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A kind of solid phase synthesis method of cyclic lipopeptide orfamide A

A technology of solid-phase synthesis and cyclic ester peptides, which is applied to the preparation methods of peptides, chemical instruments and methods, peptides, etc., and can solve the problems that there is no artificial synthesis of OrfamideA.

Inactive Publication Date: 2016-05-04
HYBIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, at present, the cyclic ester peptide OrfamideA can only be obtained by biological separation, and there is no report on the artificial synthesis of OrfamideA.

Method used

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  • A kind of solid phase synthesis method of cyclic lipopeptide orfamide A
  • A kind of solid phase synthesis method of cyclic lipopeptide orfamide A
  • A kind of solid phase synthesis method of cyclic lipopeptide orfamide A

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1: the preparation of the Fmoc-D-Ser(Resin)-OAll whose degree of substitution is 0.2mmol / g

[0027] Weigh 100g (100mmol) of DHPHM resin with a substitution degree of 1.0mmol / g, add it to the solid-phase reaction column, wash it twice with DCE, and swell the resin with DCE for 60 minutes, take 21.9g Fmoc-D-Ser-OAll (60mmol) and 7.5gPPTS (30mmol) were dissolved in 200ml DCM solution, added to the resin, and reacted at 80°C for 5h under the protection of nitrogen. Cool and filter, wash with DMF, DCM, and Hexane three times, and dry. The detected substitution degree is 0.205mmol / g.

Embodiment 2

[0028] Embodiment 2: the preparation of the Fmoc-D-Ser(Resin)-OAll whose degree of substitution is 0.5mmol / g

[0029] Weigh 100g (100mmol) of DHPHM resin with a substitution degree of 1.0mmol / g, add it to a solid-phase reaction column, wash it twice with DCE, and swell the resin with DCE for 60 minutes, take 54.7g Fmoc-D-Ser-OAll (150mmol) and 18.8gPPTS (75mmol) were dissolved in 200ml DCM solution, added to the resin, and reacted at 80°C for 5h under the protection of nitrogen. Cool and filter, wash with DMF, DCM, and Hexane three times, and dry. The detection degree of substitution is 0.500 mmol / g.

Embodiment 3

[0030] Embodiment 3: the preparation of the Fmoc-D-Ser(Resin)-OAll that the degree of substitution is 0.3mmol / g

[0031] Weigh 100g (100mmol) of DHPHM resin with a substitution degree of 1.0mmol / g, add it to the solid-phase reaction column, wash it twice with DCE, and swell the resin with DCE for 60 minutes, take 32.8g Fmoc-D-Ser-OAll (90mmol) and 11.3gPPTS (45mmol) were dissolved in 200ml DCM solution, added to the resin, and reacted at 80°C for 5h under the protection of nitrogen. After cooling and filtering, washing with DMF, DCM and Hexane three times respectively, and drying, the detected substitution degree was 0.302 mmol / g.

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Abstract

The invention belongs to the technical field of pharmaceutical synthesis, and discloses a pure solid-phase synthetic method of Halipeptin Orfamide A. The solid-phase synthetic method is used for efficient and mass production of the Halipeptin orfamide A.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a solid-phase synthesis method of cyclic lipopeptide OrfamideA. Background technique [0002] OrfamideA is a major component of a cyclolipopeptide reported in 2007 produced by Pseudomonas fluorescens. Its structure is shown in the following formula: [0003] [0004] W.H.Gerwick et al. predicted that some special precursors were required in the biosynthesis of Orfamide A through bioinformatics methods, and fed the microorganisms with isotope-labeled precursor substances, and then successfully obtained the compound orfamideA by isotope-labeled isolation and detection methods. On research, Orfamide appears to be a selective antifungal agent. Uniquely, OrfamideA is able to dissolve zoospores of Oomycetes fungi and the sudden oak death pathogen causing sudden oak death. Moreover, Orfamide A can have a profound effect on the colony movement of bacteria on the agar surface...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/20C07K1/06C07K1/04
CPCY02P20/55
Inventor 宓鹏程潘俊锋马亚平袁建成
Owner HYBIO PHARMA
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