JPH0530839B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention is directed to L-aspartyl-D-alanine-(-),α, which is a novel compound that has excellent sweetness properties and can be widely used as a sweetener in foods, drinks, medicines, etc.
- Concerning phenthyl ester. [Prior art] Currently, sucrose is the most widely used sweetener, but due to increasing awareness of preventing tooth decay, obesity due to excessive calorie intake, diabetes, heart disease, high blood pressure, kidney disease, etc., sucrose is being replaced. There is a strong demand for anti-cariogenic, low-calorie sweeteners, and we are already focusing on natural sweeteners such as glycyrrhizin, stevioside, thaumatin, and L-aspartyl/L-phenylalanine methyl ester (hereinafter abbreviated as APM). Many artificial sweeteners have been developed, some of which have been commercialized. However, natural sweeteners have drawbacks in the quality of sweetness and aftertaste, and are expensive, so none of them are satisfactory. In addition, due to toxicity, the mainstream of artificial sweeteners is currently dipeptide-based sweeteners, mainly APM, but most of them have a sweetness level of 150 to 200 times that of APM, which is less than 500 times that of sucrose. It was not sufficient, and also tended to undergo hydrolysis reactions and diketopiperazine formation reactions in aqueous solutions, resulting in stability problems. As a dipeptide sweetener with enhanced sweetness, L-aspartyl/DL-methyl aminomalonate/fuentyl diester (hereinafter referred to as
(abbreviated as AMF), and its sweetness is comparable to that of sucrose.
It is said to be more than 20,000 times. However, since this substance contains aminomalonic acid in its molecule, it is easily decomposed in an aqueous solution.For example, its stability at 80℃PH4 is
It has disadvantages that are inferior to APM (see Figure 1). In addition, as examples of dipeptide sweeteners with improved stability, there are many branched-chain amides of L-aspartyl-D-amino acid dipeptides disclosed in JP-A No. 56-127339, but these sweeteners have a sweetness level even at the highest level. It is about 600 times more than sucrose, which is not completely satisfactory. As described above, no satisfactory sweetener has yet been found to replace sucrose, neither natural sweeteners nor artificial sweeteners. [Problems to be Solved by the Invention] Therefore, an object of the present invention is to provide a dipeptide sweetener that has a sweetness quality similar to that of sucrose, has a high degree of sweetness, is low in calories, and is stable in an aqueous solution. There is a particular thing. [Means for Solving the Problems] As a result of extensive research in order to obtain a dipeptide sweetener that solves these problems, the present inventors have developed a new compound, aspartyl-alanine-
We discovered that fenthyl ester is superior to APM in terms of sweetness, stability, and solubility in water, and filed a patent application earlier (patent application filed in 1983).
No. 42440). The present inventors further studied the three-dimensional structure of this aspartyl-alanine-phentyl ester, and found that L-aspartyl-D-alanine-(-), α-phentyl ester has a sweetness similar to that of sucrose. The present invention was completed based on the discovery that it is an almost ideal sweetener that has 1200 times the sweetness of sucrose, is low in calories, and is extremely stable in an aqueous solution. That is, the present invention is based on the formula () L, a novel dipeptide sweetener represented by
-Aspartyl-D-alanine-(-), α-phentyl ester (hereinafter abbreviated as AFα). The compound AFα of the present invention is synthesized, for example, by the method shown by the following reaction formula. Z = carbobenzoxy group Bzl = benzyl group Fen = (-), α-phentyl group In other words, amino group is replaced with carbobenzoxy group, β
-L with carboxyl group protected with benzyl group etc.
The target product AFα can be obtained by condensing aspartic acid and separately prepared α-phentyl-D-alanine in the presence of a base, and then removing the protecting group by catalytic reduction or the like. can. The AFα thus obtained is a colorless and odorless powder that dissolves in water more easily than APM. The diluted aqueous solution has excellent sweetness similar to sucrose, and has almost no unpleasant taste such as bitterness, sarcasm, or bad aftertaste that is found in many artificial sweeteners, and its sweetness is 1200 times higher than that of sucrose. It is 8 times the APM and shows a satisfactory height. Thermal stability and stability in aqueous solutions are far superior to APM, as shown in Figures 1 and 2. Furthermore, since AFα contains D-type amino acids in its molecule, there is little concern that many dipeptide sweeteners made of L-type amino acids lack stability against oxygen. Due to these excellent sweetness properties, AFα of the present invention can be used alone or as a sweetener with glucose,
It can be widely used in foods, drinks, and medicines as a powder with dextrin, a solution with water, alcohol, propylene glycol, etc., or an emulsion mixed with an emulsifier. For example, fruit juice, soft drinks, lactic acid drinks, carbonated drinks, and their powdered drinks, alcoholic beverages such as sake, synthetic alcohol, and fruit alcohol, miso,
Seasonings such as soy sauce, sauce, vinegar, mirin, dressing, mayonnaise, ketchup, frozen desserts such as ice cream and sherbett, confectionery such as canday, chocolate, jelly, biscuits, Japanese sweets, Western sweets, chewing gum, jam, marmalade items, snack foods, bacon,
It can be used in meat products such as ham and sausages, fish paste products such as kamaboko and chikuwa, tsukudani and canned foods, as well as oral medicines, toothpaste, and gargles. The amount added is not particularly limited and may be appropriately selected depending on the object and purpose of use. [Example] Next, the present invention will be explained in more detail by giving comparative examples, examples, and usage examples. Comparative Example 1 AFα, APM, and sucrose were dissolved and diluted in water, and their threshold values were determined by the limit method using a panel of five experienced flavorists. The results are shown in Table 1.

〔Effect of the invention〕

The present invention provides a novel L-aspartyl-D-alanine-(-), α-phentyl ester, which has a sweetness quality similar to that of sucrose, a high degree of sweetness, and is stable in an aqueous solution. It can be used as a sweetener in a wide range of fields without any restrictions.

[Brief explanation of the drawing]

Figures 1 and 2 are diagrams showing the stability of the compound AFα of the present invention in an aqueous solution, and Figure 3 is a diagram showing the stability of the compound AFα of the present invention in an aqueous solution.
The NMR spectrum of AFα is shown in Figure 4, and the MS of AFα is shown in Figure 4.
The spectrum is shown.

Claims (1)

[Claims] Linear formula () L-aspartyl-D-alanine-
(-), α-phenthyl ester