A kind of synthetic method of i-type n-glycan antenna

A synthesis method and glycan technology, applied in the field of medicine, can solve the problems of difficult derivatization, low yield, high efficiency and flexibility of I-type N-glycan antenna, etc., and achieve the effect of shortening the synthesis route.

Inactive Publication Date: 2021-11-02
JIANGXI NORMAL UNIV
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the construction of the 2-sugar module containing sialic acid, the α selectivity is only 16:1, and the yield is only 85%. When the 2-sugar module is converted into a donor, the yield operation is cumbersome and the yield is low and expensive Ir (cod) (PPh2Me) 2] PF6 catalysis, its derivatization after synthesis is also very difficult
[0009] Therefore, there are still great difficulties for the high efficiency and flexibility of type I N-glycan antennas

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
  • A kind of synthetic method of i-type n-glycan antenna
  • A kind of synthetic method of i-type n-glycan antenna
  • A kind of synthetic method of i-type n-glycan antenna

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] (1) Synthesis of compound 3

[0080]

[0081] Compounds 1 (60 mg, 0.092 mmol) and 2 (30.6 mg, 0.046 mmol) were dissolved in dry CH 2 Cl 2 (1 mL), add activated 4A MS in N 2 under the protection of After the reaction system was stirred at room temperature for 15 minutes, it was placed at -40°C and continued to stir for 5 minutes. NIS (49.4mg, 0.221mmol) and TfOH (8.0μL, 0.092mmol) were added, and the reaction was continued at low temperature for 2 hours. TLC Point the plate to monitor the reaction is complete, add Et 3 Quench the reaction with N. Filter, wash with saturated sodium bicarbonate and saturated NaCl, and dry over anhydrous sodium sulfate. Filtration and concentration under reduced pressure gave the crude product, and finally column chromatography (PE:EA:DCM=3:1:1) gave white solid compound 3 (49.7mg, 90%).[α] D 25 =-3.0 (c 0.9, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ8.58(d, J=4.8Hz, 1H), 8.05(dd, J=1.2, 8.4Hz, 2H), 7.74(td, J=1.2, 7.6Hz, 1H), 7.64(dd...

Embodiment 2

[0101] (1) The steps and parameters of step (1) in the reaction reference example 1, the difference is that the molar ratio of glycosyl donor compound 1, glycosyl acceptor compound 2, NIS and TfOH is 2:1:5:5 , the concentration of the compound 1 in the first solvent is 0.003mol / L; the glycosylation reaction temperature is -20°C; the yield of the full α configuration is 87%

[0102] (2) Steps and parameters of step (2) in the reaction reference example 1, the difference is that the molar ratio of compound 3 and copper acetate is 1:4, and the concentration of said compound 3 in the second solvent is preferably 0.004mol / L , the solvent is methanol and dichloromethane, the temperature is 50°C, and the yield is 60%

[0103] (3) Steps and parameters of step (3) in the reaction reference example 1, the difference is that the mol ratio of the compound 4 and thioacetic acid is preferably 1:10, and the dichloromethane with a volume ratio of 1:1 and pyridine as solvent. The concentrati...

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 method for synthesizing type I N-glycan antennae. By combining the 2-glycosidation method and MPEP glycosylation scheme, type I antennae can be linearly synthesized from easily obtained monosaccharide cleavage through the longest 7-step line. blocks were obtained with an overall yield of 29%. The present invention solves the problem of poor stereoselectivity and low yield of sialoglycosidation, prepares I-type N-glycan antennae with high stereoselectivity, greatly shortens the synthesis route, provides the possibility for a large number of synthesis, and will greatly promote Research on the mechanism of activity of N-glycans and their structure-activity relationship.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a method for synthesizing type I N-glycan antennae. Background technique [0002] N-glycan (asparagine-linked glycan) antennae are ubiquitous in glycolipids and glycoproteins. Structurally, antennae can be divided into type I and type II. Type I antenna contains α-2,6-linked salivary residues, and type II antenna contains α-2,3-linked salivary residues. Given the critical role of N-glycans in maintaining the normal function of glycoproteins and viral host recognition, the chemical synthesis of N-glycans with well-defined chemical structures has become a widely studied field in glycochemistry. [0003] [0004] 5-position Ac-protected sialic acid [0005] Although N-glycans have a wide range of application prospects, people continue to study them, and N-glycan antennas are the core of the synthesis of N-glycans and are also difficult to synthesize. First of all,...

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 Patents(China)
IPC IPC(8): C07H15/203C07H23/00C07H1/00
CPCC07H1/00C07H15/203C07H23/00
Inventor 孙建松陈健
Owner JIANGXI NORMAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap