Peptide synthesis using novel S-sulfocysteine derivatives.
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.
Maugras
I
I
Bachem Feinchemikalien AG, Bubendorf, Switzerland.
Gosteli
J
J
Rapp
E
E
Nyfeler
R
R
D000595:Amino Acid Sequence; D001127:Arginine Vasopressin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D002852:Chromatography, Ion Exchange; D003408:Cresols / Q000737:chemistry; D003545:Cysteine / Q000031:analogs & derivatives* / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013886:Thiosulfonic Acids / Q000737:chemistry
D003408:Cresols; D004220:Disulfides; D010455:Peptides; D013886:Thiosulfonic Acids; D001127:Arginine Vasopressin; C032538:4-cresol; C011119:S-sulphocysteine; D003545:Cysteine