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H<SUB>2</SUB>N-Tyr-Gly-Gly-(2-pyridyl)Ala-Leu-OH[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
10.8%
General procedure: Peptides were synthesized using a solid phase peptide synthesis protocol using an Aapptec FocusXC automated peptide synthesizer coupled with a heating system using the Fmoc chemistry andWang resin as solid support [34]. To prepare the resin for synthesis, a reaction vessel equipped with asintered glass bottom was charged with Fmoc-Leu-Wang resin (0.2 mM), and swelled in a mixture ofdichloromethane and DMF (1:1) for 15 min. The resin was then transferred to a peptide synthesizerreaction vessel. The resin was deprotected twice using 20% piperidine in DMF for 5 min at 70 C.Subsequently, an Fmoc-protected amino acid was double coupled with the Leucine-wang resin bytreating with N,N'-diisopropylcarbodiimide (3.0 equiv., 0.2 M in DMF) and Oxyma (3.0 equiv., 0.2 M inDMF) at 70 C for 8 min. Completion of coupling reactions was monitored by a Kaiser’s test for theinitial peptide [40]. Each coupling was followed by removal of the Fmoc group using 20% piperidinein DMF at 70 C for 5 min and repeated once. The cycle of the Fmoc removal and coupling wasrepeated with subsequent Fmoc-protected amino acids to generate the desired resin-bound peptide.Cleavage of the peptide from resin and concomitant deprotection of the side chain protecting groupswas carried out by shaking in TFA/triisopropylsilane/H20 (95/2.5/2.5; 5 mL), at ambient temperature for3 h. Subsequent filtration aorded the peptide in the filtrate and the volume was reduced to 0.2 mL.Then, the crude peptides were precipitated by adding cold diethyl ether, and the crude peptides werethen purified by RP-HPLC. Synthesized peptides were characterized by NMR, and the high-resolutionmass spectroscopy.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
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