Oxytocin and its analogs, methyl-substituted in ortho-, meta- or para-position of aromatic ring of phenylalanine in position 2: NMR study and biological activities.
Complete analyses of NMR data of oxytocin (OT) and 4 analogues, ([o-MePhe(2)]OT, [mMe-Phe(2)]OT, [m-OMePhe(2)]OT and [p-MePhe(2)]OT), are given. The same conformational behavior in solution on one hand and large differences in biological activities on the other hand indicate that the compounds adopt a "biologically active conformation" at the stage of interaction with the receptor when the character of the substituent and its position on the aromatic ring may play a role in hindering attaining the ideal complementarity of both interacting components.
Budesínsky
Milos
M
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague.
Procházka
Zdenko
Z
Slaninová
Jirina
J
D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010121:Oxytocin / Q000031:analogs & derivatives / Q000037:antagonists & inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D010649:Phenylalanine / Q000737:chemistry*; D013329:Structure-Activity Relationship
D010649:Phenylalanine; D010121:Oxytocin