Preparation method of polypeptide synthesis carbetocin

A technology for synthesis of carbetocin and peptides, which is applied to the preparation methods of peptides, chemical instruments and methods, peptides, etc., can solve the problems of difficulty in popularization and application, difficulty in directional condensation reactions, etc., and achieve less pollution of three wastes and large-scale industry Prospects of globalization and the effect of good product quality

Active Publication Date: 2011-08-31
SHANGHAI SOHO YIMING PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Chinese invention patent No. ZL200910106889.0 discloses a solid-phase method for preparing carbetocin. The amino resin is used as the starting material, and amino acids with Fmoc protection groups are connected in sequence, and the last amino acid is connected with Br-(CH 2 )

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  • Preparation method of polypeptide synthesis carbetocin
  • Preparation method of polypeptide synthesis carbetocin
  • Preparation method of polypeptide synthesis carbetocin

Examples

Experimental program
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Embodiment 1

[0050] 1) Preparation of Fmoc-Gly-Resin

[0051]Weigh 500 grams (0.68mmol / g) of Rink Amide MBHA resin, put it into a polypeptide reactor, soak it with 8000ml DMF to fully swell the resin, and drain it. Add 8000 ml of 20% hexahydropyridine in DMF and shake at 25°C for 35 minutes. Drain, wash three times with DMF, ethanol, DMF respectively, and drain. Fmoc-Gly-OH 260g, HBTU 280g, HOBT 120g, NMM 200ml, DMF 4000ml were added, and the mixture was shaken at 25°C for 1 hour. Drain, wash three times with DMF, and drain.

[0052] 2) Preparation of Fmoc-Leu-Gly-Resin

[0053] Add 5000 ml of 20% hexahydropyridine in DMF and shake at 25°C for 30 minutes. Drain, wash six times with DMF, and drain.

[0054] Fmoc-Leu-OH 310g, HBTU 280g, HOBT 120g, NMM 200ml, DMF 4000ml were added, and the mixture was shaken at 25°C for 1 hour. Drain, wash three times with DMF, and drain.

[0055] 3) Preparation of Fmoc-Pro-Leu-Gly-Resin

[0056] Add 5000 ml of 20% hexahydropyridine in DMF and shake a...

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Abstract

The invention discloses a preparation method of polypeptide synthesis carbetocin. The technical scheme of the method comprises the steps of taking Rink Amide MBHA (methylbenzene hydrogen amine) resin as an initial raw material; taking Fmoc-protected amino acid as a monomer; sequentially connecting amino acid, wherein Cys adopts Fmoc-Cys (CH2CH2CH2COOR)-OH, and the last amino acid uses Fmoc-Tyr (Me)-OH, and obtaining protected nonapeptide resin; removing the Fmoc azyl protected group of Tyr; cutting straight chain peptide from the resin by peptide cutting reagents such as FTA (fault tree analysis) and the like; precipitating a straight chain peptide rough product by adding diethyl ether; performing ring formation reaction by adding BOP (butyl octyl phthalate) /HOBt (oxhydryl benzotriazole)/DMF (dimethyl formamide); and purifying the preparation type HPLC (high performance liquid chromatography) in a separating way to obtain a target product. After the method is used, the each-step peptide connecting yield is more than 99%, the peptide cutting yield is 96.2%, and the gross yield is as high as more than 35%. The preparation method is convenient to industrial implementation, and has a higher industrial prospect.

Description

technical field [0001] The invention relates to a method for preparing carbetocin, in particular to a method for preparing carbetocin synthesized from polypeptides. Background technique [0002] Chinese name: carbetocin, carbetocin acetate [0003] English name: Carbetocin [0004] CAS number: 37025-55-1 [0005] Molecular formula: C 45 h 69 N 11 o 12 S [0006] Structural formula: [0007] [0008] Carbetocin, a new gynecological drug developed by Canadian Ferring Pharmaceutical Co., Ltd. to prevent and control post-cesarean hemorrhage in women, has been launched in my country recently, providing a new option for preventing and controlling postpartum hemorrhage in pregnant women. [0009] Carbetocin is a newly synthesized nonapeptide long-acting oxytocin receptor agonist, which can be injected intramuscularly or intravenously. The clinical trial jointly completed by Peking Union Medical College Hospital, Peking University First Affiliated Hospital and Beijing Ob...

Claims

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Application Information

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IPC IPC(8): C07K1/06C07K7/06
Inventor 周逸明崔颀蔡华成
Owner SHANGHAI SOHO YIMING PHARMA
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