Stereoisomers of luteinizing hormone-releasing hormone

Yoshihiro Hirotsu; David H. Coy; Esther J. Coy; Andrew V. Schally

doi:10.1016/S0006-291X(74)80203-2

Stereoisomers of luteinizing hormone-releasing hormone

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

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Abstract

Six decapeptide analogs of the luteinizing hormone-releasing hormone (LH-RH) were prepared with the D-isomers of pyroglutamic acid, histidine, tryptophan, tyrosine, leucine, and arginine successively replacing the corresponding L-amino acids of the hormone. [D-pGlu¹]-LH-RH and [D-His²]-LH-RH had appreciable LH-releasing activities, 8% and 9%, respectively. The remaining analogs were less potent, having the following activities: [D-Trp³]-LH-RH, 0.1%; [D-Tyr⁵]-LH-RH, 0.1%; [D-Leu⁷]-LH-RH, 1.0%; [D-Arg⁸]-LH-RH, 0.3%.

Original language	English (US)
Pages (from-to)	277-282
Number of pages	6
Journal	Biochemical and biophysical research communications
Volume	59
Issue number	1
DOIs	https://doi.org/10.1016/S0006-291X(74)80203-2
State	Published - Jul 10 1974

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ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology
Cell Biology

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Hirotsu, Y., Coy, D. H., Coy, E. J., & Schally, A. V. (1974). Stereoisomers of luteinizing hormone-releasing hormone. Biochemical and biophysical research communications, 59(1), 277-282. https://doi.org/10.1016/S0006-291X(74)80203-2

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abstract = "Six decapeptide analogs of the luteinizing hormone-releasing hormone (LH-RH) were prepared with the D-isomers of pyroglutamic acid, histidine, tryptophan, tyrosine, leucine, and arginine successively replacing the corresponding L-amino acids of the hormone. [D-pGlu1]-LH-RH and [D-His2]-LH-RH had appreciable LH-releasing activities, 8% and 9%, respectively. The remaining analogs were less potent, having the following activities: [D-Trp3]-LH-RH, 0.1%; [D-Tyr5]-LH-RH, 0.1%; [D-Leu7]-LH-RH, 1.0%; [D-Arg8]-LH-RH, 0.3%.",

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AB - Six decapeptide analogs of the luteinizing hormone-releasing hormone (LH-RH) were prepared with the D-isomers of pyroglutamic acid, histidine, tryptophan, tyrosine, leucine, and arginine successively replacing the corresponding L-amino acids of the hormone. [D-pGlu1]-LH-RH and [D-His2]-LH-RH had appreciable LH-releasing activities, 8% and 9%, respectively. The remaining analogs were less potent, having the following activities: [D-Trp3]-LH-RH, 0.1%; [D-Tyr5]-LH-RH, 0.1%; [D-Leu7]-LH-RH, 1.0%; [D-Arg8]-LH-RH, 0.3%.

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10.1016/S0006-291X(74)80203-2