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Lanthionine derivative

一种硫基、化合物的技术，应用在羊毛硫氨酸衍生物领域，能够解决稳定性、气味问题等问题，达到稳定性良好、低成本的效果

Inactive Publication Date: 2014-05-07
AJINOMOTO CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, glutathione contains cysteine, which is a sulfur-containing amino acid, in its molecule, so it has problems in terms of stability, odor, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0179] (Example 1) compound 1 Synthesis

[0180] (Fmoc-L-Cys-Ot-Bu) 2 (N,N'-difluorenylmethoxycarbonyl-L-cystine di-t-butylester, 4.81mmol) was dissolved in tetrahydrofuran (58.5mL) and water (1.5mL). Tributylphosphine (5.28 mmol) was added under ice-cooling to return to room temperature, and stirred for 4 hours. The reaction liquid was cooled, and 10% aqueous citric acid solution (60 mL) was added. The cloudy solution was returned to room temperature, and extracted with ethyl acetate (60 mL). The organic layer was washed with 60 mL of brine, and concentrated to obtain an oily residue. The residue was purified with a silica gel column (n-hexane-ethyl acetate) to obtain the compound as an oil 1 .

[0181] The yield is 97%.

[0182] ESI MS m / z 422.4 (M+Na) +

[0183] 1 H NMR (400MHz, CDCl 3 )δ1.50(9H,s),2.99(2H,m),4.23(1H,t,J=6.8Hz),4.41(2H,m),4.54(1H,m),5.68(1H,d,J =7.2Hz),7.32(2H,m),7.41(2H,t,J=7.2Hz),7.61(2H,d,J=7.6Hz),7.77(2H,d,J=7.2Hz).

[0184] [chemical formu...

Embodiment 2）

[0186] (Example 2) compound 2 Synthesis

[0187] compound 1 (6.04mmol) was dissolved in dimethylformamide (60mL), after adding Boc-iodo-D-Ala-OMe (N-t-butoxycarbonyl-3-iodo-D-alanine methylester) (6.20mmol), adding cerium carbonate ( 6.02 mmol), stirred overnight at room temperature. The reaction solution was cooled, 10% citric acid aqueous solution (50 mL) and water (30 mL) were added, extracted with ethyl acetate (60 mL), and then the aqueous layer was extracted with ethyl acetate (60 mL) again. The organic layers were combined, washed successively with 10% citric acid aqueous solution (50 mL) and brine (50 mL), and the organic layer was concentrated. The obtained oily residue was purified with a silica gel column (n-hexane-ethyl acetate) to obtain the compound as an oil 2 .

[0188] Yield 66%.

[0189] ESI MS m / z 601.2(M+H) +

[0190] 1 H NMR (400MHz, CDCl 3 )δ1.45(9H,s),1.49(9H,s),3.01(4H,m),3.73(3H,s),4.24(1H,t,J=7.2Hz),4.39(2H,d,J =7.2Hz),4.48-4.55(2H,m),5.37(...

Embodiment 3）

[0193] (Example 3) compound 4 Synthesis

[0194] (Step 1) Compound 2 (4.01 mmol) was dissolved in 70 mL of dichloromethane, trifluoroacetic acid (70 mL) was added, stirred at room temperature for 1 hour, and the reaction solution was concentrated to obtain a residue containing 3. Assuming a yield of 100%, it was directly used in the next reaction.

[0195] [chemical formula 20]

[0196]

[0197] (Step 2) Under ice cooling, anhydrous dimethylformamide (60 mL) was added to compound 3 (corresponding to 4.01 mmol) to form a homogeneous liquid, and diisopropylethylamine (8.04 mmol) was added dropwise thereto. After returning to room temperature, carbonylbiimidazole (8.10 mmol) was added, and the mixture was stirred overnight. Under the condition of cooling and stirring, 10% citric acid aqueous solution (50 mL) was added to the reaction solution, and after returning to room temperature, it was extracted with ethyl acetate (100 mL), and the aqueous layer was extracted with ethy...

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PUM

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Abstract

To search a number of variation compounds having a CaSR agonist activity in order to obtain a substance having a more excellent kokumi-imparting function, and more particularly to provide a kokumi-imparting agent, which contains the foregoing substance, and a composite kokumi-imparting agent, which likewise contains the aforementioned substance and another substance having a CaSR agonist activity as well, in combination a kokumi-imparting agent comprises a lanthionine derivative and a composite kokumi-imparting agent comprising the lanthionine derivative and another substance having a CaSR agonist activity.

Description

technical field [0001] The present invention relates to a novel compound exhibiting CaSR agonist activity, a food composition containing the same, and a kokumi-imparting agent. Background technique [0002] In recent years, due to the diversification of dietary life, etc., consumers' requirements for taste have increased. Along with this, there has been an increase in demand for excellent kokumi-imparting agents that can impart "kokumi" that cannot be obtained with only sweet taste. Taste represented by the five basic tastes represented by savory, salty, sour, bitter, and umami (うま味), mellow, full, long, harmonious, etc., are also enhanced by the surrounding tastes of the above basic tastes. [0003] On the other hand, calcium sensing receptor (Calcium Sensing Receptor: CaSR) is also called calcium receptor, and the receptor signal regulates various biological functions, and a substance having CaSR agonist activity can be used as a kokumi-imparting agent (Patent Document 1,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/06A23L1/226A23L1/30C07D281/06A23L27/20
CPCA23L1/22657C07K5/0215A23C9/156C07D281/06A23L27/204C07K5/06A23L27/20
Inventor 佐藤诚一二木史惠安田礼子江藤幸圣铃木裕美子田岛高穗江藤让田原优树
Owner AJINOMOTO CO INC
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