新型高倍二肽甜味剂的制备与表征

Preparation and characterization of new high-potency dipeptide sweetener

N-{N-[3-甲基-3-(3,4-亚甲二氧基苯基)丁基]-α-L-天冬氨酰}-L-苯丙氨酸甲酯是一种新型纽甜类似物甜味剂。以3,4-亚甲基苯硼酸,3,3-二甲基丙烯酸为原料,经过Heck反应、酯化反应及DIBAL-H还原得到了3-甲基-3-(3,4-亚甲二氧基苯基)丁醛中间体。然后该中间体与阿斯巴甜在钯/碳催化作用下进行氢化还原氨化反应,成功制备了目标产物N-{N-[3-甲基-3-(3,4-亚甲二氧基苯基)丁基]-α-L-天冬氨酰}-L-苯丙氨酸甲酯。产物采用了核磁共振(NMR)、红外光谱(IR)和高分辨质谱(HRMS)等技术进行结构鉴定和分析,最后确证无误。经感官评定,测得其甜度约为蔗糖的3万倍。

N-{N-[3-methyl-3-(3,4-methylenedioxyphenyl)butyl]-α-L-aspartyl}-L-phenylalanine methyl ester is a new sweetener of neotame analogues.In this paper,to synthesize this sweetener,designed the strategy to obtain the key intermediate 3-methyl-3-(3,3-methylenedioxyphenyl)butyraldehyde.Use 3,4-methylenedioxybenzenboronic acid and 3,3-dimethylacrylic acid as starting material through Heck reaction,esterification and DIBAL-H reduction to get the intermediate successfully.Then the target sweetener was synthesized by the reductive amination of 3-methyl-3-(3,4-methylenedioxyphenyl)butyraldehyde with aspartame,which was catalyzed by palladium/carbon under the hydrogen atmosphere.The structure of the final product was identified by NMR,IR and HRMS,and the results matched with the desired sweetener.After being verified by sensory evaluation,the sweetness is about 30000 times than sucrose.