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Chemical complete synthesis method for 22nd natural amino acid-pyrrolysine

A technology of pyrrolysine and natural amino acid, applied in the directions of organic chemistry, bulk chemical production, etc., can solve the problems of instability and change of imine bonds, and achieve the effects of simple reaction device, low operating cost, and not easy to deteriorate

Inactive Publication Date: 2010-05-19
EAST CHINA UNIV OF SCI & TECH
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Problems solved by technology

For example, premature exposure of unstable imine bonds to subsequent reactions can easily lead to changes in imine bonds due to instability

Method used

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  • Chemical complete synthesis method for 22nd natural amino acid-pyrrolysine
  • Chemical complete synthesis method for 22nd natural amino acid-pyrrolysine

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Embodiment 1

[0043] 1. Methyl (E)-2-(2,2-dimethylpropyleneamino)acetate (1)

[0044] Add 0.740g glycine methyl ester hydrochloride (0.578mmol), 8ml benzene, 0.507g 2,2-dimethylpropanal (0.578mmol, 0.64ml) into a 25ml flask, then drop into 0.584g triethylamine (0.578 mmol), start heating, and reflux for 1h. After the reaction, washed with water, extracted, dried, and distilled under reduced pressure to obtain 0.81 g of oily liquid compound (E)-2-(2,2-dimethylpropyleneamino)acetate methyl ester with a yield of 90%.

[0045] 1 H-NMR (500Hz, CDCl 3 ): 1 (9H, s), 3.66 (3H, s), 4.07 (2H, s), 7.46 (1H, s).

[0046] Two, 2-(2,2-dimethylpropyleneamino)-3-methyl ethyl glutarate (2)

[0047] Add 0.81g of compound 1 (0.517mmol) (prepared in step 1), 22ml of anhydrous THF into a 50ml flask, add 0.494g of lithium bromide (0.569mmol), and then add 0.589g of ethyl crotonate (0.517mmol, 0.64 ml), 0.786g 1,8-diazabicyclo(5,4,0)-7-undecene (0.517mmol, 0.77ml) was added, and the reaction was stirred at r...

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Abstract

The invention relates to a chemical complete synthesis method for 22nd natural amino acid-pyrrolysine. 2,2-dimethyl propionaldehyde reacts with glycine methyl ester hydrochloride to form (E)-2-(2,2-dimethyl propylidene-amino) methylacetate, and the product generates Michael addition with olefine aldehyde by the catalysis of DBU and then carries out hydrolysis to obtain a pyrrole ring. After being vulcanized and methylated, the pyrrole ring is condensed with a derivative of lysine, and finally sulfomethyl is removed to obtain the pyrrolysine. The invention has cheap and easily acquired chemical raw materials, wide source, low cost, mild and easily controlled reaction condition, simple reaction device and low operation cost; by adopting various protecting groups, all intermediate compounds are more stable and are difficult for modification; and all reactions are mature and are in fixed quantity, and the yield is higher.

Description

【Technical field】 [0001] The invention relates to the technical field of fine chemicals, in particular, it is a chemical total synthesis method of the twenty-second natural amino acid-pyrrolysine. 【Background technique】 [0002] In 2002, two research teams at Ohio State University reported that they identified the world's 22nd amino acid encoded by a genetic gene. After confirming the discovery of the novel twenty-second natural amino acid, the confirmation of the structure of the amino acid started immediately. It was found that it is composed of two parts of lysine and (4R,5R)-4-methyl-pyrrole ring-5-carboxyl. Its chemical structure is as follows: [0003] [0004] pyrrolysine [0005] Due to the great significance of pyrrolysine in the study of gene coding and in the field of life sciences, the research on pyrrolysine has attracted the attention of many scientists. [0006] Joseph A. Krzycki's colleague Michael K. Chan has been engaged in the research on the artifi...

Claims

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Application Information

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IPC IPC(8): C07D207/22
CPCY02P20/55
Inventor 罗晓燕高嘉斌岳伟民段梅莉周宇峰李鑫孙琳
Owner EAST CHINA UNIV OF SCI & TECH
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