Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing fatty acyl cyclic depsipeptide compounds by solid-phase synthesis

The technology of a fatty acyl cyclic ester and a synthesis method is applied in the field of solid-phase synthesis to prepare fatty acyl cyclic ester peptide compounds, which can solve the problems of incomplete esterification of fatty acyl cyclic ester peptides, difficult cyclization and the like, and achieves high synthetic yield, simple method effect

Inactive Publication Date: 2011-04-20
NORTHWESTERN POLYTECHNICAL UNIV
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to avoid the deficiencies of the prior art, the present invention proposes a method for preparing aliphatic acylcyclic ester peptide compounds by solid phase synthesis. Incomplete esterification and difficulty in cyclization

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
  • Method for preparing fatty acyl cyclic depsipeptide compounds by solid-phase synthesis
  • Method for preparing fatty acyl cyclic depsipeptide compounds by solid-phase synthesis
  • Method for preparing fatty acyl cyclic depsipeptide compounds by solid-phase synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] 1.1 Solid-phase synthesis of linear part of fatty acylcyclic ester peptide

[0072] Weigh 50mg of Wang resin (0.2-0.3mmol / g) onto the empty Bio-Spin column, add dichloromethane, fully swell the resin for 0.5-1.0 hours, drain and wash twice with DMF. Take 112mg of Fmoc-Asp-ODmab and 24mg of HOBT in a 1.5ml centrifuge tube, add 1ml of DMF, put it on a rotary mixer and rotate it to dissolve for 10 minutes, then add the pre-reacted solution into the resin, and finally add 27ul DIC to react for 3 hours , washed with DMF for more than three times, drained, added 1ml of 20% pyridine in DMF, reacted twice for 15 minutes, and washed with DMF for more than three times. At this point, the first amino acid, Asp, has been attached to the resin.

[0073] In the same way, Fmoc-Pro-OH, FmocPro-OH, Fmoc-Ser(Trt)-OH, Fmoc-Arg(Pbf)-OH are connected in turn in the same way. After the protection is removed, the reaction conditions agreed to connect the fatty acid RCOOH. After the connectio...

Embodiment 2

[0080] Example 2 attached image 3 The reaction conditions:

[0081] R is a fatty acid, X=O (king resin) or NH (amino resin); a. HOBT / DIC, 3h; b. 20% piperidine (DMF, 15min), 2 times; HOBT / DIC, 2h; repeated connection; c. RCOOH / HOBT / DIC, 3h; d. 1% TFA, 5% TIS (DCM), 3min, 3 times; e. HOBT, DMAP, DCC; f. 20% piperidine (DMF), 15min, 2 times ;g.2%N 2 h 4 (DMF), 2min, 3 times; h.PYBOP / HOBT / DIEA / NMP, 48h; i.TFA / TIS / phenol / H 2 O(95 / 1 / 2 / 2), 3h.

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 relates to a method for preparing fatty acyl cyclic depsipeptide compounds by solid-phase synthesis, which comprises the following steps of: adding amino resin from which fluorenl methoxy carbonyl (Fmoc) is removed, Fmoc-Asp-Odmab, an active agent and straight-chain polypeptide serving as a shrinking agent into a reactor; adding a detritylation reagent into the reactor to immerse a reactant, performing a reaction, and connecting side chain amino acid by an active ester method to obtain a protected cyclization precursor compound; adding a fluorenl methoxy carbonyl removing reagent into the resin for reacting, and washing the resin by using N,N-dimethylformamide; and adding a cyclization agent into the resin to obtain cyclic decapeptide products. By the method, the compounds and analogues thereof are synthesized successfully. The method is simple and high in synthesis yield, and is suitable for synthesizing cyclic depsipeptide with the similar structure.

Description

technical field [0001] The invention relates to a method for solid-phase synthesis of aliphatic acyl-cyclic ester peptide compounds, in particular to methods for selection of starting amino acids, esterification reaction and cyclization reaction. Background technique [0002] In recent years, the problem of antibiotic resistance has become more and more serious, and the need for new antibiotics has become more and more urgent. Antimicrobial peptide antibiotics are a large class of non-specific immune compounds with significant anti-infective activity. Among them, the cyclic lipopeptide antimicrobial peptides are the most eye-catching. As in September 2003, Daptomyhcin for injection approved by the U.S. FDA is exactly a kind of cyclic lipopeptide antibiotics. Its cyclic lipopeptide part is composed of ten It consists of two amino acids with a n-decanoic acid in the side chain. It can be used to treat skin and soft tissue infections and has good results against methicillin-r...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/64C07K1/08C07K1/04
Inventor 钦传光张瑞洁王秋雨任锦李洋牛卫宁徐春兰尚晓娅
Owner NORTHWESTERN POLYTECHNICAL UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com