Solid phase synthesis and biological activities of [Arg8]-vasopressin methylenedithioether.
Solid phase synthesis of [Arg8]-vasopressin methylenedithioether, an analog of vasopressin which contains an extra methylene group between the two sulfur atoms of Cys1 and Cys6, is described. Methylene insertion occurred easily when the thiol free peptide on a solid support was treated with tetrabutylammonium fluoride in dichloromethane at room temperature for 3 h. The uterotonic in vitro, pressor, and antidiuretic activities of the compound were reduced in comparison to [Arg8]-vasopressin by one order of magnitude.
Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Japan.
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M
Ueki
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Ikeo
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Iwadate
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Asakura
M P
MP
Williamson
J
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Slaninová
D000818:Animals; D001127:Arginine Vasopressin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004305:Dose-Response Relationship, Drug; D005260:Female; D006838:Hydrocarbons; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar; D014667:Vasopressins / Q000138:chemical synthesis* / Q000494:pharmacology*
D006838:Hydrocarbons; C121646:argipressin methylenedithioether; D014667:Vasopressins; D001127:Arginine Vasopressin; C030011:carbene; D008697:Methane