C - Chemistry – Metallurgy – 07 – K
Patent
C - Chemistry, Metallurgy
07
K
530/7.2
C07K 7/23 (2006.01) C07K 5/103 (2006.01)
Patent
CA 1082172
ABSTRACT OF THE DISCLOSURE A method for preparing (pyro)glutamyl-histidyl-tryptophyl- seryl-tyrosyl-glycyl-leucyl-arginyl-prolyl-glycine amide which comprises reacting an oligopeptide fragment identified as (I) with an oligopeptide fragment identified as (II), each of which are prepared according to the synthesis described below, to form the heptapeptide, seryl-tyroxyl-glycyl-leucyl-arginyl-prolyl-glycine amide having some corresponding protective groups thereon, and coupling the resulting heptapeptide with protected tryptophane, histidine and (pyro)glutamic acid in turn at the nitrogen ter- minal of the each resulting peptide by stepwise elongation to re- sult in a protected decapeptide, and then removing all the pro- tective groups by treating the protected decapeptide with hydrogen fluoride: Fragment (I): Leucyl-(N-protected)arginyl-prolyl-glycineamide is prepared by coupling protected arginine with proline whose carboxyl group is protected, to produce arginyl-proline, coupling glycine amide with the resulted arginyl-proline to produce arginyl-prolyl- glycine amide and further coupling leucine with the .alpha.-nitrogen terminal of the resulting tripeptide and then removing only the protective group on the nitrogen terminal of the leucine portion, and Fragment (II): (N- and O-protected)seryl-(O-protected)tyrosyl-glycine is prepared by coupling a lower alkyl ester of glycine to result in a corresponding seryl-tyrosyl-glycine lower alkyl ester and hydrolyzing only the ester bond of the tripeptide, thus formed.
150746
Kimura Terutoshi
Kumahara Yuichi
Sakakibara Shunpei
Daiichi Pharmaceutical Co. Ltd.
George H. Riches And Associates
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