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Synthesis method of non-natural sugar amino acid and derivative thereof

A sugar amino acid, non-natural technology, applied in the field of high-efficiency preparation, can solve problems such as synthesis difficulties, limitations, and complex structures

Pending Publication Date: 2022-03-01
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, due to the complex structure and difficulty of synthesis of these compounds, the research on their biological significance is limited.

Method used

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  • Synthesis method of non-natural sugar amino acid and derivative thereof
  • Synthesis method of non-natural sugar amino acid and derivative thereof
  • Synthesis method of non-natural sugar amino acid and derivative thereof

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Embodiment Construction

[0091] In order to better understand the present invention, the general synthesis method of the above contents of the present invention will be further described below through specific embodiments. However, this should not be construed as limiting the invention.

[0092] (Synthesis of 0004-3) Take a tetrafluoroborate (1.5 mg, 0.005 mmol, 0.05 equiv.) and ligand L (2.8 mg, 0.006 mmol, 0.06 equiv.) Quickly seal the reaction tube and replace the argon three times, add 0.5mL of dry and deoxygenated dichloromethane, and react at room temperature for half an hour; take another reaction tube, add tert-butyl carbonate disaccharide 0004-1 (33.0mg , 0.1mmol, 1.0equiv.) and aldimine ester 0004-2 (34.0mg, 0.15mmol, 1.5equiv.), after sealing the argon for three times, inject the solution containing the copper complex into the reaction tube, and add Four triphenylphosphine palladium (5.5 mg, 0.005 mmol, 0.05 equiv.) and triethylamine (15.0 mg, 0.15 mmol, 1.5 equiv.) in dichloromethane were...

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Abstract

The invention provides a novel preparation method of a non-natural sugar amino acid compound. The efficient preparation of a series of non-natural sugar amino acids is realized through the synergistic catalysis of double metals and the control of chiral ligands. The method has the advantages of high reaction overall yield, common and easily available reagents in the process, simple steps and easy operation in the synthesis process, can be widely applied to industry, and lays a material foundation for later biological application of sugar amino acid.

Description

technical field [0001] The invention designs and utilizes the strategy of bimetallic synergistic catalysis, and realizes the efficient preparation of a series of unnatural sugar amino acids and their derivatives through the control of chiral ligands, which belongs to the field of technical inventions. Background technique [0002] Glycoamino acids are hybrid structures of carbohydrates and amino acids that can be used to generate potential glycomimetics and peptide mimetics. Glycoamino acids are aggregated into polypeptides, which can improve the water solubility of polypeptides and protein / protein interactions. Glycoamino acids also exist in nature, and there are many different types, such as the well-known sialic acid and O / N-glycans, which exhibit important biological activities in cell-to-cell and intracellular interactions , including aspects of metastasis, infection, inflammation, and cancer. Due to the instability of natural O / N-glycans in glycosidases and acidic ph...

Claims

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Application Information

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IPC IPC(8): C07D309/30C07D405/04C07F7/18C07D407/04C07D309/10
CPCC07D309/30C07D405/04C07F7/1804C07F7/1892C07D407/04C07D309/10C07B2200/07
Inventor 不公告发明人
Owner LANZHOU UNIVERSITY
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