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Preparation method of acetic acid redfish calcitonin

A technology of salmon calcitonin acetate and amino acid, which is applied to the preparation methods of peptides, calcitonin, chemical instruments and methods, etc., can solve the problems of low synthesis yield, difficult coupling of amino acids, etc., and achieves complete removal, Reduce the difficulty of refining and reduce the effect of steric hindrance

Inactive Publication Date: 2013-08-21
QINGDAO GUODA BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is that the existing preparation methods all adopt the symmetrical anhydride method when coupling the 32-position amino acid, which makes the coupling of some amino acids more difficult and the synthesis yield is low

Method used

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  • Preparation method of acetic acid redfish calcitonin
  • Preparation method of acetic acid redfish calcitonin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 prepares deprotection reagent

[0023] The preparation method of the deprotection reagent is: dissolve piperidine in the DCM / DMF / NMP solution, and add Triton-100 to prepare the deprotection reagent, wherein the volume ratio of DCM / DMF / NMP=1:1:1 , piperidine accounts for 20% by volume of the deprotection reagent, and Triton-100 accounts for 1% by volume of the deprotection reagent.

Embodiment 2

[0024] The pretreatment of embodiment 2Rink Amide MBHA resin

[0025] Put the Rink Amide MBHA resin with a substitution degree of ≤0.6mmol / g into the reactor, wash it once with DMF, and drain it. Then use appropriate amount of DMF to swell at room temperature, N 2 Blow and stir for about 30 minutes until the resin is fully swelled, and the liquid is drained. Wash again with DMF and drain. The Rink Amide MBHA resin was deprotected at 15°C for 20 minutes to remove the Fmoc protecting group, drained, the deprotection reagent was 3200ml, and the weight concentration of the Rink Amide MBHA resin was 5-10ml / g. The deprotection temperature can effectively protect the peptide chain from being damaged by the heat released by the deprotection reaction, thereby effectively improving product quality. Finally, it was washed successively with DMF, methanol and DMF, and drained. After deprotection, use a glass rod to pick a little resin, indene inspection, deep purple, indicating that Fm...

Embodiment 3

[0026] Embodiment 3 coupling reaction obtains salmon calcitonin acetate resin

[0027] (1) Coupling of the first amino acid

[0028] The feeding ratio of the coupling reaction of the first amino acid is shown in Table 1, and the first amino acid is Fmoc-Cys(Trt)-OH.

[0029] Table 1 The first amino acid coupling reaction feed ratio

[0030] Raw materials / solvents

Feeding amount

The molar ratio of

Rink Amide MBHA resin after pretreatment

400g (100mmol, 0.4mmol / g)

1

Fmoc-Cys(Trt)-OH

175.7g

3

HOB

40.5g

3

DIC

46.5ml

3

DMF

4000ml

[0031] Weigh 175.7g of Fmoc-Cys(Trt)-OH and 40.5g of HOBt into a beaker, add 2000ml of refined DMF to dissolve the above reagents in the beaker. After complete dissolution, put the beaker in an ice bath to cool for 2 minutes, then add 46.5ml DIC to activate the solution for about 8 minutes. If white flocculent foam appears, it indicates that the activa...

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Abstract

The invention discloses a preparation method of acetic acid redfish calcitonin. The preparation method comprises the following steps of: deprotecting Rink Amide MBHA resin by using a deprotection reagent and removing a Fmoc protecting group; sequentially coupling the deprotected Rink Amide MBHA resin serving as a starting material with Fmoc-protected amino acids serving as monomers to obtain acetic acid redfish calcitonin peptide resin, wherein a condensing agent is N,N-diisopropyl carbodiimide (DIC) / 1-hydroxybenzotriazole (HOBt) or benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP) / HOBt; splitting the acetic acid redfish calcitonin peptide resin, adding diethyl ether and precipitating the acetic acid redfish calcitonin peptide resin to obtain reduction type acetic acid redfish calcitonin crude peptide; cyclizing the reduction type acetic acid redfish calcitonin crude peptide to obtain oxidation type acetic acid redfish calcitonin crude peptide; and performing purification, salt conversion, concentration and freeze drying on the oxidation type acetic acid redfish calcitonin crude peptide to obtain the acetic acid redfish calcitonin. According to the preparation method, the yield of the acetic acid redfish calcitonin reaches over 20 percent.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a preparation method of salmon calcitonin acetate. Background technique [0002] Salmon calcitonin acetate can inhibit the activity of osteoclasts; inhibit the dissolution of bone salts, prevent the release of calcium in the bone; improve bone density, effectively relieve pain symptoms; reduce the risk of fractures and lower blood calcium. Therefore, it is mainly used clinically to treat senile osteoporosis, postmenopausal osteoporosis, and hypercalcemia caused by bone metastases. At present, the preparation method of salmon calcitonin acetate mostly utilizes the Fmoc-strategy solid-phase method to prepare salmon calcitonin, which mainly includes the following steps: Fmoc-Rink Amide MBHA resin or Rink Amide AM resin is de-Fmoc-protected and synthesized according to the solid phase The method is to connect various protected amino acids in sequence to obtain the protected thirty-docosopept...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/585C07K1/16C07K1/06C07K1/04
CPCY02P20/55
Inventor 路兵徐伟张鸿雁
Owner QINGDAO GUODA BIOLOGICAL PHARMA
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