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Synthetic method for somatostatin

A technology of somatostatin and synthesis method, which is applied in the field of liquid phase synthesis of somatostatin, can solve the problems of steric hindrance, reduction of product optical rotation, hindering amino acid synthesis and the like

Active Publication Date: 2009-11-04
LANZHOU UNIVERSITY +1
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  • Abstract
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Problems solved by technology

Although it has the advantages of fast peptide incorporation, high yield, and short cycle, there are still problems: with the growth of the synthesized peptide chain, steric factors such as steric hindrance will appear, hindering the synthesis of amino acids, and the synthesis process is easy to racemize. , so that the optical rotation of the product is reduced
Therefore these technical schemes are all difficult as the method for mass production

Method used

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  • Synthetic method for somatostatin

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Embodiment Construction

[0050] Step 1, Fragment I: Synthesis of TFA Thr(Bzl)-Phe-Thr(Bzl)-Ser(Bzl)-Cys(MeOBzl)-OBzl

[0051] Weigh 4.1g (13.9mmol) of Boc-Ser(Bzl)-OH and dissolve it in 50ml of tetrahydrofuran, add 1.53ml (13.9mmol) of N-methylmorpholine, slowly add 1.8 ml (13.9 mmol) of isobutyl chloroformate, after 2-4 minutes, add 20 ml of a tetrahydrofuran solution of 4.6 g (13.9 mmol) of Cys(MeOBzl)-OBzl pre-cooled to below 0°C in the refrigerator. After the reaction was maintained at the low temperature for 30 minutes, the ice-salt bath was removed, and the reaction was resumed at room temperature for 4-6 hours, and the reaction was detected by TLC. Filter to remove salt, concentrate the filtrate, dissolve the residue in ethyl acetate, wash with 5% NaOH, water, 5% HCl, water, and saturated brine successively, dry with anhydrous NaSO4, concentrate and remove the solvent under reduced pressure to obtain a white solid Boc-Ser(Bzl)-Cys(MeOBzl)-OBzl 8.04g, yield 95%.

[0052] Pour 8.04 g of the obt...

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Abstract

The invention relates to a liquid phase synthetic method for somatostatin, which is as follows: firstly, four segment peptides of Thr(Bzl)-Phe-Thr(Bzl)-Ser(Bzl)-Cys(MeOBzl)-Bzl, Boc- Phe-Trp-Lys(z)-OH, Boc-Asn-Phe-OH and Boc-Ala-Gly-Cys(MeOBzl)-Lys(z)-OH are respectively and total synthesized; and then EDCI / HOBt is used for fragment condensation to synthesize total protective reducibility tetradecapeptide; protecting groups possessed by trifluoromethanesulfonic acid and methyl-phenoxide system de-peptide chain are used for obtaining reducibility somatostatin which is oxidized to obtain somatostatin crude product; the somatostatin crude product is separated and purified by a C18 preparative column, is frozen and dried to obtain the somatostatin.

Description

technical field [0001] The invention relates to a liquid phase synthesis method of somatostatin. Background technique [0002] Chinese name: somatostatin. Other names: growth hormone releasing inhibitory hormone. Trade name: Shitanin. English name: Somatostatin, Stilamin. [0003] The structural formula is: [0004] Molecular formula: C 76 h 104 N 18 o 19 S 2 ;Molecular weight: 1637.8. [0005] Somatostatin is synthesized by the cells of the median eminence of the hypothalamus and the islets of the pancreas. In 1973, it was first isolated from the hypothalamus by Burgus and Brazean et al. and its structure was elucidated. The chemical structure is fourteen peptides with a pair of disulfide bonds in the molecule. Synthetic somatostatin has become a commodity for clinical use, and was included in the European Pharmacopoeia in 1997. [0006] The pharmacological effects of somatostatin are as follows: ① It can inhibit the secretion of growth hormone, thyroid stimu...

Claims

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Application Information

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IPC IPC(8): C07K7/08C07K1/06C07K1/02A61P5/02A61P5/08A61P5/48A61P1/04A61P1/18A61P7/04
CPCY02P20/55
Inventor 达朝山苏亚宁洪满贵保英明曹福军
Owner LANZHOU UNIVERSITY
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