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Phloroglucinol glucoside derivatives and preparation method thereof

A technology of phloroglucinol galactose and lactose, which is applied in the field of sugar engineering, can solve the problems of unstable photolysis and poor water solubility, and achieve the effect of increasing water solubility and stability and expanding the scope of application

Active Publication Date: 2013-10-02
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, phloroglucinol also has the disadvantages of phenolic compounds, such as poor water solubility, instability and photolysis properties.
There is no literature report on enzymatic glycosylation modification of phloroglucinol

Method used

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  • Phloroglucinol glucoside derivatives and preparation method thereof
  • Phloroglucinol glucoside derivatives and preparation method thereof
  • Phloroglucinol glucoside derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Phloroglucinol glycoside derivatives, the preparation steps are as follows:

[0028] 1. Preparation of β-galactosidase

[0029] 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);

[0030] The upstream primer is: 5′-CGGGGATGACTCC TTT GGGCAGAAGGTCCA-3'; SEQ ID NO.3

[0031] The downstream primer is: 5′- AAA GGAGTCATCCCCGCCGACCCCCCATCTG-3'; SEQ ID NO.4

[0032] In the primer, TTT encodes phenylalanine, and tryptophan at position 980 is replaced by phenylalanine by PCR;

[0033] PCR amplification conditions were: pre-denaturation at 95°C for 5 minutes; 20 cycles of reaction (denaturation at 9...

Embodiment 2

[0054] The preparation method of phloroglucinol galactoside, following 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 phloroglucinol 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) Purification and detection of phloroglucinol galactoside derivatives are the same as in Example 1.

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

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Abstract

The invention relates to phloroglucinol glucoside derivatives and a preparation method thereof. The preparation method is characterized in that galactosylated modification is carried out on phloroglucinol by using phloroglucinol as a raw material, a low-cost lactose substrate as a galactosyl donor and glycosidase modified by molecules originated from microorganisms as a tool enzyme so as to synthesize multiple phloroglucinol galactoside derivatives. Compared with the raw material phloroglucinol, the synthesized phloroglucinol galactoside derivatives have the advantages that the synthesized phloroglucinol galactoside derivatives contain galactosyl, the water solubility and the stability are improved, the application range is widened, and the synthesized phloroglucinol galactoside derivatives can serve as new chemical synthesis intermediates to be used for deriving and synthesizing new high value-added compounds.

Description

technical field [0001] The invention relates to phloroglucinol glycoside derivatives and a preparation method thereof, in particular to a method for synthesizing phloroglucinol galactoside by using β-galactosidase mutant enzymes, and belongs to the technical field of glycoengineering. technical background [0002] Phloroglucinol (1,3,5-trihydroxybenzene) is an excellent pharmaceutical product, which has been widely used in antibacterial, inhibition of spleen tyrosine activating enzyme, and apple preservation. In recent years, this compound has also become a new type of myotropic non-atropine non-papaverine pure smooth muscle antispasmodic drug, and its injection has been widely used clinically in France and other European countries, and has become the first choice drug for the treatment of spasmodic pain. In addition, phloroglucinol is also an important fine chemical product, which can be used as an intermediate in drug synthesis for the preparation of flavones, isoflavones ...

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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