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
View PDF6 Cites 4 Cited by
  • 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-product

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
  • Preparation method of deoxy analog of Echinocandin B
  • Preparation method of deoxy analog of Echinocandin B
  • Preparation method of deoxy analog of Echinocandin B

Examples

Experimental program
Comparison scheme
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.

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 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

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