A kind of synthetic method of antibacterial activity cyclic hexapeptide thermoactinoamide A

A synthesis method and technology of antibacterial activity, applied in the field of synthesis of antibacterial active cyclohexapeptide Thermoactinoamide A, can solve the problem that the output cannot meet the practical application and other problems

Inactive Publication Date: 2020-09-04
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many cyclic peptide structures isolated in nature, their yield is far from meeting practical applications, so artificial synthesis of cyclic peptides is one of the hottest topics now

Method used

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  • A kind of synthetic method of antibacterial activity cyclic hexapeptide thermoactinoamide A
  • A kind of synthetic method of antibacterial activity cyclic hexapeptide thermoactinoamide A
  • A kind of synthetic method of antibacterial activity cyclic hexapeptide thermoactinoamide A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: Resin complex of fluorenylmethoxycarbonyl isoleucine (Fmoc-D-allo-Ile-resin)

[0049] Take 1.1 g of 2-chlorotriphenylmethyl chloride resin (loading capacity: 0.94 mmol / g) in a 100 ml peptide synthesis tube, add 20 ml of dichloromethane (DCM) to swell for 30 minutes. The filtrate was drained, and fluorenylmethoxycarbonyl D-isoleucine (Fmoc-D-allo-Ile-OH, 0.5g, 1.4mmol) and diisopropylethylamine (DIEA , 463uL, 2.8mmol), stirred or shaken for 4 hours, the filtrate was drained, washed with dichloromethane (DCM, 10ml) and dimethylformamide (DMF, 10ml) alternately for 3 times each, and the filtrate was drained to obtain Fmoc-D-allo-Ile-resin.

Embodiment 2

[0050] Example 2: Residual site blocking on resin

[0051] A methanol (MeOH, 18ml) solution with a volume fraction of 10% diisopropylethylamine (DIEA, 2ml) was added to the product of Example 1, stirred or shaken for 30min, the filtrate was drained, and 10ml of DCM was used to , DMF alternately washed 3 times, and the filtrate was drained.

Embodiment 3

[0052] Example 3: Protected linear dipeptide-resin complex (Fmoc-Leu-D-allo-Ile-resin)

[0053] (1) Add the DMF solution of the 20% piperidine of 10ml in the product of embodiment 2, react for 10 minutes, wash 3 times alternately with DCM, DMF respectively of 10ml, drain the filtrate, for more thorough removal of fluorenylmethoxy For carbonyl (Fmoc) protection, the steps before step (1) can be repeated again, that is, add 10 ml of 20% piperidine in DMF solution to the filter residue after the filtrate is drained, react for 10 minutes, and use 10 ml of DCM and DMF respectively Rinse 3 times alternately, drain the filtrate, and complete the deprotection;

[0054] (2) Weigh Fmoc-Leu-OH (Fmoc-Leu-OH, 0.99g, 2.8mmol) and 3-(diethoxy-o-acyloxy)-1,2,3-benzotriazine -4-ketone (DEPBT, 0.84g, 2.8mmol) in a 50ml conical flask, after adding 10ml of DMF to dissolve, then add diisopropylethylamine (DIEA, 0.46ml, 2.8mmol), add step ( 1) The product after draining the filtrate in the medium...

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Abstract

The invention belongs to the field of synthesis of compounds with extensive antibacterial activity, and discloses a synthetic method of an antibacterial active cyclic hexapeptide Thermoactinoamide A.According to the method, a polypeptide solid phase synthesis method is adopted, the synthesis process is simple, the raw material cost is low, and the reaction conditions are mild, wherein for aromatic amino acids and valine, an Oxyma / DIC system is used as a condensing agent, and for aliphatic amino acids especially leucine and isoleucine, a DEPBT / DIEA system is used as a condensing agent; and theyield of the linear cyclic hexapeptide obtained through eight step reactions is 87.11%, the purity is 95% or more, the yield of the cyclic hexapeptide obtained after a cyclization reaction is 85.23%,the purity is 99% or more, and the total yield is 74.24%. According to the method, the obtained product has high purity and high yield, is likely to be in industrialization, and has a very high medical value and a broad market prospect.

Description

technical field [0001] The invention belongs to the field of synthesizing compounds with extensive antibacterial activity, and in particular relates to a synthesis method of a cyclohexapeptide Thermoactinoamide A with antibacterial activity. Background technique [0002] As a marine drug, cyclic peptides have attracted more and more attention from scientists, because cyclic peptides can form new unique structures through the connection of different amino acids and have excellent biological activities, providing important information for the development and research of new drugs. Guidance (Y. Lee et al. Peptides 95(2017) 94–105; Tapeinou A et al. Biopolymers, 2015, 104(5):453-461). Although there are many cyclic peptide structures isolated in nature, their yields are far from enough for practical applications, so the artificial synthesis of cyclic peptides is one of the hottest topics now. [0003] Thermoactinoamide A is a novel cyclic hexapeptide isolated from a bacterial s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/64C07K1/06C07K1/04
CPCC07K7/64Y02P20/55
Inventor 孙月光李杭斌徐石海
Owner JINAN UNIVERSITY
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