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Preparation method of pyrocatechol galactoside

A technology of catechol and galactoside, which is applied in the field of glycoengineering to achieve the effects of increasing water solubility and stability

Active Publication Date: 2013-09-04
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the development of catechol derivatives mostly adopts chemical methods, and there is only one case report about enzymatic derivatization. Enzymatic Galactosyl Modification of Catechol

Method used

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  • Preparation method of pyrocatechol galactoside
  • Preparation method of pyrocatechol galactoside
  • Preparation method of pyrocatechol galactoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A preparation method of catechol galactoside, the steps are as follows:

[0032] 1. Preparation of β-galactosidase

[0033] Artificially synthesized β-galactosidase gene sequence with GenBank accession number EU734748.1 (encoded protein GenBank accession number is ACE06986.1), ligated it to pET-21b(+) plasmid, and transformed Escherichia coli BL21(DE3) , and then extract the recombinant plasmid, use the plasmid as a template, and introduce a mutation into the enzyme gene sequence by PCR using a mutation kit (Quanjin Easy Mutagenesis System, Beijing);

[0034] The upstream primer is: 5′-CGGGGATGACTCC TTT GGGCAGAAGGTCCA-3'; SEQ ID NO.3

[0035] The downstream primer is: 5′- AAA GGAGTCATCCCCGCCGACCCCCCATCTG-3'; SEQ ID NO.4

[0036] In the primer, TTT encodes phenylalanine, and tryptophan at position 980 is replaced by phenylalanine by PCR;

[0037] PCR amplification conditions were: pre-denaturation at 95°C for 5 minutes; 20 cycles of reaction (denaturation at 95°C ...

Embodiment 2

[0054] A preparation method of catechol-β-D-galactopyranoside, the steps are as follows:

[0055] (1) Use phosphate buffer to prepare a reaction system in which the concentration of lactose is 0.2M, the concentration of catechol is 0.05M, and the amino acid sequence is as shown in SEQID NO.1, and the amount of β-galactosidase added is 10 μg / mL;

[0056] (2) React the reaction system prepared in step (1) in a water bath at 37°C for 20 minutes, boil to terminate the reaction, centrifuge at 12,000 rpm for 20 minutes, and take the supernatant;

[0057] (3) The purification and detection of catechol galactoside are the same as in Example 1.

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

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Abstract

The invention relates to a preparation method of pyrocatechol galactoside, which comprises the following steps of: (1) preparing a reaction system with a phosphate buffer, (2) boiling to terminate reaction after the reaction of the reaction system, centrifuging, and taking a supernate, and (3) separating and drying the supernate, and obtaining pyrocatechol galactoside, wherein for the reaction system, the lactose concentration is 0.1-0.3M; the pyrocatechol concentration is 0.05-0.2M; the addition level of beta-galactosidase with an amino acid sequence shown as SEQ ID NO. 1 (sequence identifier number 1) is 2-10 micrograms / mL. Since mutational beta-galactosidase is used for synthesizing pyrocatechol galactoside, a product contains galactosyl compared with the raw material, pyrocatechol; the water solubility and stability are improved; and the compound can serve as a chemical synthesis intermediate for deriving and synthesizing a new compound with a high added value.

Description

technical field [0001] The invention relates to a preparation method of catechol glycoside derivatives, in particular to a method for synthesizing catechol galactoside by using β-galactosidase mutant enzyme, which belongs to the technical field of glycoengineering. technical background [0002] Phenolic compounds are a class of compounds with an aromatic ring structure, which have a variety of physiological and pharmacological functions, such as catechol has an antioxidant effect, and Avarol can inhibit the replication of HIV. Glycosylation of phenolic compounds can not only increase water solubility, but also improve pharmacological properties and efficacy. For example: hydroquinone is toxic, while hydroquinone-α-glucoside (arbutin) has antibacterial and skin whitening effects; eugenol has the function of repairing hair due to inhibition of 5α-reductase, However, it is easy to sublimate and has a special smell. The eugenol-β-glucoside formed by chemical glycosylation can b...

Claims

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Application Information

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IPC IPC(8): C12P19/44
Inventor 卢丽丽肖敏郭玉川
Owner SHANDONG UNIV
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