ABSTRACT
New cysteine S-sulfonate derivatives, Boc-Cys(SO3Na)-ONa 2 and Fmoc-Cys(SO3Na)-ONa 3, were prepared and their utility for peptide synthesis examined. The Fmoc derivative 3 was used in the solid-phase peptide synthesis of Arg8-vasopressin 9 via the Bunte salt 7. Satisfactory S-sulfonate stability was observed when p-cresol scavenged the cleavage from the resin. The intermediate 7 was purified by ion-exchange chromatography prior to S-sulfonate cleavage with tributylphosphine.
Subject(s)
Arginine Vasopressin/analogs & derivatives , Cysteine/analogs & derivatives , Peptides/chemical synthesis , Amino Acid Sequence , Arginine Vasopressin/chemical synthesis , Arginine Vasopressin/chemistry , Arginine Vasopressin/isolation & purification , Chromatography, Ion Exchange , Cresols/chemistry , Cysteine/chemistry , Disulfides/chemistry , Molecular Sequence Data , Peptides/chemistry , Peptides/isolation & purification , Thiosulfonic Acids/chemistryABSTRACT
The trityl group was recently introduced for the protection of the side chain carboxamide function of asparagine and glutamine. The 4-methyltrityl (Mtt) group, a structural modification of trityl, is presented here and allows more rapid cleavage from the protected peptides. Procedures for the introduction of the group and comparative cleavage reactions are also presented.
