Abstract:
A METHOD OF PROTECTING THE SULFUR ATOM OF CYSTEINE N PEPTIDE SYNTHESIS BY REACTION WITH B-(N,N-DISUBSTITUTED)AMINOETHYL ISOCYANATE IN WHICH ONE SUBSTITUENT IS METHYL OR EHTYL AND THE OTHER IS BENZYLOXYCARBONYL, T-BUTYLOXYCARBONYL, OR ADAMANTYLOXYCARBONYL. FOR REMOVAL OF THE PROTECTIVE GROUP, THE PEPTIDE IS TREATED WITH A STRONG ACID TO FORM THE ACID SALT OF THE CORRESPONDING MONOSUBSTITUTED N-ETHYL OR N-METHYL AMINO COMPOUND AND THEN MADE ALKALINE TO LIBERATE THE AMINE. THE PROTECTIVE GROUP CLEAVES INTRAMOLECULARLY WITH FORMATION OF A METHYL OR ETHYL-SUBSTITUTED IMIDAZOLONE AND THE PEPTIDE IN WHICH THE CYSTEINE SULFUR ATOM IS PRESENT AS SULFHYDRYL.