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(S)-N-{(S)-1-[(S)-2-(4-Acetoxy-phenyl)-1-carboxy-ethylcarbamoyl]-2-methyl-propyl}-3-[(S)-6-amino-2-((S)-2-amino-5-guanidino-pentanoylamino)-hexanoylamino]-succinamic acid[ No CAS ]
The crude Xmoc-protected peptide was treated with 1.0 g of TBD (97.0 eq.) in a solution of 4 mL of DMF and 4 mL of pyridine. After standing at room temperature for 1 hour the solution was poured into 80 mL of ethyl acetate and stirred from another hour. The white precipitate was filtered and washed with ether (4*10 mL) to give 49 mg (80.33%) of the crude TP5 as an off-white solid which was purified by column chromatography on silica gel (230-400 mesh, 1.5*30-cm packed column) with a eluant consisting of n-BuOH: EtOAc: HOAc: H2 O=1:1:1:1 to give 42 mg (68.85%) of the arginyllysylaspartylvalyltyrosine as a white solid. HPLC analysis was carried out on a Waters Radial Pak 10-mum C18 reverse phase column (0.8*10 cm) under the following conditions:
Example 3 Use of the compound of example 1 in the synthesis of thymopentin Commercial poly(dimethylacrylamide) (1 g) functionalized with a 4-hydroxymethyl-phenoxy-acetyl residue (Pepsyn A 1 meq/g by British C.R.B.) is swollen in dimethylformamide (DMF) and then esterified by treatment with a solution of (Nalpha-Fmoc-(But)Tyr)2O (3.6 mmol) in DMF (16 ml), in the presence of N-methylmorpholine (NMM - 3.6 mmol) and 4-dimethylaminopyridine (DMAP - 0.036 mmol), for 30 minutes.
With palladium on activated charcoal; hydrogen; In methanol; at 20℃; under 3620.13 Torr; for 24h;
To 100 mg dry Pd/C in a hydrogenation bottle wasadded H-RKDVY-OBnDpp 10k in 150 mL methanol. The bottle was placed under 70 PSIH2 atmosphere and shaken at room temperature for 24 hours. The reaction mixture wasfiltered through celite, and evacuated to dryness. The crude was dissolved in a mixture of10% acetic acid (aq) and chloroform, after which the aqueous layer was washed X2 withchloroform. Evacuation of the aqueous layer afforded thymopentin as a white solid; yield,1.09 g, 87%; Retention time on analytical RP-HPLC with 50% MeCN in 0.06% TFAH20 asthe eluent: 1.24 mm, 98.9% purity; HRMS (ESI): m/z calcd for [C30H49N909 + H]:680.3731, found: 680.3730.o our delight, HPLC analysis of the product peptide reveals that the compound is nearly 99% pure without any column chromatography, recrystallization, or polymer supports. The GAP group can be recovered simply by evacuating the chloroformlayer after extraction. Subjecting this raw material to the synthesis methods in FIG. 2 can regenerate BndppOH.
With dipotassium peroxodisulfate; bis(acetylacetonato)palladium(II); silver(I) acetate; acetic acid; at 60℃; for 12h;
Will 1mmol The <strong>[69558-55-0]thymopentin</strong> (7) is added to 4 ml of acetic acid solvent.0.1 mmol of palladium diacetylacetonate was added thereto.1.2mmol ethyl acrylate,2.0mmol silver acetate, 2.0mmol potassium persulfate, reacted at 60 C for 12 hours, after the reaction is over,A saturated aqueous solution of NaCl was added to the reaction mixture, and the mixture was extracted with dichloromethane.After evaporation to dryness, a crude olefinated methoxymethoxycarbonyl-tyrosine-alanine-valine compound was obtained. Olefinated <strong>[69558-55-0]thymopentin</strong>The crude compound was subjected to silica gel column chromatography, and the solution of ethyl acetate and petroleum ether in a volume ratio of 1:5 was used as the mobile phase, and TLC was followed.The eluate having an Rf value of 0.3-0.5 is collected, and the obtained eluate is collected by removing the solvent under reduced pressure and dried to obtain the formula (g).Pure product 29mg (see Figure 6 for mass spectrum).
With chlorotriisopropylsilane; ethane-1,2-dithiol; trifluoroacetic acid In water at -5 - 35℃;
8 Example 8: Application of new non-classical solid-phase synthesis carrier, cleavage reaction.
Prepare a lysate of TFA:TIS:EDT:H2O=85:5:5:5, and pre-cool to -5-5°C. Into a 500mL lysis bottle,Add 17.7g of H-Arg(Pbf)-Lys(Boc)-Asp(OtBu)-Val-Tyr(tBu)-O-(HZ-WSP-E) and 180mL of cold lysate, and heat the oil bath to T = Crack at 30-35°C for 2-3h.After the lysis, the lysate was added to 1800mL of cold methyl tert-butyl ether, centrifuged, washed, dried,Thymopentin (H-Arg-Lys-Asp-Val-Tyr-OH) crude product 6.81g was obtained, the overall yield was 102%, and the crude product HPLC purity was 95%-98%.
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