Solid-phase synthesis of oxytocin, desaminooxytocin and 4-Thr-oxytocin using active esters in presence of 1-hydroxybenzotriazole.
Using appropriate amino acid active esters (3 eq.) in presence of HOBt (1 eq.) and employing DPM protection for the thiol function of cysteine, a rapid synthesis of oxytocin in the solid phase has been accomplished. The DPM group has been removed by sodium-liquid ammonia reduction since boiling TFA is ineffective. Desaminooxytocin and 4-Thr-oxytocin have been synthesized using lesser quantities of amino acid active esters (1.5 eq.) in presence of HOBt (1 eq.), but the durations of coupling are longer. The solid-phase synthesis of desamino-oxytocin using appropriate Boc-amino acids in presence of DCCI in toluene medium has been described. Toluene does not exert any significant accelerating influence on the coupling rate as it does when active esters are employed.
D000595:Amino Acid Sequence; D004024:Dicyclohexylcarbodiimide; D004952:Esters; D010121:Oxytocin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D014230:Triazoles
D004952:Esters; D014230:Triazoles; D010121:Oxytocin; D004024:Dicyclohexylcarbodiimide