[Synthesis of [1,6-bis(L-alpha, beta-diaminopropionic acid) oxytocin]. 2006

Kaiqun Wu, and Lingling Weng, and Hu Zheng
West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

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.

UI MeSH Term Description Entries
D010121 Oxytocin A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION. Ocytocin,Pitocin,Syntocinon
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance

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