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Preparation and opioid activities of N-methylated analogs of [D-Ala2, Leu5]enkephalin
Authors:MASAO KAWAI  NORIHITO FUKUTA  NAOKI ITO  TAKATOYO KAGAI  YASUO BUTSUGAN  MUTSUMI MARUYAMA  YOSHIHISA KUDO
Abstract:Analogs of opioid pentapeptide [D-Ala2, Leu5]enkephalin were prepared using two kinds of N-methylation reactions, namely quaternization and amide-methylation. Quaternization reaction with CH3I-KHCO3 in methanol was applied to the deprotected N-terminal group of the pentapeptide derivatives affording trimethylammonium group-containing analogs. [Me3+ Tyr1,D-Ala2, Leu5]enkephalin and its amide were found to show opioid activity on guinea pig ileium assay only slightly lower than the parent unmethylated peptides. Application of amide-methylation reaction using CH3I-Ag2O in DMF to the protected pentapeptide yielded a pentamethyl derivative in which all of the five N atoms were methylated. Deprotection of the derivative gave pentamethyl analogs of [D-Ala2, Leu5]enkephalin, which showed no significant activity on the guinea pig ileum assay and opiate-receptor binding assay.
Keywords:N-methylated [D-AIa2,Leu5]enkephalin  quaternization of primary amino group  N-methylation of peptide linkage  trimethylammonium group-containing analogs of enkephalin
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