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General procedure: Peptides were synthesized by solid-phase peptide synthesis using the Fmoc/iBu-orthogonal strategy on a 2-chlorotritly chloride resin (100-200 mesh, 1% DVB, 1.6 mmol-g 1) or a Fmoc- Rink-Amid-2CT resin (200-400 mesh, 1 % DVB, 0.68 mmol-g 1). A peptide synthesis vessel was charged with 2-chlorotrityl chloride resin and DCM (30 ml. g 1 resin). The suspension was shaken with the aid of a Heidolph Vibramax 100 for 30 min at 23 C. The liquid was removed via vacuum filtration, and a solution of Fmoc-protected amino acid (4.00 equiv) and DIPEA (10.0 equiv) in DCM (30 ml. g 1 resin) was added into the peptide synthesis vessel. The resulting suspension was shaken for 15 hours at 23 C, and then the liquid was removed via vacuum filtration. The resin was washed with DCM (3 * 20 ml. g 1 resin * 2 min), and a solution of DIPEA, MeOH, and DCM (1 :2:17, v:v:v, 30 ml. g 1 resin) was added into the peptide synthesis vessel. The suspension was shaken for 1 hour at 23 C, and then the resin was washed sequentially with DMF (2 * 20 ml. g 1 resin), DCM (2 * 20 ml. g 1 resin), MeOH (2 * 20 ml. g 1 resin), and Et20 (2 * 20 ml. g 1 resin). The resin was dried under vacuum, and the loading efficiency was determined by UV-vis spectroscopy at 289.8 nm.9 General washing procedure: Into the peptide synthesis vessel containing resin was added the stated washing-solvent (20 ml. g 1 resin). The suspension was shaken for 2 minutes at 23 C, and then the liquid was removed via vacuum filtration. Into the peptide synthesis vessel containing resin-bound Fmoc-protected peptide was added 20% piperidine in DMF (v:v, 20 ml. g 1 resin), and the suspension was shaken for 5 minutes at 23 C. Then the liquid was removed via vacuum filtration. This deprotection sequence was repeated once, and then the resin was washed with DMF (3 x 20 ml. g 1 resin* 2 min). A round-bottom flask equipped with a Teflon-coated magnetic stirring bar was charged with Fmoc-protected amino acid (Fmoc-(AA)-OH, 4.00 equiv), HBTU (3.90 equiv), HOBt hydrate (3.90 equiv), DIPEA (8.00 equiv), and DMF (10 mL g 1 resin). The solution was stirred for 15 minutes at 23 C and was then added into the peptide synthesis vessel. The vessel was shaken for 90 minutes at 23 C, and then the liquid was removed via vacuum filtration. The resin was washed with DMF (3 x 10 ml_-g 1 resin x 2 min). A round-bottom flask equipped with a Teflon-coated magnetic stirring bar was charged with [Fmoc-Tyr(RuCp)-OH]-CF3C02 (S3) (2.00 equiv), HBTU (1.90 equiv), HOBt hydrate (1.90 equiv), DIPEA (16.0 equiv), and DMF (10 ml_-g 1 resin). The solution was stirred for 1 minute at 23 C and was then added into the peptide synthesis vessel. The vessel was shaken for 2 h at 23 C, and then the liquid was removed via vacuum filtration. The resin was washed with DMF (3 x 10 ml. g 1 resin x 2 min). The resin was washed with DCM (3 x 20 mL g 1 resin x 2 min). Then a solution of 20% of hexafluoroisopropanol (HFIP) in DCM (v:v) (50 mL g 1 resin) was added to the resin, and the suspension was shaken for 20 minutes at 23 C. The liquid was collected via vacuum filtration, and a solution of 20% of HFIP in DCM (v:v, 50 mL g 1 resin) was added to the resin, and the suspension was shaken for 50 minutes at 23 C. The liquid was collected via vacuum filtration, and the combined organic layers were concentrated in vacuo to dryness and were analyzed via LC-MS. |
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