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A kind of preparation method of plicanatide

A prika, crude peptide technology, applied in the preparation method of peptide, chemical instrument and method, peptide and other directions, can solve the problems of complex composition, method to be improved, difficult separation and purification, etc., to achieve high yield, considerable economy Practical value, low cost effect

Active Publication Date: 2018-01-19
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the ring formation of this method is carried out twice in the solution, the components in the solution are complex, and the separation and purification are difficult, so the method needs to be improved.

Method used

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  • A kind of preparation method of plicanatide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Weigh 10 g (5.1 mmol) of Fmoc-Leu-king resin with a degree of substitution of 0.51 mmol / g, add it to the solid-phase reactor, wash with DMF 3 times, and swell for 3 h. The piperidine:DMF solution with a volume ratio of 1:4 was added to the reactor for reaction, and after the reaction was washed 2 times with DCM and 4 times with DMF. Fmoc-Cys(Acm)-OH 6.34g, HOBt 2.07g, DIC 2.37mL were weighed and dissolved in DMF solution, mixed evenly, added to the reactor, and reacted at room temperature for 2h. The ninhydrin color reaction control end point, the resin is transparent and colorless, indicating the end of the reaction, if it is colored, continue to react to colorless. After the reaction was completed, DCM was washed twice, and DMF was washed four times.

[0045] Repeat the above steps, deprotect and couple Fmoc-Gly-OH, Fmoc-Thr(tBu)-OH, Fmoc-Cys-(Mmt)-OH, Fmoc-Ala-OH, Fmoc-Val-OH in sequence in sequence , Fmoc-Asn(Trt)-OH, Fmoc-Val-OH, Fmoc-Cys(Acm)-OH, Fmoc-Leu-OH, Fm...

Embodiment 2

[0051] Weigh 10 g (2 mmol) of Fmoc-Leu-king resin with a degree of substitution of 0.2 mmol / g and add it to the solid phase reactor. After washing with DMF 3 times, it swelled for 3 h. The piperidine:DMF solution with a volume ratio of 1:4 was added to the reactor for reaction, and after the reaction was washed 2 times with DCM and 4 times with DMF. Fmoc-Cys(Acm)-OH 1.24g, HOBt 0.406g, DIC 0.465mL were weighed and dissolved in DMF solution, mixed evenly, added to the reactor, and reacted at room temperature for 2h. The ninhydrin color reaction control end point, the resin is transparent and colorless, indicating the end of the reaction, if it is colored, continue to react to colorless. After the reaction was completed, DCM was washed twice, and DMF was washed four times.

[0052] Repeat the above steps, deprotect and couple Fmoc-Gly-OH, Fmoc-Thr(tBu)-OH, Fmoc-Cys-(Mmt)-OH, Fmoc-Ala-OH, Fmoc-Val-OH in sequence in sequence , Fmoc-Asn(Trt)-OH, Fmoc-Val-OH, Fmoc-Cys(Acm)-OH, Fm...

Embodiment 3

[0058] Weigh 10 g (6 mmol) of Fmoc-Leu-king resin with a degree of substitution of 0.6 mmol / g, add it to the solid-phase reactor, wash with DMF 3 times, and swell for 3 h. The piperidine:DMF solution with a volume ratio of 1:4 was added to the reactor for reaction, and after the reaction was washed 2 times with DCM and 4 times with DMF. Weigh 7.46 g of Fmoc-Cys(Acm)-OH, 2.44 g of HOBt, and 2.79 mL of DIC, and dissolve them in DMF solution, mix them evenly, and add them into the reactor, and react at room temperature for 2 h. The ninhydrin color reaction control end point, the resin is transparent and colorless, indicating the end of the reaction, if it is colored, continue to react to colorless. After the reaction was completed, DCM was washed twice, and DMF was washed four times.

[0059] Repeat the above steps, deprotect and couple Fmoc-Gly-OH, Fmoc-Thr(tBu)-OH, Fmoc-Cys-(Mmt)-OH, Fmoc-Ala-OH, Fmoc-Val-OH in sequence in sequence , Fmoc-Asn(Trt)-OH, Fmoc-Val-OH, Fmoc-Cys(Ac...

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Abstract

The invention discloses a preparation method of pulikanatide, comprising the following steps: 1) Fmoc-Leu-resin carrier adopts Fmoc solid-phase synthesis method according to the polypeptide sequence sequence of pulikanatide from carbon end to nitrogen end Coupling one by one to obtain peptide resins protected by side chain groups; 2) Peptide resins are sequentially deprotected according to Cys4‑Cys12 and Cys7‑Cys15 respectively, and then oriented to form a ring to obtain fully protected pulikanatide peptide resins; 3) Cleavage The reagent cleaves the peptide resin protected by the side chain group, and 4) after desalting, it is purified and freeze-dried to obtain plicanatide. The preparation process of pulikanatide adopted in the present invention has practical industrial application prospects and considerable economic and practical value.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, in particular to a method for preparing pricanatide by directional cyclization reaction on resin. Background technique [0002] The C-type guanylate cyclase (GC-C) receptor is mainly expressed on the luminal side of small intestinal epithelial cells. GC-C is a multicenter enzyme that includes an extracellular ligand-binding domain, a single-channel transmembrane domain, an active center similar to a tyrosine kinase protein, and a C-terminal GC-C catalyzed by ligand-mediated activation to generate cGMP area. Enterotoxin (ST) causes secretory diarrhea in susceptible individuals by overactivating the signaling pathway of the gut receptor GC-C, the only ST target identified in humans. Correspondingly, knockout of the GC-C-encoding gene in mice resulted in the suppression of ST-induced intestinal secretion and diarrhea. Infectious diarrhoea caused by ST-producing bacteria is a major cause of unsan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/08C07K1/06C07K1/04
CPCY02P20/55
Inventor 朱颐申周云隆韦萍欧阳平凯
Owner NANJING TECH UNIV
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