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A calf thymus and new technology technology, applied in the field of thymosin preparation, can solve the problems of too many wastes, difficulty in industrialized implementation, and inability to meet clinical applications.
Active Publication Date: 2007-09-12
SHANGHAI SOHO YIMING PHARMA
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[0011] U.S. Patent (USP508,382) reports a preparation method for the synthesis of thymosin α1 by a solid-phase method: a method for synthesizing thymosin α1 using the Bco strategy. The method disclosed in this document uses highly toxic and corrosive reagents, and there are many wastes and complex processes. , the cost is high, and the industrialized implementation has certain difficulties, which cannot meet the needs of clinical application
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Embodiment 1
[0129] In the embodiment, the decapping reagent is a DMF solution of hexahydropyridine, and the weight concentration of hexahydropyridine is 25%.
[0130] (1) Preparation of Fmoc-Asp-(OtBu)-resin
[0131] Take 50g of Rink Amide MBHA resin (0.8mmol / g resin, 40mmol) into a reaction vessel, soak and wash with 500ml of DMF to fully swell the resin, and blow dry with nitrogen. Washed six times with DMF and blown with nitrogen.
[0132] Take 82g (FW: 411.5, 200mmol) of Fmoc-Asp-OtBu, 64.2g (200mmol) of TBTU, and 27.0g (200mmol) of HOBT, dissolve them in 500ml of DMF, add them to the reaction vessel, and react at 25°C for 2 hours. Blow dry with nitrogen, wash with DMF six times, and blow dry with nitrogen.
[0133] Add 500ml of acetic anhydride:DMF (1:1, volume, the same below), and react at 25°C for 1 hour. Blow dry with nitrogen, wash with DMF six times, and blow dry with nitrogen.
[0134] (2) Preparation of Fmoc-Glu(OtBu)-Asp-(OtBu)-resin
[0135] Add 500ml of decapping reag...
Embodiment 2～3
[0196] Adopt the same method and processing condition as embodiment 1, wherein:
[0197] Use Rink Amide AM resin or Rink Amide PEGA resin as the starting material respectively, connect Fmoc-Asp(R1)-R2 with the same method as before, then add decapping reagent, react at 25°C for 2 hours, add Fmoc dissolved in peptide reagent - The mixture of amino acid, TBTU or HBTU and HOBT was reacted at 25°C for 2 hours, and then reacted by cleavage of peptide to obtain 11.2g and 13.1g of white loose block products, with yields of 11.3% and 13.2% respectively.
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Abstract
The invention discloses a new technology to prepare calf thymus alpha 1 (natural existing in thymus cells of calf and other animals), which uses Fmoc-strategy solid phase method, including the following steps: a. taking any one of Rink Amide PEGA resin, Rink Amide AM resin, Rink Amide MBHA resin or Rink Amide PEGA as the starting material, using the amino acid protected by Fmoc as the monomer to hang resin, connecting amino acids in turn to get a protective 28-peptide resin according to the method of solid-phase synthesis, b. using acetic anhydride to close heads during the process in turn, c. removing Fmoc-protective group in turn, d. synchronizing the removal of side-chain protecting group and the cut of peptide to get a crude, e. purifying the crude with antiphase HPLC to get thymosin alpha 1.
Description
technical field [0001] The invention relates to a method for preparing naturally occurring thymosin, in particular to a new process for preparing calf thymus alpha 1. Background technique [0002] Thymosin, Chinese name: thymosin α1; calf thymus alpha 1; thymosin alpha 1; thymus 28 peptide; [0003] English name: Thymosinα1; Thymosin alpha 1; [0004] Product name: Ridaxian, [0005] Chemical Structure: [0006] Ac-Ser-Asp-Ala-Ala-Val-Asp-Thr-Ser-Ser-Glu-Ile-Thr-Thr-L-Asp Leu-Lys-Glu-Lys-Lys-Glu-Val-Glu-Glu-Ala -Glu-Asn-OH [0007] Molecular formula and molecular weight: C 145 h 240 N 44 o 48 S 2 3431.9 [0008] Thymosin α1 was first isolated from bovine thymus. Because tissue extraction is limited by material sources and the yield is extremely low, it is not suitable for mass production. [0009] In 1979, after Wang and others synthesized this product by liquid-phase chemical synthesis, some people successively reported chemical synthesis by solid-phase total ...
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