Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the post-processing is not handled properly, it is easy to cause enzymatic hydrolysis of the product
Raw material NAD and various enzymes are expensive

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method of 3-acetylpyridine adenine dinucleotide

Examples

Experimental program
Comparison scheme
Effect test

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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07H21/02C07H1/00
Inventor 不公告发明人
Owner BEIJING LEADMAN BIOCHEM
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com