Synthetic method of decarboxylated carnosine

A technology of decarboxylated carnosine and a synthesis method, which is applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of large environmental pollution, strong catalyst toxicity, and many process steps, achieve high purity and total yield, and reduce the cost of protective groups. , the effect of simple operation

Inactive Publication Date: 2020-04-10
东莞市维琪科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The traditional production of decarboxylated carnosine has problems such as many process steps, strong catalyst toxicity, and large environmental pollution. Therefore, the development of a simple process, less by-products, high yield, high purity of the finished product, low preparation cost, and less environmental pollution is suitable for large-scale industrialization. The synthetic method of production is of great significance

Method used

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  • Synthetic method of decarboxylated carnosine
  • Synthetic method of decarboxylated carnosine
  • Synthetic method of decarboxylated carnosine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1Bo

[0031] Example 1 Synthesis of Boc-β-Ala-OSU

[0032] Prepare a 3L serum bottle and wash it twice with 200mL DCM.

[0033] Add 189.21g Boc-β-Ala-OH and 138.1g HOSU into the serum bottle, and add 800mL DCM to dissolve. Ice bath, make the system temperature drop below 10℃.

[0034] In addition, 230.03g EDC.HCl was dissolved in 1L DCM, and the resulting solution was slowly added dropwise to the above system.

[0035] After 6 hours of reaction, 11.51g HOSU and 19.17g DEC.HCl were added, and samples were taken after 12 hours of reaction, and the reaction was completed after detection by thin layer chromatography. The raw materials disappeared completely.

[0036] The insoluble matter in the reaction system was removed by filtration, washed with ice water, and extracted with ethyl acetate. The extract was treated with a rotary evaporator and spin-dried to obtain Boc-β-Ala-OSU for use.

Embodiment 2B

[0037] Example 2 Synthesis of Boc-β-Ala-histamine

[0038] Prepare a 5L serum bottle and wash it twice with 200mL DCM.

[0039] Mix 193.3g histamine dihydrochloride, 420g NaHCO 3 Add to the serum bottle, add 600mL ACN and 600mL water, and stir thoroughly.

[0040] In addition, the intermediate 286.3g Boc-β-Ala-OSU from the previous step was dissolved in 1500mL ACN and slowly added to the above system. After reaction for 2h, the reaction was completed after the raw material point disappeared completely after detection by thin layer chromatography.

[0041] After filtration, the filtrate was treated with a rotary evaporator to remove ACN, and a large amount of solids were precipitated. After being drained, Boc-β-Ala-histamine was obtained for use.

Embodiment 3

[0042] Example 3 Deprotection

[0043] Add the solid from the previous step to EA, stir well, add HCl / methyl acetate, after 40 minutes of reaction, remove the liquid by suction filtration, and wash the solid with EA foam 3 times. The finished product decarboxylized carnosine is obtained by draining, with a purity of 99.2% and a total yield of 69.6%.

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Abstract

The invention discloses a synthetic method of decarboxylated carnosine, and belongs to the technical field of short peptide synthesis. The synthetic method comprises the steps: Boc-beta-Ala-OH reactswith HOSU to obtain Boc-beta-Ala-OSU, Boc-beta-Ala-OSU reacts with histamine dihydrochloride and NaHCO3 to obtain Boc-beta-Ala-histamine, and finally, a Boc protecting group is removed to obtain the finished product decarboxylated carnosine. According to the synthetic method of the decarboxylated carnosine, the adopted raw material histamine side chain does not need to be protected, the reaction steps are reduced, the cost of the protecting group is reduced, the operation is simple, byproducts are few, the purity and the total yield are high, and the synthetic method is suitable for industriallarge-scale production.

Description

Technical field [0001] The invention belongs to the technical field of short peptide synthesis, and relates to a synthesis method of decarboxyl carnosine. Background technique [0002] Many products with significant whitening and anti-freckle effects contain some prohibited substances such as lead-containing mercury, hormones, or some irritating side effects such as hydroquinone, etc., whose toxic side effects are significant and their use is restricted. At present, bears are widely used and safe in the market. Fruit glycosides, kojic acid, vitamin C derivatives and some traditional Chinese medicine extracts, etc., but their stability is poor and the mechanism of action remains to be studied. On the basis of improving the lack of existing whitening ingredients, researchers continue to develop new whitening and freckles removing products. The development of new products combining biologically active peptides and modern high-tech technology is a hot spot. Polypeptide is a natural ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64
CPCC07D233/64Y02P20/55
Inventor 丁文锋孙新林
Owner 东莞市维琪科技有限公司
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