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• Food Chemistry •     Next Articles

Synthesis and Characteristic of a Novel Dipeptide Sweetener

nan Hu 2, 2, 2, 2,Qi-Kun TAN2,   

  • Received:2018-10-08 Revised:2019-07-29 Online:2019-09-25 Published:2019-09-23

Abstract: N-[N-[3-(3-hydroxy-4-methoxyphenyl) propyl]-L-α-aspartyl]-S-tert-butyl-L-cysteine 1-methyl ester, a novel dipeptide sweetener, is approximately 40,000 times sweeter than sucrose. 3-(3-hydroxy-4-methoxyphenyl) propanal was synthesized with isovanillin through Wittig reaction, Catalytic hydrogenation in normal temperature and pressure then reduced with Diisobutylaluminium hydride (DIBAL-H). The dipeptide was synthesized with S-tert-butyl-L-cysteine 1-methyl ester and N-(tert-butoxycarbonyl)-L-aspartic acid-4-tert-butyl ester coupled with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and 1-hydroxybenzotriazole (HOBt). N-(L-α-aspartyl)-S-tert-butyl-L-cysteine 1-methyl ester was obtained by dissolved it in the hydrochloric acid-dioxane (HCI-dioxane). Finally, the target compound with high-intensity N-[N-[3-(3-hydroxy-4-methoxyphenyl) propyl]-L-α-aspartyl]-S-tert-butyl-L-cysteine 1-methyl ester was synthesized with intermediate 3-(3-hydroxy-4-methoxyphenyl) propanal and N-(L-α-aspartyl)-S-tert-butyl-L-cysteine 1-methyl ester by catalytic hydrogenation in normal temperature and pressure. The structure of the product was identified by infrared spectroscopy, mass spectrometry and nuclear magnetic resonance to determine the structure of the target product.

Key words: High intensity Sweetness, 3-(3-hydroxy-4-methoxypenyl) propionaldehyde, dipeptide

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