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Polypeptide condensing agent for polypeptide drug synthesis and preparation method thereof

A peptide condensing agent and drug synthesis technology, which is applied in the field of amino acid peptides, can solve the problems of long reaction cycle and cumbersome operation procedures, and achieve the effect of simple route, simple synthetic route and less side reactions

Inactive Publication Date: 2019-02-15
重庆奥舍生物化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Currently, no carbocationic peptide condensing agents based on 1-hydroxy-1,2,3-benzotriazin-4(3H)-one have been reported, while condensing agents based on 3-hydroxy-1,2,3-benzotriazine The synthesis process of the oxazine-4(3H)-one carbocation polypeptide condensing agent involves toxic and harmful substances such as methyl anthranilate, sodium nitrite, hydroxylamine and diazotization reactions, and there are long reaction periods and cumbersome operating procedures. shortcoming

Method used

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  • Polypeptide condensing agent for polypeptide drug synthesis and preparation method thereof
  • Polypeptide condensing agent for polypeptide drug synthesis and preparation method thereof
  • Polypeptide condensing agent for polypeptide drug synthesis and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Take 13.2g (100mmol) of tetramethylthiourea, add 100mL of solvent acetonitrile, add 13.5g (100mmol) of sulfuryl chloride, stir and react for 1 hour, add 6.9g (100mmol) of hydrazine hydrochloride and 18.0g of methyl o-nitrobenzoate (100mmol), gradually warming up to reflux reaction for 3 hours, adding sodium tetrafluoroborate 11.0g (100mmol) to the system after the reaction, cooling and separating out a white solid and washing with acetonitrile to obtain the target product polypeptide condensation agent I 33.0g, the yield is 94.2 %, the purity is 99%.

Embodiment 2

[0017] Take 13.2g (100mmol) of tetramethylthiourea, add 100mL of solvent toluene, add 20.3g (150mmol) of sulfuryl chloride, stir and react for 1 hour, add 13.7g (200mmol) of hydrazine hydrochloride and 18.0g of methyl o-nitrobenzoate (100mmol), gradually warming up to reflux reaction for 3 hours, adding sodium tetrafluoroborate 23.0g (200mmol) to the system after the reaction, cooling and separating out a white solid and washing with acetonitrile to obtain the target product polypeptide condensation agent I 33.5g, the yield is 95.7 %, the purity is 98.5%.

Embodiment 3

[0019] Take 13.2g (100mmol) of tetramethylthiourea, add solvent tetrahydrofuran 100mL, add sulfuryl chloride 13.5g (100mmol), stir and react for 1 hour, add hydrazine sulfate 13.0g (100mmol) and methyl o-nitrobenzoate 18.0g (100mmol), gradually warming up to reflux reaction for 3 hours, adding sodium tetrafluoroborate 11.0g (100mmol) to the system after the reaction, cooling and separating out a white solid and washing with acetonitrile to obtain the target product polypeptide condensation agent I 31.5g, the yield is 90.0 %, the purity is 99%.

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Abstract

The invention discloses a polypeptide condensing agent for polypeptide drug synthesis and a preparation method thereof, and belongs to the technical field of amino acid polypeptides. A technical scheme adopted by the invention has key points as follows: the polypeptide condensing agent for the polypeptide drug synthesis is N,N,N',N'-tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-1-yl)urea tetrafluoroborate, and adopts a structural formula as follows: FORMULA. The invention further specifically discloses the preparation method of the polypeptide condensing agent for the polypeptide drug synthesis. By the preparation method, raw materials are common reagents, the synthesis route is simple, a multi-step one-pot reaction condition is mild, the operation is simple, and a diazotization reaction is avoided.

Description

technical field [0001] The invention belongs to the technical field of amino acid polypeptides, and in particular relates to a polypeptide condensing agent used in the synthesis of polypeptide drugs and a preparation method thereof. Background technique [0002] Peptides are an important biologically active substance. Polypeptide synthesis is mainly accomplished by the carboxyl activation method. The earliest method used was to activate amino acids into acid chlorides, azides, symmetrical anhydrides, and mixed anhydrides. These methods have disadvantages such as amino acid racemization, the use of dangerous reagents, and complicated preparation processes. It was superseded by the later peptide condensation reagent method. [0003] The currently used polypeptide condensing agents can be divided into diimine type, phosphorus cation type and urea cation type according to their structure. The first peptide condensing agent was N,N'-dicyclohexylcarbodiimide (DCC), the first car...

Claims

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Application Information

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IPC IPC(8): C07D253/08
CPCC07D253/08
Inventor 崔振伟张玮玮张甫青李玲
Owner 重庆奥舍生物化工有限公司