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Daptomycin analog and full solid phase synthesis preparation method thereof

A technology of daptomycin and analogues, applied in the field of all-solid-phase synthesis, can solve the problems of cumbersome steps, high cost, energy and time consumption, etc.

Inactive Publication Date: 2010-04-21
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the problems of cumbersome steps, energy consumption, time-consuming and high cost in the existing methods

Method used

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  • Daptomycin analog and full solid phase synthesis preparation method thereof
  • Daptomycin analog and full solid phase synthesis preparation method thereof
  • Daptomycin analog and full solid phase synthesis preparation method thereof

Examples

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Embodiment Construction

[0086] Now in conjunction with embodiment, accompanying drawing, the present invention will be further described:

[0087] Example of Synthetic Daptomycin Analogs (1): AA 1 Select Fmoc-Glu-ODmab, AA 9 Choose Fmoc-L-Ser(Trt)-OH, choose C for R 10 h 20 o 2 (n-capric acid). The sequence is:

[0088]

[0089] Its structure diagram is shown in the appendix of the manual Figure 4

[0090] Concrete synthetic steps:

[0091] 1. Prepare the solution

[0092] 1) Remove Fmoc protecting group (Deprotection) solution

[0093] 20% piperidine in DMF, V / V

[0094] 2) Kaiser Test solution

[0095] A.5% ninhydrin ethanol solution, W / V

[0096] B. 80% phenol ethanol solution, W / V

[0097] C.2% 1mmol / L potassium cyanide pyridine solution, V / V

[0098] 2. Resin activation

[0099] Accurately weigh 100mg Rink Amide-AM Resin (0.28mmol / g, 100-200mesh) into a 2mL Bio Spin empty column, add 1mL chloroform (CHCl 3 ) to fully mix, place on a rotary mixer and soak for more than 30 minu...

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Abstract

The invention relates to a daptomycin analog and a full solid phase synthesis preparation method thereof. The full solid phase synthesis preparation method is technically characterized by comprising the steps of: linking a first Fmoc amino acid (Alpha-carboxyl thereof is protected by a selected group) to a solid phase resin carrier, wherein the side chain of the first Fmoc amino acid is provided with carboxyl; continuing to sequentially link 7 Fmoc amino acids, and sequentially removing Fmoc; linking a ninth Fmoc amino acid and removing Fmoc, wherein the side chain of the ninth Fmoc amino acid is provided with carboxyl (sulfydryl or amino) and the ninth Fmoc amino acid is protected by a selective group; continuing to sequentially link the subsequent 3 Fmoc amino acids and removing Fmoc; after linking fatty acid, selectively removing the protective group on the carboxyl (sulfydryl or amino) of the side chain of the ninth amino acid, then reacting with the carboxyl of the last Fmoc amino acid and removing Fmoc; after removing the protective group of the Alpha-carboxyl of the first amino acid, carrying out the cyclization on solid phase resin directly; and at last, cutting the product from the resin, and obtaining the product through the precipitation of cold ethyl ether.

Description

technical field [0001] The invention relates to a daptomycin analogue and a preparation method for all-solid-phase synthesis thereof, and belongs to the molecular design strategy of the antibiotic daptomycin (Daptomycin) and its analogue and a full-solid-phase synthesis method. Background technique [0002] With the continuous emergence of highly pathogenic and drug-resistant bacteria, such as MRSA, VRE, and PRSP, the clinical demand for new antibiotics is becoming more and more urgent, and daptomycin has successfully dealt with the above-mentioned drug-resistant bacteria and has good curative effect and simple preparation , Toxicity and side effects are small, making it a hot spot in the research of new antibiotics. Its chemical structure and mechanism of action are different from those of existing antibiotics, and it is the only antibiotic of a new structural class that has been used clinically in the past 40 years. [0003] Daptomycin can be used as a class of small-mole...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/08C07K7/06C07K7/64C07K7/50C07K1/06C07K1/04
CPCY02P20/55
Inventor 钦传光任锦牛卫宁丁焰王秋雨徐春兰尚晓娅
Owner NORTHWESTERN POLYTECHNICAL UNIV
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