Compound Biotin-PEG3-SS-DBCO as well as preparation method and application thereof

A biotin-peg3-ss-dbco and compound technology, applied in the field of chemistry, can solve the problems of small preparation scale, low yield and high cost, and achieve the effects of low cost and simple preparation method

Active Publication Date: 2022-03-01
宜昌博仁凯润药业有限公司
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  • Abstract
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  • Claims
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Problems solved by technology

[0003] As far as the currently published synthetic methods are concerned, all of them require chromatographic purification; at the same time, many materials are required, the cost is high, the preparation scale is small, and the yield is not high

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  • Compound Biotin-PEG3-SS-DBCO as well as preparation method and application thereof
  • Compound Biotin-PEG3-SS-DBCO as well as preparation method and application thereof
  • Compound Biotin-PEG3-SS-DBCO as well as preparation method and application thereof

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preparation example Construction

[0033] The preparation method of the compound Biotin-PEG3-SS-DBCO provided by the embodiments of the present invention comprises the following steps:

[0034] Step 1, the synthesis of compound 2: at room temperature, slowly add 2,2'-dithiodipyridine to the methanol solution of compound 1, after the addition is completed overnight at room temperature, the reaction solution is spin-dried and passed through the column to obtain 7.83g of white solid; step 1 2,2'-dithiodipyridine is 10 g, 45.390 mmol; the compound 1 is 4.91 g, 43.229 mmol; the methanol is 100 ml.

[0035] Step 2, the synthesis of compound 3: slowly add mercaptopropionic acid to the methanol solution of compound 2, after overnight at room temperature, spin dry directly, add 150ml of water, wash the water phase with 200ml DCM several times, and dry the water phase to obtain 8.04g Earthy gray solid; step dimercaptopropionic acid is 4.11g, 38.73mol; the compound 2 is 8.63g, 38.73mol; methanol is 100ml.

[0036]Step 3,...

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Abstract

The invention belongs to the technical field of chemistry, and discloses a compound Biotin-PEG3-SS-DBCO as well as a preparation method and application thereof.The preparation method comprises the following steps: slowly adding 2, 2 '-dithio bipyridine into 2-aminoethanethiol hydrochloride to react to obtain 2-(2-pyridyl disulfide) ethylamine hydrochloride; adding thiohydracrylic acid into the methanol solution of the compound 2 to obtain 3-[(2-aminoethyl) dithio] propionic acid hydrochloride; the preparation method comprises the following steps: slowly adding pentafluorophenol into a dichloromethane solution of dibenzocyclooctyne-carboxyl (compound 4) and EDCI, and then adding a compound 3 and triethylamine to prepare dibenzocyclooctyne-disulfide bond-carboxyl (compound 5); the preparation method comprises the following steps: slowly adding pentafluorophenol into a dichloromethane solution of a compound 5 and EDCI, then adding biotin tripolyethylene glycol amino (a compound 7) and triethylamine to react, and purifying to obtain the compound Biotin-PEG3-SS-DBCO. The preparation method is simple and low in cost.

Description

technical field [0001] The invention belongs to the technical field of chemistry and discloses a compound Biotin-PEG3-SS-DBCO, a preparation method and an application thereof. Background technique [0002] Dibenzoazepine octyne (DBCO or ADIBO) is a strained cyclooctyne, and the second-order reaction rate constant in the commonly used strained cyclooctyne is as high as 0.36M -1 the s -1 (Chem. Commun., 2010, 46, 97–99; Chem. Commun., 2013, 49, 11007). Up to now, reagents containing cyclooctynol, bicyclo[6.1.0]nonyne (BCN), DBCO-COOH, and DBCO-NHS have been widely used in biochemistry, and the reaction principle is collectively referred to as the stacking process promoted by tension (stress). Nitrogen-alkyne cycloaddition reaction (strain-promoted azide-alkyne cycloaddition, referred to as SPAAC), belongs to click chemistry (Huisgen cycloaddition). Its characteristic is that the chemical reaction does not need to be catalyzed by copper ions, and it can be used in protein mo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
CPCC07D495/04Y02P20/55
Inventor 杨锋李志李生祥王建新郑雪静
Owner 宜昌博仁凯润药业有限公司
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