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Chiral paramagnetic probe using 1,4,7,10-tetraazacyclododecane as skeleton

A tetraazine heterocycle and dodecane technology, applied in the field of chiral paramagnetic probes, can solve problems such as increasing the complexity of experiments and protein sample precipitation

Inactive Publication Date: 2015-05-06
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Compared with the commonly used disulfide bond connection, the triazole ring has better rigidity and chemical stability, but this reaction needs to be carried out under anaerobic conditions, which increases the complexity of the experiment, and the catalyst Cu(I) will lead to protein sample precipitation

Method used

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  • Chiral paramagnetic probe using 1,4,7,10-tetraazacyclododecane as skeleton
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  • Chiral paramagnetic probe using 1,4,7,10-tetraazacyclododecane as skeleton

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Embodiment

[0052] A chiral paramagnetic probe with a skeleton of 1,4,7,10-tetraazacyclododecane, its chemical name is 1,4,7,10-tetraazacyclododecane-1- (2-Methyl-4-phenylsulfonyl-6-methylene)pyridine-2,3,4-tri(S)-propionic acid anion-Tm 3+ Complexes, the chemical formula is C 30 h 40 N 5 o 8 STm, the chemical structural formula is:

[0053] ,

[0054] Its preparation method is as image 3 As shown, the steps are as follows:

[0055] 1) Synthesis of 2,6-lutidine nitrogen oxide, that is, the compound in the route 2

[0056] Mix 2,6-lutidine, glacial acetic acid, and 30wt% hydrogen peroxide in a volume ratio of 15:80:25, keeping 80 o C is heated and stirred under reflux for 4-12h until the conversion of the raw materials is complete, the resulting mixture is concentrated under reduced pressure to one-third and then poured into the ice-water mixture, the amount of 2,6-lutidine and ice-water mixture in the ice-water mixture The ratio is 15.0mL: 100g, then the system is adjusted to...

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Abstract

The invention relates to a chiral paramagnetic probe using 1,4,7,10-tetraazacyclododecane as a skeleton. The chiral paramagnetic probe has the chemical name of 1,4,7,10-tetraazacyclododecane-1-(2-methyl-4-phenylsulfonyl-6-methylene)pyridine-2,3,4-tri(S)-propionic acid anion-Tm3 + complex, the chemical formula of C30H40N5O8STm, and the chemical structural formula as shown in the description. The chiral paramagnetic probe provided by the invention has the advantages of 1) specific chirality, single conformation, only a set of peaks in a spectrogram and high sensitivity; 2) high chemical selectivity; 3) electric neutrality and small impact on macromolecules; 4) good water solubility, more coordination sites, strong stability and high denticity; 5) extremely strong rigidity and good fixation effect on macromolecules; 6) performing of intracellular measurement due to the connection between the probe and a protein through stable thioether bonds. The advantages have an important promotion effect of the chiral paramagnetic probe on the paramagnetic study of proteins.

Description

technical field [0001] The invention belongs to high-performance probes in chemical biology research, in particular to a chiral paramagnetic probe with 1,4,7,10-tetraazacyclododecane (cyclen) as the skeleton. Background technique [0002] The spatial structure of proteins is the basis of their biological functions. Due to its unique properties, nuclear magnetic resonance under the paramagnetic effect has played an increasingly powerful role in the study of the structure and function of biological macromolecules (such as proteins, DNA, RNA, etc.) in recent years; the paramagnetic effect can provide other techniques Long-range structural information of macromolecules that is difficult to obtain by means; functionalized paramagnetic tags are one of the most important technical means for modifying proteins in paramagnetic technology. [0003] The quality of the paramagnetic label plays a decisive role in the study of the structure and dynamics of biological macromolecules usin...

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Application Information

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IPC IPC(8): C07D401/06G01N24/10
Inventor 苏循成杨峰赵宇
Owner NANKAI UNIV
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