ISSN:
1438-2199
Keywords:
Amino acids
;
LHRH-antagonists
;
Unnatural amino acids
;
Antiovulatory activity
;
Histamine release
;
Solid phase peptide synthesis
Source:
Springer Online Journal Archives 1860-2000
Topics:
Medicine
Notes:
Summary Several LHRH antagonists with trans-3-(4-pyrazinylcarbonylaminocyclohexyl)alanine (trans-PzACAla) in the position 5 were synthesized and their antiovulatory activity was compared with the activity of the analogs containing cis-PzACAla in this position. In all cases cis-isomer produced more potent analogs. Introduction of cis-PzACAla in the position 5 of Antide gave Antide B which completely inhibits ovulation at a dose of 0.5µg/rat. Antide B releases negligible histamine (ED50 = 104µg/mL), and has excellent solubility in water. Also, an improved synthesis of cis-PzACAla is reported, involving the hydrogenation of 4-aminophenylalanine on a rhodium catalyst to give the desired cis-isomer with a 53% yield.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00806547
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