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A highly selective chemical modification method targeting tryptophan and its residues

A high-selectivity, chemical modification technology, applied in chemical instruments and methods, peptide preparation methods, organic chemistry, etc., can solve the problems of poor selectivity, difficult to achieve chemical modification of amino acid residue sites, etc., to achieve small impact , excellent durability

Active Publication Date: 2020-09-11
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, tryptophan, tyrosine, and histidine residues can all react with diazonium salts, indicating that strong electrophilic reagents such as diazonium salts have good reactivity to active amino acids, but the selectivity is not good, making it difficult to achieve Chemical modification of specific amino acid residue positions

Method used

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  • A highly selective chemical modification method targeting tryptophan and its residues
  • A highly selective chemical modification method targeting tryptophan and its residues
  • A highly selective chemical modification method targeting tryptophan and its residues

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Embodiment 1, a highly selective chemical modification method for tryptophan and its residues, select the primary arylamine dye C.I. Acid Brown 4 as the primary arylamine modifier, formaldehyde as the aldehyde component, tryptophan, tyrosine, Ten highly active amino acids including histidine, cysteine, serine, threonine, arginine, aspartic acid, lysine, and phenylalanine were used as modified substances.

[0025]

[0026] The chemical modification method is as follows:

[0027] Select 37% (mass %) formaldehyde solution for use.

[0028] Mix C.I. acid brown 4, amino acid, and formaldehyde (aqueous solution) in a molar ratio of 1:1:100. At this time, the mass ratio of water to primary aramide modifier is about 50:1; the pH value of the reaction solution is adjusted to 4.0 (use 3.6 mL of 1mol / L sodium acetate and 16.4mL of 1mol / L acetic acid are prepared, which is a conventional technique), the reaction temperature is 30°C, and the holding time is 24 hours.

[0029] A...

Embodiment 2

[0034] Embodiment 2, a highly selective chemical modification method for tryptophan and its residues, using p-methylaniline as the primary aromatic amine modifier, acetaldehyde as the aldehyde component, and polypeptide A containing tryptophan residues ( The amino acid sequence is Tyr-Glu-Tyr-Ala-Trp-Ser-Ser, wherein Trp is tryptophan, Tyr is tyrosine, Glu is glutamic acid, Ala is alanine, Ser is serine) as the modified substance .

[0035] The chemical modification method is as follows:

[0036] 0.007mmol of polypeptide A, 0.05mmol (5.35mg) of p-methylaniline and 0.15mmol of acetaldehyde; the water in the reaction system was 35mL; the pH value was 4.5, the reaction temperature was 37°C, and the holding time was 22 hours.

[0037] After the reaction, wash with hot water and cold water (washed with deionized water at 60°C and 15°C for 10 h) to remove impurities adsorbed on the polypeptide, filter, wash (wash with water until the eluent is neutral), to dry. The analysis resul...

Embodiment 3

[0039] Example 3, a highly selective chemical modification method for tryptophan and its residues, using C.I. Acid Green 20 as the primary aryl amine modifier, the aldehyde component is methylglyoxal, and mulberry silk containing tryptophan residues as Modified object.

[0040]

[0041] The chemical modification method is as follows:

[0042] 0.35g mulberry silk fabric (containing about 0.007mmol tryptophan) is mixed with 7.5mg (0.07mmol) of C.I. Acid Green 20 and 7.0mmol of methylglyoxal; the water in the reaction system is 15mL; the pH value is 5.0, and the reaction temperature is 30 ℃, holding time 20 hours.

[0043] After the reaction, wash with deionized water at 60° C. and 15° C. for 10 hours each to remove impurities adsorbed on the silk, and dry in the air.

[0044] After the reaction, the silk is dyed brown, and the fiber strength loss rate is measured to be less than 5%. DMF stripping method (100°C, 20min) proved that the dyes covalently bonded with silk tryptoph...

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Abstract

The invention discloses a highly selective chemical modification method for tryptophan and residues of tryptophan. The method comprises the steps that: tryptophan or a substance containing a tryptophan residue is used as a modified object in water, under the action of an aldehyde component, highly selective three-component electrophilic substitution reaction are conducted on aromatic primary aminemodifiers and tryptophan / tryptophan residues in modified products, so that aromatic primary amine modifier molecules are covalently bonded to the tryptophan / tryptophan residues. In the chemical modification method, the aromatic primary amine modifiers have excellent selectivity for the tryptophan and the residues of tryptophan in proteins, and have no significant reactivity with other active amino acids and residues thereof; the covalent bonding forms among the aromatic primary amine modifier molecules and the tryptophan and the residues of tryptophan, and the durability is excellent.

Description

technical field [0001] The invention relates to a highly selective chemical modification method for tryptophan and its residues. Background technique [0002] Protein chemical modification technology is an important direction in the development of modern biotechnology. Any changes in the covalent structure of proteins through the introduction or removal of chemical groups can be called chemical modifications of proteins. Chemical modification is an important means to study the relationship between protein structure and function, and it is also a powerful tool for directional modification of protein properties. There are two main methods of chemical modification of proteins: (1) changing the side chain groups of protein molecules; (2) changing the main chain structure of protein molecules. Among them, the reaction of modifying the side chain structure of amino acid residues in proteins is a simple and efficient chemical modification method, which can modify the properties o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K1/107
CPCC07K1/1077
Inventor 陈维国崔志华江华高普赵玲
Owner ZHEJIANG SCI-TECH UNIV
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