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Prosthetic linking arm, its synthesis method and the synthesis method of diubiquitin

A synthesis method and linker technology, which is applied in the field of prosthetic linker, its synthesis method and the synthesis of diubiquitin, can solve the problems of large prosthetic group hindrance, harsh removal conditions, large steric hindrance, etc. In addition to the effects of mild conditions, high chemical connection efficiency, and avoidance of non-denaturing conditions

Active Publication Date: 2019-10-22
UNIV OF SCI & TECH OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prosthetic group has cumbersome synthesis steps, large steric hindrance, and harsh removal conditions
Tom W. Muir and colleagues found that the light-sensitive prosthetic group is used for the ubiquitination of histones, but the prosthetic group has large steric hindrance and low efficiency of chemical ligation reaction

Method used

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  • Prosthetic linking arm, its synthesis method and the synthesis method of diubiquitin
  • Prosthetic linking arm, its synthesis method and the synthesis method of diubiquitin
  • Prosthetic linking arm, its synthesis method and the synthesis method of diubiquitin

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preparation example Construction

[0045] The embodiment of the present invention discloses a synthesis method of a prosthetic linking arm having a structure of formula (I) applied to the preparation of diubiquitin, comprising the following steps:

[0046] A), reacting the compound having the structure of formula (II) and the compound having the structure of formula (III) under the catalysis of a basic compound to obtain the compound having the structure of formula (IV);

[0047] Under the action of a catalyst, the compound with the structure of formula (IV) is reacted in methanol to obtain the compound with the structure of formula (V);

[0048] reacting N-hydroxyphthalimide with a compound of formula (VI) under the action of a catalyst to obtain a compound of formula (VII);

[0049] B), under the action of a catalyst, the compound having the structure of formula (V) is reacted with the compound having the structure of formula (VII) to obtain the compound having the structure of formula (VIII);

[0050] C) reac...

Embodiment 1

[0079] Embodiment 1: Synthesis of novel prosthetic group linking arm O-(2-((2-nitrobenzyl) mercapto) ethoxy) hydroxylamine

[0080] Compound IV1: Weigh 4.04g of o-nitrobenzyl chloride (23.6mmol) and 3.86g of potassium carbonate and place them in a round-bottomed flask respectively, add 24ml and 48ml of tetrahydrofuran solution for dissolution, and add 2ml of thioacetic acid (30.5mmol); after 30 minutes, the tetrahydrofuran solution containing o-nitrobenzyl chloride was added to the above solution for reaction, and the reaction progress was monitored by TLC. Evaporator to remove volatile tetrahydrofuran, dissolve the solid with an appropriate amount of dichloromethane, then extract twice with saturated sodium bicarbonate solution and water, collect the organic phase, dry with anhydrous sodium sulfate, filter, spin dry, and weigh the compound IV1 o-nitrobenzyl thioacetate 5.87g (yellow liquid), directly proceed to the next reaction. Such as figure 1 as shown, figure 1 The pro...

Embodiment 2

[0088] The preparation method is the same as in Example 1, except that in the step of preparing compound IV1, the solvent is water and acetonitrile with a volume ratio of 2:1.

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Abstract

The invention provides a process for synthesizing a prosthetic group linking arm and a method for synthesizing di-ubiquitin by the aid of the prosthetic group linking arm. The prosthetic group linkingarm, the process and the method have the advantages that the prosthetic group linking arm is easy to synthesize and store and stable in chemical property; the prosthetic group linking arm is high inchemical linking efficiency in procedures for synthesizing the di-ubiquitin by the aid of the novel prosthetic group linking arm, and protein linking can be carried out under physiological conditions;the novel prosthetic group linking arm can be removed under mild conditions, and accordingly harsh non-denaturation conditions in prosthetic group removal procedures for chemical synthetic protein ubiquitination at present can be omitted.

Description

technical field [0001] The invention relates to the technical field of synthesis of diubiquitin, in particular to a prosthetic linking arm, a synthesis method thereof and a synthesis method of diubiquitin. Background technique [0002] Ubiquitination is a very important protein post-translational modification, which is involved in the regulation of almost all cellular processes in eukaryotes, including cell cycle, transcriptional activation, and protein degradation. Ubiquitin itself can be used as a substrate to form polyubiquitin chains with different chain connection types and chain lengths on the basis of 8 sites (M1, K6, K11, K27, K29, K33, K48 and K63). [0003] At present, there are many methods (such as total protein synthesis method, enzymatic method, gene coding method, etc.) to synthesize polyubiquitin chains. The total protein synthesis method is limited by the cumbersome chemical synthesis steps and the difficulty in obtaining it in biological laboratories. The...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/20C07C323/12C07K14/00C07K1/06C07K1/02
Inventor 黄健丰石景储国超
Owner UNIV OF SCI & TECH OF CHINA
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