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Method for preparing vapreotide
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A vaprotide and vaprotide molar technology, applied in the preparation method of peptide, chemical instrument and method, peptide and other directions, can solve the problems of low application value, unfavorable industrial production, complicated operation, etc., and achieve low cost, The effect of less input of raw materials and simple reaction operation
Inactive Publication Date: 2012-07-04
HYBIO PHARMA
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Problems solved by technology
[0003] At present, there is no report on the synthesis process of vapreotide in China; although there are reports on the synthesis process of vapreotide abroad, most of them are liquid-phase synthesis processes, which are complicated to operate, are not conducive to industrial production, and have low application value.
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Embodiment 1
[0036] Example 1. Preparation of Fmoc-Trp(Boc)-RinkAmide resin
[0037] 1. Put 50g of Rink Amide Resin (Sub=0.8mmol / g) into the reaction flask, add DMF to wash twice, and then swell with DMF for 30 minutes.
[0038] 2. Use 20% DBLK to remove the Fmoc protective group of Rink Amide Resin. After removal, wash 4 times with DMF and 2 times with DCM, and detect with ninhydrin detection method. The resin is reddish brown.
[0039] 3. Weigh 63.2g Fmoc-Trp(Boc)-OH and 19.5g HOBT, add 500ml DMF and 24.4ml DIC, dissolve, add to the reaction flask, start the reaction.
[0040] 4. After reacting for 2h, the reaction is finished, DMF is washed three times, 56.4ml acetic anhydride, 48.4ml pyridine are mixed in 400ml DMF, added to the reaction flask and sealed for two hours, then washed with DMF 3 times, DCM washed 2 times, methanol Wash twice and use it directly in the next step of amino acidcoupling.
Embodiment 2
[0041] Example 2. Preparation of Fmoc-Cys(Trt)-Trp(Boc)-Rink Amide Resin
[0042] 1. After washing Fmoc-Trp(Boc)-Rink Amide Resin with DMF, remove Fmoc with 20% DBLK, then wash 4 times with DMF, wash 2 times with DCM, and detect with ninhydrin detection method. The resin is yellow.
[0043] 2. Weigh 70.2g Fmoc-Cys(Trt)-OH, 19.5g HOBT, add 500ml DMF and 24.4ml DIC, dissolve, add to the reaction flask, start the reaction.
[0044] 3. React for 1.5h, detect by ninhydrin detection method, the resin is transparent, and the reaction is finished.
[0045] 4. At the end of the reaction, DMF was washed 3 times, and amino acids were coupled one by one according to the peptide sequence of vaparotide until the last amino acid.
Embodiment 3
[0046] Example 3. Oxidation of Vaparotide
[0047] 1. Weigh 203.2g of iodine and dissolve it in 500ml of N,N-dimethylformamide. After the dissolution is completed, add it to the reaction flask to start the oxidation reaction. The temperature of the reaction system is 35°C.
[0048] 2. Oxidation is over for 20h.
[0049] 3. DMF was washed 5 times, DCM washed 4 times, and finally methanol was added to wash 3 times, and then drained to obtain 166 g of Vapratide-Rink Amide Resin.
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Abstract
The invention discloses a method for preparing vapreotide, comprising the following steps: 1) starting from Fmoc-Trp(Boc)-OH and Rink Amide resin to obtain Fmoc-Trp(Boc)-Rink Amide resin; 2) coupling the Fmoc-Trp(Boc)-Rink Amide resin by a solidphase synthesis method to obtain linear vapreotide-Rink Amide resin according to the peptide sequence; 3) utilizing a solid phase to oxide the vapreotide-Rink Amide resin; and 4) cracking the vapreotide-Rink Amide resin, purifying and freeze-drying to obtain the vapreotide. The invention utilizes iodine to oxide the linear vapreotide resin in the solid phase, thereby avoiding the trouble brought by traditional liquid phase oxidation and improving oxidation yield by 10%-20%. The process of the invention has the characteristics of simple reaction operation, low raw material investment, low cost, high yield and the like, the total reaction yield can reach 68%, and the purification of crude peptide can reach 85%. Therefore, the method has considerable economic value and practical value.
Description
Technical field [0001] The invention relates to a synthetic process for preparing Vapreotide. Background technique [0002] The product contains Vapratide, its molecular structure is: D-phenylpropionyl-L-cysteyl-L-tyrosyl-D-tryptophan-L-lysyl-L-valyl-L -Cysteinyl-L-tryptophan (2-7 disulfide bond), is a highly effective 8-peptide homolog of growth hormone release inhibitor 14 peptide. In vitro experiments have shown that this product can significantly inhibit the secretion of the pancreas, its strength is stronger than the natural growth hormone release inhibitor, and the duration is longer. Studies conducted with experimental dogs have shown that the effect of this product on the pancreas is similar to artificially prepared growth hormone release inhibitor 14 peptide (SS14) and atropine, but inhibits bicarbonate (HCO 3 -) The secretion effect is 2 to 4 times that of SS14. It can inhibit the secretion of protease at a lower dose, and the effect lasts longer than SS14. Vapratide ...
Claims
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Application Information
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