[Synthesis of [1,6-bis(L-alpha, beta-diaminopropionic acid) oxytocin].
A novel derivative of oxytocin containing nonprotein amino acid L-alpha, beta-diaminopropionic acid (L-Dap) was synthesized by 7+2 fragment combination in solution. N beta of all the amino acid necessary was protected by carbobenzoxy (Z) and N beta of L-Dap was protected by tert. -butoxycarbonyl (Boc) . The important intermediate, heptapeptide, was synthesized by the stepwise elongation method using carbobenzoxy amino acid p-nitrophenyl esters in solution. Azide synthesis was used to get the nonapeptide. Z group was removed by treatment with 5% Pd/C and Boc with CF3COOH. Eight new compounds incorporating L-Dap were obtained and confirmed by the amino acid analysis and mass spectral detection.
Wu
Kaiqun
K
West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Weng
Lingling
L
Zheng
Hu
H
D002851:Chromatography, High Pressure Liquid; D010121:Oxytocin / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C519893:1,6-bis(L-alpha, beta-diaminopropionic acid) oxytocin; D010121:Oxytocin