Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative

A technology for gram-positive bacteria and derivatives, applied in the field of carbohydrate chemistry, can solve the problems of long time, high cost, difficulty in vaccine preparation and the like

Active Publication Date: 2018-07-27
JIANGNAN UNIV
View PDF2 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no study on the chemically synthesized C.bolteae cell wall capsular polysaccharide as a vaccine, and the extraction and purification of the polysaccharide structure by biological methods mainly have the following disadvantages: 1) The extraction and purification process is time-consuming and costly, and each time The amount of extraction is small; 2) It is difficult to obtain a product with high purity and a single structure, and the impurities in the product may bring a series of problems and difficulties to the later vaccine preparation

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative
  • Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative
  • Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] The synthesis of embodiment 1 sugar block 3 is as follows figure 1 :

[0070] Specific test operation and steps:

[0071] Compound 8: Under argon protection, commercial D-mannose (40g, 222mmol) was dissolved in acetic anhydride (228mL), sodium acetate (24g, 288.6mmol) was added, stirred at 80°C for two hours, TLC After monitoring the complete reaction of the raw materials, extract with dichloromethane, wash with saturated sodium bicarbonate solution, collect the organic phase, dry over anhydrous sodium sulfate, filter out sodium sulfate with filter paper, and remove the solvent by rotary evaporation to obtain a brown syrup, which is directly put into the next reaction. Dissolve peracetylated mannose in anhydrous dichloromethane (1000 mL), add Molecular sieves, add ethanethiol (25mL), cool to 0°C, add boron trifluoride ether solution (55mL) dropwise, stir and react in ice bath for 30 minutes, rise to room temperature and stir for 32 hours, then add 0.5 equivalent Tri...

Embodiment 2

[0073] The synthesis of embodiment 2 sugar block 4 is as follows figure 2 :

[0074] Specific test operation and steps:

[0075] Compound 11: Under argon protection, commercial diacetone glucose 10 (50g, 191mmol) was dissolved in dimethylformamide (490mL), cooled to 0°C, and sodium hydride (15.4g, 382mmol ), added benzyl bromide (35mL) dropwise, reacted in an ice bath for 30 minutes, raised to room temperature and reacted for 5 hours, after the TLC monitoring of the raw material reaction was complete, added ice water to terminate the reaction, extracted with dichloromethane (3 × 250mL), collected The organic phase was dried with anhydrous sodium sulfate, and filtered to remove sodium sulfate with filter paper to obtain syrup 11 (66.2 g, 189.1 mmol, 99%). 1 H NMR (400MHz, CDCl 3)δ: 7.61~7.08(m,5H,Ph),5.90(d,J=3.7Hz,1H,1-H),4.68(d,J=11.8Hz,1H,PhCH),4.63(d,J= 11.8Hz, 1H, PhCH), 4.58(d, J=3.7Hz, 1H, 2-H), 4.37(dt, J=7.7, 6.1Hz, 1H, 5-H), 4.15(dd, J=7.8, 3.2Hz, 1H, 6-H), 4.11...

Embodiment 3

[0083] The synthesis of embodiment 3 sugar block 5 is as follows image 3 :

[0084] Compound 20: Under the protection of argon, dissolve compound 8 (11.3g, 28.7mmol) in methanol (250mL), add a catalytic amount of sodium methoxide, and react at room temperature for 12 hours. After TLC monitors that the reaction of the raw materials is complete, add a cation exchange resin Adjust the pH to 5-6, filter the resin with filter paper, and remove the solvent by rotary evaporation to obtain a brown syrup, which is directly used for the next reaction. The obtained syrup was dissolved in dimethylformamide (90mL), stirred at room temperature, p-toluenesulfonic acid (735mg, 3.9mmol) and benzaldehyde dimethyl acetal (5mL, 32.8mmol) were added, and the temperature was raised to 60°C for reaction 7 Hours, TLC monitors that after the reaction of the raw material is complete, triethylamine (5 mL) is added to stop the reaction, extracted with dichloromethane (3 × 150 mL), washed with saturated...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of a clostridium bolteae surface capsular polysaccharide structure derivative and belongs to the field of sugar chemistry. The preparation method comprisesthe following steps: taking glucose as a glycosyl donor to obtain a target beta-glycosidic bond; then successfully synthesizing a disaccharide building block through an oxidization-reduction glucoseC-2 site method; then synthesizing a target oligosaccharide structure which takes the disaccharide building block as a repeating unit, such as the gram-positive bacterium surface capsular polysaccharide structure derivative [arrow3]-alpha-D-Manp-(1arrow4)-beta-D-Rhap-(1arrow]5-Linker. A reducing end of decaose is connected with a connecting arm and is used for connecting protein to form a glycoconjugate for carrying out immunology researches. The method provided by the invention has the advantages of simplicity, time saving, labor saving and low cost; the obtained clostridium bolteae surface capsular polysaccharide structure derivative is possibly used for developing and preparing medicine related to autism.

Description

technical field [0001] The invention relates to a preparation method of a capsular polysaccharide structure derivative on the surface of Gram-positive bacteria, belonging to the field of sugar chemistry. Background technique [0002] Autism, also known as autism, was first discovered in clinical medicine by American psychiatrist Leo Kanner and put forward this concept in the late 1930s. The main manifestations of autism are children's socialization disorder, language communication disorder and behavior habit disorder. According to current international commonly cited standards, 1 in every 160 children suffers from autism. Based on this calculation, the number of children with autism in China was about 1.64 million in 2012, and it is increasing at a rate of 10% to 17% every year, reaching one thousandth of the population. Worldwide, autism has received more and more attention and attention. Since 2008, the United Nations General Assembly has designated April 2 as "World Au...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07H5/10C07H13/04C07H9/04C07H3/04C07H3/06C07H1/00C08B37/00G01N33/48
CPCG01N33/48C07H1/00C07H3/04C07H3/06C07H5/10C07H9/04C07H13/04C08B37/00G01N33/6896G01N2800/28C08B37/006C08L5/00C07H15/26Y02P20/55Y02A50/30
Inventor 尹健胡静彼特·泽贝格蔡军涛
Owner JIANGNAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com