Solid phase synthesis and biological activities of [Arg(8)]-vasopressin methylenedithioether

Solid phase synthesis of [Arg(8)]-vasopressin methylenedithioether, an anal og of vasopressin which contains an extra methylene group between the two s ulfur atoms of Cys(1) and Cys(6), is described. Methylene insertion occurre d easily when the thiol free peptide on a solid support was treated with te trabutylammonium fluoride in dichloromethane at room temperature for 3 h, T he uterotonic in vitro, presser, and antidiuretic activities of the compoun d were reduced in comparison to [Arg(8)]-vasopressin by one order of magnit ude, (C) 1999 Elsevier Science Ltd. All rights reserved.