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Preparation method of deoxy analog of Echinocandin B

A technology of echinocandins and analogs, applied in the field of antibiotic production, can solve the problems of large pollution, difficult transformation, high transformation, low transformation efficiency, etc.

Inactive Publication Date: 2011-03-30
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of the above method are converted using pure products, the conversion efficiency is low and the cost is high
Trifluoroacetic acid has certain toxicity and is harmful to human body
[0005] The ECBs mixture obtained by fermentation contains a certain amount of related by-products, the components are complex, and there is mutual interference between substances, so the conversion difficulty is higher than that of pure products
In the purification process of ECBs, a large amount of highly toxic organic reagents need to be used, resulting in high pollution and high cost

Method used

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  • Preparation method of deoxy analog of Echinocandin B
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Examples

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Effect test

Embodiment 1

[0059] Dissolve the ECBs mixture (1 g, echinocandin B content at 5%) in ethanol (10 ml) at room temperature, adjust the pH to 3-4 with hydrochloric acid (3 mol / L), and place it in an environment with a temperature of 40 degrees for 48 hours. HPLC detection obtained echocandin B (0.15%), component X (1.7%), component Y (3%), and component D (1.2%). The conversion rate of component echocandin B is 97%, and it is mainly converted into components Y, X, and D.

Embodiment 2

[0061] Dissolve the ECBs mixture (1 g, echinocandin B content 5%) in ethanol (10 ml) at room temperature, adjust the pH to 3-4 with hydrochloric acid (3 mol / L), and place it in an environment with a temperature of 40 degrees for 12 hours. HPLC detection obtained echocandin B (1.5%) and component X (3.7%). The conversion rate of component echocandin B was 70%, mainly converted to component X.

Embodiment 3

[0063] Dissolve the ECBs mixture (1 g, echinocandin B content at 5%) in ethanol (10 ml) at room temperature, adjust the pH to 3-4 with hydrochloric acid (3 mol / L), and place it in an environment with a temperature of 40 degrees for 36 hours. HPLC detection obtained echocandin B (0.5%), component X (4%), and component Y (1.5%). The conversion rate of component echocandinB was 90%, mainly converted into components X and Y.

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Abstract

The invention discloses a preparation method of a deoxy analog of Echinocandin B. The method comprises the following steps of: (1) mixing a fermenting mixture of Echinocandin B with an organic solvent to obtain a solution 1; (2) mixing the solution 1 with an acid water solution to obtain a solution 2; and (3) standing the solution 2 at the temperature of 30-50 DEG C for 12-60h to obtain the deoxy analog of a compound shown as formula I, in the formula, R is linolenic acyl, R1=OH, R2=OH, and R3=OH; the organic solvent is selected from methanol, ethanol, ethyl acetate, acetone or chloroform; acid in the acid water solution is selected from hydrochloric acid, acetic acid or citric acid, wherein the concentration of the acid is 1-3mol / L; and pH of the solution 2 is 1-6.

Description

technical field [0001] The invention relates to the field of antibiotic production, in particular to a method for preparing a deoxygenated echinocandin B analog. Background technique [0002] Echinocandins (hereinafter referred to as ECBs) are a class of natural cyclic lipopeptide compounds discovered in the 1970s with a cyclic hexapeptide core and fatty acid side chain structure. According to different substituents and fatty acid side chains on the cyclic hexapeptide, it can be divided into different compounds. ECBs belong to a new class of antifungal compounds. As glucan synthase inhibitors, they non-competitively inhibit the synthesis of β-(1,3)-D-glucan in the fungal cell wall to play a bactericidal effect. Many similar components can be produced during fermentation (US Pat. No. 4,024,245). Wherein the deoxy analogue of echinocandin B has similar or higher bacteriostatic activity with echocandin B, therefore has development value (U.S. Patent US4024245, US5386010), but...

Claims

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Application Information

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IPC IPC(8): C07K7/56C07K1/107
Inventor 胡海峰闵涛玲朱宝泉
Owner SHANGHAI INST OF PHARMA IND
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