Ajinomoto Co., Ltd.

Ryoichiro Nakamura

Tadashi Takemoto

Yusuke Amino

Kazuko Yuzawa

Toyoto Hijiya

Naoko Sugiyama

Yusuki Amino

The present invention provides N-alkylaspartyl dipeptideester compounds and salts thereof, such as N-[N-[3-(3-hydroxy-4-methoxyphenyl)-3-methylbutyl]-L-&#x3b1;-aspartyl]-L-phenylalanine 1-methyl ester, which provide high degrees of sweetness in comparison to conventional products, compositions and products containing the novel aspartyl dipeptide ester compounds and method of producing the novel aspartyl dipeptide ester compounds.

N-alkylaspartyl dipeptide ester compounds

Aspartyl dipeptide ester derivatives, such as a N-&lsqb;N-&lsqb;3-(3,4-dihydroxyphenyl)-3-methylbutyl&rsqb;-L-&agr;-aspartyl&rsqb;-L-phenylalanine 1-methyl ester, or salts thereof, having a high degree of sweetness compared to conventional sweeteners. These derivatives are excellent in sweetening potency and may be used as sweetener components in products such as foods and drinks. They may also be used as low calorie sweeteners and in methods of sweetening products. Foods and drinks comprising these derivatives as well as methods for their production.

Aspartyl dipeptide ester derivatives and sweeteners

The present invention relates to novel, aspartyl dipeptide ester derivatives and salts thereof, such as N-&lsqb;N-(3-(3-hydroxy-4-methoxyphenyl)propyl&rsqb;-L-&agr;-aspartyl&rsqb;-L-(&agr;-methyl)phenylalanine 1-methyl ester which provide high degrees of sweetness in comparison to conventional products, compositions and products containing the novel aspartyl dipeptide ester derivatives and method of producing the novel aspartyl dipeptide ester derivatives.

Low-calory sweeteners comprising novel aspartyl dipeptide ester derivatives and their salts have a sweetening potency of up to 35000 times that of sugar and include compounds such as N-&lsqb;N-&lsqb;3-(3-methyl-4-hydroxyphenyl)propyl&rsqb;-L-&agr;-aspartyl&rsqb;-L-phenylalanine 1-methyl ester and N-&lsqb;N-&lsqb;3-(3-hydroxy-4-methoxyphenyl)propyl&rsqb;-L-&agr;-aspartyl&rsqb;-L-phenylalanine 1-methyl ester.

Novel aspartylamide derivatives such as N-(.alpha.-L-aspartyl-(1R,2S,4S)-1-methyl-2-hydroxy-4-phenylhexylamide, N-.alpha.-7(N'-3,3-dimethylbutylaspartyl)-(1R,2S,4S)-1-methyl-2-hydroxy-4- phenylhexylamide) and the like, and a sweetener containing the above-mentioned derivatives or salts thereof as an active ingredient, is low-calory and which exhibits a high level of stability, an excellent safety and an excellent sweetness.

Aspartylamide derivatives and sweeteners

Novel dipeptide derivatives, such as N-3,3-dimethylbutyl-.alpha.-L-aspartyl-.alpha.-methyl-L-phenylalanine methyl ester and N-3,3-dimethylbutyl-.alpha.-L-aspartyl-.alpha.-methyl-L-tyrosine methyl ester, and sweetening agents comprising, as the active ingredient, anyone of the derivatives and their salts, being low-calorie sweetening agents which are excellent in stability, safety and degree of sweetness, are provided. The products to have been sweetened, comprising such above sweetening agents are also provided.

Dipeptide derivatives and sweetening agents

Novel aspartyldipeptidoamides and salts thereof. The apartyldipeptides are useful as a low-calorie sweetener for food and beverage products and have excellent taste and chemical stability.

Aspartyl dipeptide amide derivatives and sweeteners

Novel aspartyldipeptideamide derivatives of formula (I):

Aspartyldipeptideamine derivatives and sweetner

Aspartyldipeptide compounds of the formula (I)

Aspartyldipeptide derivatives and sweetener compositions containing the

An economical process for producing .alpha.-L-aspartyldipeptide amide derivatives useful as sweeteners, by using amino protecting groups which can be removed by hydrolysis under acidic conditions, resulting in conversion of a .beta.-carboxyl acid ester to a carboxylic acid.

Process for producing .alpha.-l-aspartyldipeptide amide derivatives

A method of preparing .alpha.-APM derivatives without using an expensive L-phenylalanine is provided, wherein 2,5-dioxopiperazine-3-acetamide is reacted with acetic anhydride to give N,N'-diacetyl-6-cyanomethyl-2,5-dioxopiperazine, which is then reacted with benzaldehyde in the presence of a strong base to give 1-acetyl-3-benzylidene-6-cyanomethyl-2,5-dioxopiperazine. This is treated with hydrazine to give 3-benzylidene-6-cyanomethyl-2,5-dioxopiperazine, which is then reduced to prepare 3-benzyl-6-cyanomethyl-2,5-dioxopiperazine, which is converted by reaction with methanol in the presence of a strong acid to an .alpha.-APM derivative for use as a sweetener.

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Kawasaki, Japan

Ryoichiro Nakamura