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Method for preparing buserelin by liquid-phase total synthesis

A total synthesis, liquid-phase technology, applied in the preparation methods of peptides, chemical instruments and methods, organic chemistry, etc., can solve problems such as lack of large-scale production of buserelin, shorten the synthesis steps, improve the yield, The effect of mild reaction conditions

Inactive Publication Date: 2018-01-19
HEFEI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, domestic peptide companies do not yet have the conditions for large-scale production of buserelin, and its source mainly relies on imports

Method used

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  • Method for preparing buserelin by liquid-phase total synthesis
  • Method for preparing buserelin by liquid-phase total synthesis
  • Method for preparing buserelin by liquid-phase total synthesis

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Embodiment Construction

[0032] The present invention will be described in detail below in conjunction with the examples, so that those skilled in the art can better understand the present invention, but the present invention is not limited to the following examples.

[0033] In the present invention, "appropriate amount" and "approximately" indicate that the amount of the substance used is not critical to the reaction, there is no need to limit the specific range, and it can be added in multiple times, and those skilled in the art can choose according to experiments.

[0034] In the present invention, "appropriate time" means that the time is not critical to the reaction, and there is no need to limit the specific range, and those skilled in the art can choose according to experiments.

[0035] A liquid-phase total synthesis method for preparing buserelin, using the combined strategy of Boc and Fmoc protection, completes the total synthesis with a 4+5 synthetic route and acyl azide coupling, including...

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Abstract

The invention belongs to the technical field of pharmacy, relates to a polypeptide type medical compound, and in particular relates to a method for preparing buserelin by liquid-phase total synthesis.The buserelin is obtained by totally synthesizing tetrapeptide H-D-Ser(tBu)-Leu-Arg-Pro-NHEt and pentapeptide PGlu-His-Trp-Ser-Tyr-NHNH2 in an acyl azide coupling manner through combined protection by Boc and Fmoc. A C terminal tetrapeptide (H-D-Ser(tBu)-Leu-Arg-Pro-NHEt) of the buserelin is subjected to technical improvement; Boc-D-Ser(tBu)-OH is applied to liquid-phase synthesis of the buserelin for the first time; Boc removal is realized under an acidic condition and tert-butyl is not influenced; finally, Boc-Pro-OH, Boc-Arg(NO2)-OH, Boc-Leu-OH and Boc-D-Ser(tBu)-OH are used as basic reagents, so that the yield of the tetrapeptide is improved, and the cost is remarkably is reduced; reaction conditions and the cost are relatively proper. A result shows that the yield of synthesizing a tetrapeptide segment is easy to improve and the purification is facilitated by a manner of removing nitryl again after tetrapeptide synthesis is finished. The prepared buserelin can be used for clinically treating diseases including breast cancer, prostate cancer, endometriosis, infertility and the like, can be widely applied to the pharmaceuticals industry and has extremely high economic value andsocial value.

Description

technical field [0001] The invention belongs to the technical field of pharmacy and relates to polypeptide pharmaceutical compounds, in particular to a method for preparing buserelin through liquid-phase total synthesis. Background technique [0002] Buserelin (Buserelin) is an analog of gonadolibern (gonadotrpin-releasing hormone, GnRH), because the ability of the substance to stimulate luteinizing hormone (Luteinizing hormone, LH) is stronger than that of follicle-stimulating hormone (Follicle stimu-lating hermone, FSH), it is also called luteinizing hormone-releasing hormone (Luteinizing hormone-releasing hormone, LHRH). Buserelin, as an analogue of GnRH, has attracted people's attention because it is a super agonist, and has been used in the clinical treatment of breast cancer, prostate cancer, endometriosis or infertility and other diseases. At present, domestic peptide companies do not have the conditions for large-scale production of buserelin, and its source mainly ...

Claims

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Application Information

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IPC IPC(8): C07K7/23C07K1/06C07K1/02
CPCY02P20/55
Inventor 董华泽程华毕建洪谢冬凌波
Owner HEFEI NORMAL UNIV
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