Synthetic method of 3-acetylpyridine adenine dinucleotide

A technology of acetylpyridine adenine and adenine nucleoside, which is applied in the field of synthesis of 3-acetylpyridine adenine dinucleotide, can solve the problems of high cost and product enzymatic hydrolysis, and achieve low total cost and high product yield , cheap effect

Inactive Publication Date: 2014-02-26
BEIJING LEADMAN BIOCHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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Method used

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  • Synthetic method of 3-acetylpyridine adenine dinucleotide

Examples

Experimental program
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Embodiment 15-T

[0038] Example 15-Synthesis of Tr-D-Ribose (Compound 1).

[0039] Add 15.0g of D-ribose to a 250ml three-necked flask, add 100ml of anhydrous pyridine, and start stirring. Add 27.8 g of triphenylchloromethane. Heat to 75°C, stir and react for 4 hours. Most of the pyridine was distilled off under reduced pressure, then stripped with toluene three times, and dried to obtain a brown syrupy product. Then dissolve with 200ml chloroform, and wash three times with ice water and saturated brine in turn. The organic phase was dried with anhydrous magnesium sulfate, filtered, spin-dried, and recrystallized from ethanol to obtain 39.4 g of product. It is 5-Tr-D-ribose.

[0040] LC-MS: [M+Na] + =415. HNMR (MeOH-d4): δ: 7.605-7.104 (m, 15H); 6.260 (d, 1H); 5.832 (d, 1H); 5.201 (d, 1H); 5.006 (d, 1H) ppm.

Embodiment 2

[0041] Example 2: Synthesis of 5-Tr-1-amino-D-ribose (Compound 2).

[0042] Dissolve 39.4g 5-Tr-D-ribose in 200ml anhydrous methanol, place it in a constant temperature and low temperature water bath, and keep it at 0°C. Under stirring, dry ammonia gas was continuously introduced. After 20 hours, the detected raw material disappeared and it was almost quantitatively converted into 5-Tr-1-amino-D-ribose. 39.2 g of yellow solid is obtained, which is the product.

[0043] LC-MS: [M+H] + =392. HNMR (MeOH-d4): δ: 7.523-7.078 (m, 15H); 5.891 (d, 1H); 5.755 (d, 1H); 4.568 (d, 1H); 4.306 (d, 1H) ppm.

Embodiment 3

[0044] Example 3: Synthesis of 3-acetylpyridine-5-Tr-α-D-nucleoside (compound 3).

[0045] At room temperature, add 50ml of anhydrous methanol to a 250ml three-necked flask, and add 6.0g of 3-acetylpyridine dropwise with stirring. 11.6g of trimethylsilyl trifluoromethanesulfonate (TMSOTf) was slowly added dropwise. After half an hour, a methanol solution of 5-Tr-1-amino-D-ribose was added (19.6 g of 5-Tr-1-amino-D-ribose dissolved in 50 ml of methanol). After the addition is complete, stir at room temperature for 5 hours. The solvent was evaporated under reduced pressure. Dissolve with as little volume of methanol as possible, add anhydrous ether slowly, and a solid will precipitate. Filter and dry to obtain crude product. Column chromatography eluted with dichloromethane and methanol system to obtain 9.65 g of 3-acetylpyridine-5-Tr-α-D-nucleoside.

[0046] LC-MS: [M] + =496 (after deducting trifluoromethanesulfonate). HNMR (DMSO-d6): δ: 9.472 (s, 1H); 9.387 (s, 1H); 9.165 (d...

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Abstract

The invention discloses a chemical synthesis method of 3-acetylpyridine adenine dinucleotide, comprising the following steps: (1) D-ribose is used as a starting material to prepare monophosphate-3-acetylpyridine-alpha-D-nucleoside; (2) adenosine is used as a main raw material to prepare morpholine adenosine monophosphate; and (3) a docking reaction between morpholine adenosine monophosphate and monophosphate-3-acetylpyridine-alpha-D-nucleoside is carried out to prepare 3-acetylpyridine adenine dinucleotide. According to the chemical synthesis method, a commercial industrial product D-ribose is used as the starting raw material; any enzyme is not used during the preparation process of an intermediate; price of raw materials is low and the raw materials are easy to purchase; and production cost of the product is reduced greatly. In addition, by the chemical synthesis method, yield of the product is high, and total yield of the reaction is 4.2% and is remarkably higher than product yield of a present biosynthesis method.

Description

Technical field [0001] The invention relates to a method for synthesizing purine derivatives, in particular to a method for chemical synthesis of 3-acetylpyridine adenine dinucleotide, and belongs to the field of synthesis of 3-acetylpyridine adenine dinucleotide. Background technique [0002] 3-Acetylpyridine adenine dinucleotide can be widely used in various fields as a raw material for biochemical reagents. The first reported method for the synthesis of 3-acetylpyridine adenine dinucleotide was a 1956 document (The Journal of Biological Chemistry, 1956, 221, 823-832.), which disclosed the 3-acetylpyridine gland The synthetic method of purine dinucleotide belongs to the biosynthetic method. Since then, Nathan O.Kaplan et al. disclosed a biosynthetic method for preparing 3-acetylpyridine adenine dinucleotide from nicotinamide adenine dinucleotide (NAD), which uses NAD as a raw material and uses pig brain The glycoside transfer effect of NPD enzyme partially converts nicotinami...

Claims

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Application Information

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IPC IPC(8): C07H21/02C07H1/00
Inventor 不公告发明人
Owner BEIJING LEADMAN BIOCHEM
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