Yanaihara, N, Yanaihara, C, Sakagami, M, Tsuji, K, Hashimoto, T, Kaneko, T, Oka, H, Schally, AV, Arimura, A & Redding, TW 1973, 'Synthesis and biological evaluation of LH and FSH releasing hormone and its analogs', Journal of Medicinal Chemistry, vol. 16, no. 4, pp. 373-377.
Yanaihara N, Yanaihara C, Sakagami M, Tsuji K, Hashimoto T, Kaneko T et al. Synthesis and biological evaluation of LH and FSH releasing hormone and its analogs. Journal of Medicinal Chemistry. 1973 Dec 1;16(4):373-377.
Yanaihara, Noboru ; Yanaihara, Chizuko ; Sakagami, Masanori ; Tsuji, Kazuyasu ; Hashimoto, Tadashi ; Kaneko, Toshio ; Oka, Hiroshi ; Schally, Andrew V ; Arimura, Akira ; Redding, Tommie W. / Synthesis and biological evaluation of LH and FSH releasing hormone and its analogs. In: Journal of Medicinal Chemistry. 1973 ; Vol. 16, No. 4. pp. 373-377.
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