Method for on-line synthesizing mannose-6-acetate by lipase catalysis

A technology of mannose and lipase, which is applied in the field of online controllable and selective synthesis of mannose-6-acetate catalyzed by lipase, which can solve the problems of long reaction time, low conversion rate and low selectivity, and reduce usage , short reaction time, high conversion and reaction selectivity

Active Publication Date: 2013-07-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present in this patented technology allows for faster and more efficient production of methyl-5-(N)-azolidinone-2-carboxylic acid (MNAc) without requiring long periods or expensive equipment. This results from selecting specific chemicals that can be easily produced by micromachining techniques on silicon chips instead of traditional methods like chemically modifying them afterwards.

Problems solved by technology

This patented describes different ways to make sugurs without generating unwanted impurities or producing colored waste streams when making them through traditional chemical techniques like acid catalysis. However, these current approaches require longer periods of reaction times (>24 hours) and involve complicated steps involving multiple types of molecules involved. These limitations hinder their commercial applications especially because they lack versatility and ease of industrial manufacture.

Method used

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  • Method for on-line synthesizing mannose-6-acetate by lipase catalysis
  • Method for on-line synthesizing mannose-6-acetate by lipase catalysis
  • Method for on-line synthesizing mannose-6-acetate by lipase catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of Mannose-6-Acetate

[0027]

[0028] device reference figure 1 : Mannose (0.4mmol) was dissolved in 10mL tert-amyl alcohol: DMSO=4:1 (v / v) mixed solvent, vinyl acetate (8.4mmol) was dissolved in 10mL tert-amyl alcohol, and then packed in 10mL Ready to use in the syringe. 0.87g of lipase Lipozyme TLIM was evenly filled in the reaction channel of the microfluidic channel reactor, and driven by the PHD2000 syringe pump, the two reaction solutions were separated at 10.4 μL min -1 The flow rate enters the reaction channel through the "Y" joint for reaction, and the temperature of the reactor is controlled at 52°C by a water bath thermostat. The reaction solution flows continuously in the reaction channel for 30 minutes, and the reaction results are tracked and detected by thin-layer chromatography (TLC).

[0029] The reaction solution was collected online by the product collector, the solvent was distilled off under reduced pressure, and the colum...

Embodiment 2-5

[0033] Change the temperature of the microfluidic channel reactor, others are the same as in Example 1, and the reaction results are as shown in Table 1:

[0034] Table 1: Effect of Temperature on Reaction

[0035]

[0036] The results in Table 1 show that when the flow rate is 10.4 μL min -1 , when the reaction time is 30min, the conversion rate increases obviously with the increase of the reaction temperature. When the reaction temperature reaches 52°C, the conversion rate and selectivity of the reaction are the best. The decrease in enzyme activity leads to a decrease in the conversion rate and selectivity of the reaction, so the optimal reaction temperature of mannose acetate in the microfluidic microchannel reactor in the present invention is 52°C.

Embodiment 6-11

[0038] Change the substrate molar ratio of vinyl acetate and mannose in the microfluidic microchannel reactor to be 17: 1 (Example 6), 18: 1 (Example 7), 19: 1 (Example 8), 20: 1 (Example 9), 22:1 (Example 10), 23:1 (Example 11), and others are the same as Example 1. The results are shown in Table 2.

[0039] Table 2: Effect of Mannose to Vinyl Acetate Substrate Ratio on Reaction

[0040] Example Vinyl acetate:mannose Conversion rates[%] selectivity [%] 6 17∶1 55 100 7 18∶1 75 100 8 19∶1 88 100 9 20∶1 95 100 1 21∶1 98 100

[0041] 10 22∶1 97 99 11 23∶1 96 98

[0042] The results in Table 2 show that as the reactant vinyl acetate increases, the conversion rate of the reaction also increases. When the substrate ratio is 21:1, the conversion rate and selectivity of the reaction are optimal, and mannose has basically been quantified Complete conve...

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Abstract

The invention provides a method for on-line synthesizing mannose-6-acetate by lipase catalysis, comprising: using mannose and vinyl acetate, with a mol ratio of 1:17-23, as raw materials, using 0.5-10g of Lipozyme TLIM as a catalyst, and using a mixed solvent of tertiary amyl alcohol and DMSO as a reaction solvent, uniformly filling Lipozyme TLIM in a reaction channel of a microfluidic channel reactor, wherein the internal diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4mm, and the length of the reaction channel is 0.5-1.0m; continuously introducing the raw materials and the reaction solvent into the reaction channel to perform acylation reaction under 40-55 DEG C for 15-35min, on-line collecting the reaction solution, and then obtaining the mannose-6-acetate after conventional post-treatment on the reaction solution. The method of the invention has advantages of short reaction time, high selectivity and high yield.

Description

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Claims

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Application Information

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Owner ZHEJIANG UNIV OF TECH
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