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Amino acid connected with polyethylene glycol and preparation method and application for amino acid

A polyethylene glycol and amino acid technology, applied in the direction of medical preparations of non-active ingredients, chemical instruments and methods, carrier binding/immobilizing peptides, etc., can solve the problems of not having side chain groups, etc., and achieve improved pharmacokinetics learning effect

Inactive Publication Date: 2012-12-19
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has many limitations when used for PEGylation of small peptides: one is that the amino acids of small peptides may not have side chain groups that can bind to activated PEG

Method used

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  • Amino acid connected with polyethylene glycol and preparation method and application for amino acid
  • Amino acid connected with polyethylene glycol and preparation method and application for amino acid
  • Amino acid connected with polyethylene glycol and preparation method and application for amino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Preparation of mPEG-CO-ε-NH-Lys

[0045] Reaction formula:

[0046]

[0047] Take 1g monomethoxy polyethylene glycol acid 1000 (0.001mol), 0.74g α-tert-butoxycarbonyl-L-lysine (0.003mol) and 0.62g dicyclohexylcarbodiimide (DCC, 0.003mol ) was dissolved in 100ml of dichloromethane, stirred and refluxed at room temperature for 16 hours. The mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure and dried in vacuo. The obtained solid matter was dissolved in 100ml of dichloromethane, and an appropriate amount of trifluoroacetic acid was added, stirred, then concentrated by rotary evaporation at 55°C and dried in vacuo. 100ml of cooled diethyl ether was added to the filtrate, and the resulting precipitate was filtered and dried in vacuo. The product mPEG-CO-ε-NH-Lys was 1.52g.

Embodiment 2

[0048] Embodiment 2: Preparation of mPEG-CO-His

[0049] Reaction formula:

[0050]

[0051] Dissolve 1 g of monomethoxypolyethylene glycol acid 1000 (0.001 mol) in 50 ml of dichloromethane, add thionyl chloride (2 ml, 0.004 mol) in dichloromethane, and stir overnight at room temperature. The mixture was rotary evaporated, and the resulting solid residue was dried in vacuo. The resulting solid matter was dissolved in 100 ml of dichloromethane, and 0.77 g of α-tert-butoxycarbonyl-L-histidine (0.003 mol) and 0.6 ml of triethylamine were added, and stirred overnight at room temperature. Filtrate, add an appropriate amount of trifluoroacetic acid to the filtrate and stir, then concentrate by rotary evaporation at 55°C and dry in vacuo. The obtained solid matter is dissolved in 50ml of dichloromethane and dried with anhydrous magnesium sulfate. After filtering, add 100ml of cooling diethyl ether to the filtrate. The resulting precipitate was filtered and dried in vacuo. The p...

Embodiment 3

[0052] Embodiment 3: Preparation of mPEG-CO-Trp

[0053] Reaction formula:

[0054]

[0055]Take 4g of monomethoxy polyethylene glycol acid 4000 (0.001mol) and dissolve it in 50ml of dichloromethane, add thionyl chloride (2ml, 0.004mol) in dichloromethane solution, and stir overnight at room temperature. The mixture was rotary evaporated, and the resulting solid residue was dried in vacuo. The obtained solid matter was dissolved in 100 ml of dichloromethane, 0.91 g of α-tert-butoxycarbonyl-L-tryptophan (0.003 mol) and 0.6 ml of triethylamine were added, and stirred overnight at room temperature. Filtrate, add an appropriate amount of trifluoroacetic acid to the filtrate and stir, then concentrate by rotary evaporation at 55°C and dry in vacuo. The obtained solid matter is dissolved in 50ml of dichloromethane and dried with anhydrous magnesium sulfate. After filtering, add 100ml of cooling diethyl ether to the filtrate. The resulting precipitate was filtered and dried in v...

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Abstract

Amino acid connected with polyethylene glycol is provided with the following structural formula of R-PEG-X-amino acid, wherein the PEG is a polyethylene glycol chain, the R is hydroxyl or alkoxy of the PEG, the alkoxy can be selected from C1-C12 alkoxy, cyclo alkoxy or aralkyl alkoxy, and the X is a heteroatom without activated hydrogen except for alpha-carboxyl and alpha-amino in the amino acid. When the amino acid connected with the polyethylene glycol is used for synthesizing polypeptides, the polypeptides of the polyethylene glycol chain in a specific position can be obtained, and the polypeptides improve pharmacokinetics and do not influence original therapeutic effects of the polypeptides. The invention further discloses a preparation method for the amino acid.

Description

technical field [0001] The invention relates to an amino acid linked to a long chain of polyethylene glycol, its preparation method and its use in the synthesis of polypeptides, and is used to prepare polypeptides with long chains of polyethylene glycol. Background technique [0002] With the development of biotechnology, more and more small peptides with biological activity have been found to have therapeutic effects by researchers, such as: thymosin, somatostatin, angiotensin, ajirelin and so on. However, small peptides also have many disadvantages in clinical application, such as prone to immune rejection, poor stability, and faster clearance in the body. Therefore, people have adopted various methods to eliminate the above-mentioned unfavorable factors, one of which is to adopt pegylation technology. [0003] PEGylation technology (PEGylation PEGylation), also known as chemical modification, is one of the most important technologies in molecular altering structure chemi...

Claims

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Application Information

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IPC IPC(8): C08G65/48C07K17/08A61K47/48
Inventor 姚文兵田浤高向东陈阳建宋潇达
Owner CHINA PHARM UNIV
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