Structure of Fmoc-Phe-Gly-OH
CAS No.: 169624-67-3
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CAS No. : | 169624-67-3 |
Formula : | C26H24N2O5 |
M.W : | 444.48 |
SMILES Code : | O=C(NCC(O)=O)[C@H](CC1=CC=CC=C1)NC(OCC2C3=CC=CC=C3C4=CC=CC=C24)=O |
MDL No. : | MFCD01318734 |
InChI Key : | WJQWIPAQNBOEBX-QHCPKHFHSA-N |
Pubchem ID : | 11328236 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With dmap; dicyclohexyl-carbodiimide; In chloroform; at 25℃; for 48h;Sonication; | To a suspension of 1-palmitoyl-2-hydroxy-sn-glycero-3-phos-phocholine 6 (0.5002 g, 1 mmol) in 25 mL of CHCl3 were addedFMOC-phe-gly-OH (0.5393 g, 1.2 mmol), DCC (0.2498 g, 1.2 mmol),DMAP (0.1479 g, 1.2 mmol) and 1 g of glass beads. The reaction wassonicated for 48 h at 25 C, the mixture was thenfiltered to removeDCC-urea and glass beads. The solvent was evaporated to one thirdof the volume and then loaded on a silica gel column forchromatography. A stepwise gradient of CHCl3/MeOH (5:1 and 5:2)was applied to elute DMAP and some impurities, followed byCHCl3/MeOH/H2O (65:25:4). The fractions corresponding to theproduct were combined, evaporated, re-dissolved in benzene andfreeze-dried to give 110 as a white solid (0.5352 g, 0.58 mmol, 58%).IR (Nujol): 3297 br m,1728 vs,1693 s,1654 vs,1536 m,1252 w cm1.1H NMR (CDCl3, 200 MHz) d 0.85 (br t, 3H), 1.25 (br s, 24H),1.50 (m, 2H), 2.20 (t, 2H, J = 6.7 Hz), 2.95 (m, 2H), 3.17 (br s, 9H), 3.67(br s, 2H), 3.95-4.30 (br m, 10H), 4.44 (m, 2H), 5.36 (m, 1H),6.15 (m, 1H), 7.21-7.47 (m, 11H), 7.72 (d, 2H, J = 7.4 Hz), 8.66 (m,1H).13C NMR (CDCl3, 50 MHz) d 14.28, 22.85, 24.92, 29.31, 29.52, 29.71,29.83, 29.87, 32.08, 34.04, 38.94, 41.47, 47.13, 54.34, 55.90, 59.63,62.44, 64.18, 66.28, 67.07, 71.96, 120.08, 125.27, 125.47, 126.94,127.26, 127.86, 128.57, 129.63, 137.05, 141.30, 143.90, 156.17, 169.83,172.39, 173.72. Rf (CHCl3/MeOH/H2O 65:25:4) 0.48. Anal. Cald forC50H72N3O11P2.5H2O C, 62.09; H, 8.02; N, 4.34; found: C, 62.33; H,8.03; N, 4.04. FAB-MS MH+ C50H72N3O11PH Calcd: 922.4977, found:922.4981. [a]D25 C -6.73 (c 0.98, CHCl3/MeOH 4:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.9 g | Synthesis of Fmoc-Phe-Gly-NH-(CH2)6NH-Boc To a solution of <strong>[169624-67-3]Fmoc-Phe-Gly-OH</strong> (0.66 g) in anhydrous THF (20 mL) at 0 C. under N2 was added N,N'-dicyclohexylcarbodiimide (0.307 g) and 1-hydroxybenzotriazole hydrate (0.201 g). After stirring for 15 min, N-Boc-1,6-diaminohexane (0.322 g) was added. The reaction mixture was allowed to warm to RT and stirred overnight. Solids were filtered off and they were washed with EtOAc. The filtrate and washings were then concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (0 to 10% MeOH in CH2Cl2) to afford Fmoc-Phe-Gly-NH-(CH2)6NH-Boc as a white solid (0.9 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.2 mg | General procedure: The Fmoc-amino acid-Wang resin (300 mg) was suspended in a 30% piperidine solution in DMF and stirred 50 min at r.t (room temperature).The resin was washed with CH2Cl2 (3×2 mL), EtOAc(3×2 mL), MeOH (3×2 mL) and CH2Cl2 (2 mL), and finally dried in vacuum. The resin was suspended in 5 mL of a DMF:DCM (2:1) mixture and Fmoc-amino acid (3 equiv.), 1-hydroxybenzotriazole (3 equiv.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (3 equiv.) and diisopropylethylamine(3 equiv.) were successively added. The solution was stirred at r.t. for 16 h. After this, the resin was washed with DMF(3×2 mL), CH2Cl2 (3×2 mL), MeOH (3×2 mL) and CH2Cl2 (2 mL), and finally dried in vacuum. Resin was treated with 5 mL of 10% TFA in CH2Cl2 for 1 h. The mixture was filtered and the filtrate was evaporated under reduced pressure to give the crude product. |