Sheikhhosseini, E., Balalaie, S., Bigdeli, M. (2016). Synthesis of nocistatin C-terminal and it’s amide derivatives as an opioid peptide. Iranian Journal of Pharmaceutical Research, 15(3), 337-342. doi: 10.22037/ijpr.2016.1874
Enayatollah Sheikhhosseini; Saeed Balalaie; Mohammadali Bigdeli. "Synthesis of nocistatin C-terminal and it’s amide derivatives as an opioid peptide". Iranian Journal of Pharmaceutical Research, 15, 3, 2016, 337-342. doi: 10.22037/ijpr.2016.1874
Sheikhhosseini, E., Balalaie, S., Bigdeli, M. (2016). 'Synthesis of nocistatin C-terminal and it’s amide derivatives as an opioid peptide', Iranian Journal of Pharmaceutical Research, 15(3), pp. 337-342. doi: 10.22037/ijpr.2016.1874
Sheikhhosseini, E., Balalaie, S., Bigdeli, M. Synthesis of nocistatin C-terminal and it’s amide derivatives as an opioid peptide. Iranian Journal of Pharmaceutical Research, 2016; 15(3): 337-342. doi: 10.22037/ijpr.2016.1874
Synthesis of nocistatin C-terminal and it’s amide derivatives as an opioid peptide
2Peptide Chemistry Research Center, K. N. Toosi University of Technology
3Kharazmi (Tarbiat Moallem) Uinversity, 43 Mofateh Ave., Tehran
Abstract
A new biological active hexapeptide of C-terminal of nocistatin, contains Glu-Gln-Lys-Gln-Leu-Gln sequence was synthesized according to solid phase peptide synthesis on the surface of 2-chloro tritylchloride resin and using fmoc-protected amino acids in the presence of TBTU (O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyl uranium tetrafluoroborate) as a coupling reagent. Then, amidation of the C-terminus of peptides was carried out using NH4Cl and alkyl ammonium chloride (RNH3Cl) in the presence of TBTU and a tertiary amine (DIPEA) as the base at room temperature in good to high yields. Cleavage of the desired peptides from the surface of the resin after the addition of TFA (1%) provided the protected peptides. All of the products were purified using preparative HPLC and structures were assigned according to MALDI-mass spectrometry data.
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