Conformationally biased analogs of oxytocin.
Four diastereomeric analogs of oxytocin containing substituted phenylalanine in position 2 were synthesized. This modified phenylalanine side chain contained one methyl group attached to the beta-carbon and the second one at the 2' position of the aromatic ring. All analogs were found to be inhibitors of uterotonic activity of oxytocin with pA2 values ranging from 6.0 to 8.3; the most potent one (pA2 = 8.3) contained dimethylphenylalanine of the D-erythro configuration.
Lebl
M
M
Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, Prague.
Toth
G
G
Slaninová
J
J
Hruby
V J
VJ
D000595:Amino Acid Sequence; D000818:Animals; D005260:Female; D066298:In Vitro Techniques; D008969:Molecular Sequence Data; D010120:Oxytocics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010121:Oxytocin / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D010649:Phenylalanine / Q000737:chemistry; D011487:Protein Conformation; D051381:Rats; D013237:Stereoisomerism; D014590:Uterine Contraction / Q000187:drug effects; D014599:Uterus / Q000187:drug effects
D010120:Oxytocics; C078366:oxytocin, 3,2'-di-Me-Phe(2)-; D010649:Phenylalanine; D010121:Oxytocin