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Preparation method of 4-methyl umbrella-shaped keto-beta-D-pyran galactoside

A technology of methylumbelliferyl and galactopyranoside, which is applied in the field of galactoside synthesis, can solve the problems of easy decomposition of bromide, unknown yield, and unfriendly waste liquid, and achieve simple post-processing, The effect of reducing production cost and shortening reaction time

Active Publication Date: 2014-07-02
GUANGDONG INST OF MICROORGANISM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

K.F.CHILVERS and J.D.PERRY et al synthesized MU-Gal by the Koenigs-Knorr method. The catalyst is silver salt or mercury salt. During the reaction, bromoglycoside is easy to decompose, and the reaction time is as long as 2-3 days, and the heavy metal accelerator used It will produce a large amount of waste liquid which is not friendly to the environment, and the specific yield is unknown

Method used

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  • Preparation method of 4-methyl umbrella-shaped keto-beta-D-pyran galactoside
  • Preparation method of 4-methyl umbrella-shaped keto-beta-D-pyran galactoside
  • Preparation method of 4-methyl umbrella-shaped keto-beta-D-pyran galactoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Weigh 5.5g of resorcinol and add it to 6.5g of ethyl acetoacetate, heat to dissolve and slowly add it dropwise to 50ml of concentrated sulfuric acid with a volume fraction of 75% (below 4°C). After the dropwise addition was completed and reacted at room temperature for 12 h, the reaction solution was poured into ice water and vigorously stirred, and a solid was precipitated, which was filtered by suction and washed with a large amount of ice water to obtain a pale yellow solid. The white crystalline powder of 4-methylumbelliferone was obtained by recrystallization from absolute ethanol, and the yield was 74.4%. That 1 H NMR spectrum seefigure 1 . 1 H NMR(300MHz,DMSO)δ10.52(s,1H,H-OH),7.59(dd,J=8.7,1.9Hz,1H,H-5),6.80(dd,J=8.7,2.3Hz,1H , H-6), 6.71 (d, J=2.3Hz, 1H, H-8), 6.13 (s, 1H, H-3), 2.36 (s, 3H, CH3).

[0048] Weigh 5g of β-D-galactose pentaacetate, add 33%-35% hydrobromic acid-acetic acid solution 7.5-10ml, react at room temperature for 4h, pour the reaction so...

Embodiment 2

[0052] Example 2: Application of 4-methylumbelliferyl β-D-galactopyranoside in the detection of coliform bacteria

[0053] Experimental materials and sources

[0054] 1. The standard product 4-methylumbelliferone-β-D-galactopyranoside was purchased from APOLLO Technology Co., Ltd.

[0055] 2. Tryptone, Sodium Chloride, Potassium Monobasic Phosphate, Dipotassium Hydrogen Phosphate, and Sodium Lauryl Sulfate

[0056] 3. Escherichia coli ATCC25922, Citrobacter freundii ATCC8090, Enterobacter aerogenes CMCC45103, Klebsiella pheumoniae ATCC10031, Proteus vuigaris CMCC49027, Enterococcus 2 ATCC 2 faecalis Shigella flexneri CMCC51572 and Salmonella trphimurium ATCC14028 were purchased from Guangdong Huankai Microbiology Technology Co., Ltd., and the experimental samples were purchased from supermarkets.

[0057] 1. Pure bacteria detection

[0058] 1) Strains:

[0059] Inoculate the bacteria used in the experiment into the nutrient broth, culture at 37°C for 24 hours, and then it ...

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Abstract

The invention discloses a preparation method of 4-methyl umbrella-shaped keto-beta-D-pyran galactoside. The method comprises the following steps: step 1, preparing 4-methyl umbrella-shaped ketone; step 2, preparing tetra acetyl-Alpha-D-pyran galactoside; step 3, preparing 4-methyl umbrella-shaped keto-2,3,4,6-tetra acetyl-beta-D-pyran galactoside; and step 4, preparing the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside. The method is moderate in reaction condition, namely, the reactions are carried out at a room temperature; heavy metallic salts are not required, so that the environmental friendliness is realized; the yield is high, namely, the one-step yield of glycosylations can reach 73.1% and the total yield of the glycosylations can rach 32.9%. The microbiology experiment proves that the effects of the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside are equal to the effects of an imported substrate, so that the 4-methyl umbrella-shaped keto-beta-D-pyran galactoside can be used for replacing an imported product.

Description

Technical field: [0001] The invention belongs to the field of galactoside synthesis, and in particular relates to a preparation method of 4-methylumbelliferyl-β-D-galactopyranoside. Background technique: [0002] Food safety is related to human life and health, and has attracted great attention all over the world. Food-borne pathogens are an important cause of food-borne diseases and a major hidden danger to food safety. Therefore, timely and effective detection of foodborne pathogenic bacteria contaminated in food is of great significance for the prevention and control of foodborne diseases. [0003] In recent years, chromogenic media technology has been successfully applied to microbial detection. This technology can realize the rapid detection and identification of microorganisms, and has the advantages of accuracy and high sensitivity. 4-Methylumbelliferyl-β-D-galactopyranoside (MU-Gal) is an important fluorescent substrate commonly used to detect coliforms in water a...

Claims

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Application Information

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IPC IPC(8): C07H17/075C07H1/00
Inventor 吴清平马延霞张菊梅郭伟鹏蔡芷荷卢勉飞
Owner GUANGDONG INST OF MICROORGANISM
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