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Solid-phase synthetic method of oxytocin

A solid-phase synthesis method and solid-phase synthesis technology, which are applied in the preparation methods of peptides, chemical instruments and methods, oxytocin/vasopressin, etc., can solve the problem of reduced yield and purity of cyclic peptides, long reaction time, The post-processing is cumbersome and other problems, to achieve the effect of low cost, little environmental pollution and easy purification

Active Publication Date: 2013-01-02
YANCHENG KAILI PHARMA
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Problems solved by technology

This process produces a lot of waste liquid, the reaction time is long, and the post-treatment is cumbersome.
Patent CN200510112356.5 discloses a method for solid-phase synthesis of oxytocin. The method uses Rink Amide or Rink MBHA resin as the starting material, and uses TBTU / HOBt or HABU / HOBt as the condensation agent to synthesize step by step; then cut, use air Or use hydrogen peroxide in (10 -3 ~10 -4 mol / L) solution, this method produces more waste liquid, and is prone to intermolecular reactions to form linear or cyclic dimers and polymers. The disadvantage of this method is that the oligomerization reaction between peptide molecules is easy to cause rings Severe reduction in peptide yield and purity

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  • Solid-phase synthetic method of oxytocin

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Embodiment 1

[0025] A solid-phase synthesis method of oxytocin, comprising the following steps:

[0026] Step (1) Preparation of Rink Amide AM Resin

[0027] Weigh 10g of AM Resin (100 mesh, 0.49mmol / g), soak in 50mL DCM for 30min to fully swell the resin, and then wash twice with 50mL DMF (not less than 1min each time). Weigh Rink Amide Linker: 7.93g, HOBt: 1.98g, DIC: 2.24mL, add to 10mL of anhydrous DMF, activate at 0~5℃ for 15min. Add solid-phase synthesis tubes and react at 30°C for 2.0~4.0h. The end point of the reaction is determined by the ninhydrin method. After the reaction is complete, wash with 50mL of anhydrous DMF twice, each time not less than 1.0min. After testing the degree of substitution, The degree of substitution was 0.48mmol / g Rink Amide AM Resin.

[0028] Step (2) Preparation of Boc-Cys(Trt)-Tyr(tBu)-Ile-Gln(Trt)-Asn(Trt)-Cys(Trt)-Por-Leu-Gly-Rink Amide AM Resin

[0029] De-Fmoc protecting group

[0030] Use 70 mL of 25% piperidine / DMF to remove the Fmoc protecti...

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Abstract

The invention provides a solid-phase synthetic method of oxytocin, which comprises the following steps: (I) preparing Rink Amide AM Resin by using AM Resin and Rink Amide Linker as raw materials; (II) orderly coupling Fmoc protecting group-containing amino acids to the Rink Amide AM Resin prepared in the step (I) through a solid-phase synthetic method, removing the protecting group, cracking to obtain linear oxytocin; (III) oxidizing the linear oxytocin, performing purification and freeze drying to obtain the oxytocin. The synthetic process of the invention is simple, low in cost, high in yield, easy for purification, less in environmental pollution, and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of oxytocin synthesis, in particular to a solid phase synthesis method of oxytocin. Background technique [0002] Oxytocin, also known as oxytocin, the English name is Oxytocin, and its molecular formula is: C 43 h 66 N 12 o 12 S 2 , molecular weight is 1007.2, structural formula: [0003] [0004] Oxytocin is a polypeptide hormone uterine contraction drug. It has the following functions: stimulate uterine smooth muscle, lead to its rhythmic contraction, increase frequency and increase muscle tension, and also promote milk secretion by acting on the myoepithelial cells around the mammary acinus. This product is metabolized by liver and kidney, and excreted by kidney , a very small amount is the prototype. It is clinically used in humans and animals to induce labor, oxytocin, postpartum and post-abortion uterine bleeding caused by uterine weakness or poor contraction recovery, placental retention an...

Claims

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Application Information

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IPC IPC(8): C07K7/16C07K1/06C07K1/04
CPCY02P20/55
Inventor 杨毅跃姚程成康国伟蒙相峰鲁尧
Owner YANCHENG KAILI PHARMA
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