Method for preparing cordycepin esterified derivative by biocatalysis

A technology for biocatalysis and cordycepin, which is applied in the field of biocatalysis to prepare esterified derivatives of cordycepin, can solve the problems of by-products and products are difficult to separate, poor in selectivity, environmental pollution, etc., and achieves simple and easy-to-control reaction process, easy-to-use products, Environmentally friendly effect

Inactive Publication Date: 2013-05-08
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthesis of cordycepin esterified derivatives by chemical methods requires high energy consumption, poor selectivity, easy to produce by-products and difficult separation of products; and because a large amount of organic solvents and catalysts are used in the reaction process, on the one hand, it will bring serious environmental pollution problems, On the other hand, some toxic chemical substances often remain in the product and there are potential safety hazards

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Put 0.5g cordycepin, 22.5ml acetone, 20mg lipase from Candida antarctica (10,000U / g, Novozymes China Biotechnology Co., Ltd.) and 1.5ml vinyl acetate into the stoppered triangle Place in the bottle, shake in a water bath constant temperature oscillator at 30°C and 150rpm, react for 6 hours, filter to remove lipase, evaporate under reduced pressure (0.02MPa) to remove the organic medium; dissolve the residue with ethanol, and then reduce pressure (0.02MPa) Ethanol was removed by evaporation, and vacuum-dried (35°C, 0.06MPa) to obtain 5′-O-acetyl cordycepin ester derivative C 12 h 15 N 5 o 4 [ 13 C NMR: C6156.2; C2152.4; C4148.9; C8139.7; C5119.1; C1'90.8; C4'77.6; C2'74.6; ); 20.7 (-CH3)], yield 66%.

Embodiment 2

[0021] Put 0.5g cordycepin, 30ml acetone, 20mg lipase from Candida antarctica (10,000U / g, Novozymes China Biotechnology Co., Ltd.) and 3ml vinyl acetate into a stoppered Erlenmeyer flask , placed in a water bath constant temperature oscillator at 30°C and 150rpm, and reacted for 12 hours, filtered to remove lipase, and evaporated to remove the organic medium under reduced pressure (0.02MPa); the residue was dissolved in ethanol, and evaporated to remove under reduced pressure (0.02MPa) Ethanol, vacuum drying (35°C, 0.06MPa) to obtain 5'-O-acetyl cordycepin ester derivative C 12 h 15 N 5 o 4 [ 13 C NMR: C6156.2; C2152.4; C4148.9; C8139.7; C5119.1; C1'90.8; C4'77.6; C2'74.6; ); 20.7 (-CH3)], yield 70%.

Embodiment 3

[0023] Put 0.5g cordycepin, 42.5ml acetone, 100mg lipase from Candida antarctica (10,000U / g, Novozymes China Biotechnology Co., Ltd.) and 5ml vinyl acetate into a stoppered Erlenmeyer flask placed in a water bath constant temperature oscillator at 30°C and 150rpm, and reacted for 24 hours, filtered to remove lipase, and evaporated under reduced pressure (0.02MPa) to remove the organic medium; the residue was dissolved in ethanol, and then evaporated under reduced pressure (0.02MPa) Remove ethanol and dry in vacuum (35°C, 0.06MPa) to obtain 5′-O-acetyl cordycepin ester derivative C 12 h 15 N 5 o 4 [ 13 C NMR: C6156.2; C2152.4; C4148.9; C8139.7; C5119.1; C1'90.8; C4'77.6; C2'74.6; ); 20.7 (-CH3)], yield 92%.

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Abstract

The invention belongs to the fields of biocatalysis and biosynthesis, and relates to a method for preparing a cordycepin esterified derivative by biocatalysis. The method takes acetone, tetrahydrofuran or pyridine as a solvent, takes fatty acid ester with the carbon chain length of C2-C18 as an acyl donor, and uses lipase to catalyze the cordycepin to perform acylation at the reaction temperatureof 30-50 DEG C, thereby synthesizing the cordycepin esterified derivative. The invention has the advantages of mild reaction conditions, environmental friendliness, high selectivity and controllability of the reaction, simple reaction process and the like, and the product is easy to separate from the reaction mixed system.

Description

technical field [0001] The invention belongs to the field of biocatalysis and biosynthesis, and relates to a method for preparing cordycepin esterified derivatives by biocatalysis. Background technique [0002] Cordycepin is a nucleoside compound extracted from Cordyceps sinensis or Cordyceps militaris, and is one of the main active ingredients of the traditional Chinese medicine Cordyceps. Modern pharmacological studies have shown that cordycepin and its derivatives have the functions of improving immunity, anti-fatigue, anti-tumor, anti-inflammatory, anti-bacterial and anti-viral. Therefore, research work on finding more active cordycepin derivatives by modifying the structure of cordycepin compounds has attracted much attention. [0003] At present, the synthesis of esterified derivatives of cordycepin adopts chemical methods at home and abroad. Synthesis of cordycepin esterified derivatives by chemical methods requires high energy consumption, poor selectivity, easy to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P19/40
Inventor 陈志刚顾振新韩永斌
Owner NANJING AGRICULTURAL UNIVERSITY
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