Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester

	Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester
	Tao, H; Cui, DF; Zhang, YS
刊名	ACTA BIOCHIMICA ET BIOPHYSICA SINICA
	2004
卷号	36 期号:6 页码:385-389
关键词	artificial sweetener aspartame derivative peptide bond
通讯作者	Zhang, YS (reprint author), Chinese Acad Sci, Shanghai Inst Biol Sci, Inst Biochem & Cell Biol, Shanghai 200031, Peoples R China.,yszhang@sibs.ac.cn
英文摘要	An aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester was synthesized with aspartic acid replaced by asparagine and peptide bond replaced by ester bond. The aspartic acid of aspartame could be replaced by asparagine as reported in the literature. In this analogue, the hydrogen of amide group could still form a hydrogen bond with the oxygen of ester bond and the ester bond was isosteric with peptide bond. However, the product was not sweet, showing that the peptide bond could not be replaced by ester bond. The peptide C-N bond behaves as a double bond that is not free to rotate and the C, 0, N and H atoms are in the same plane. The replacement of peptide bond by ester bond destroyed the unique conformation of peptide bond, resulting in the loss of sweet taste.
学科主题	Biochemistry & Molecular Biology; Biophysics
类目[WOS]	Biochemistry & Molecular Biology ; Biophysics
关键词[WOS]	TASTE ; SWEETNESS
收录类别	SCI
语种	英语
WOS记录号	WOS:000222254900002
内容类型	期刊论文
版本	出版稿
源URL	[http://202.127.25.143/handle/331003/2096]
专题	上海生化细胞研究所_上海生科院生化细胞研究所
推荐引用方式 GB/T 7714	Tao, H,Cui, DF,Zhang, YS. Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester[J]. ACTA BIOCHIMICA ET BIOPHYSICA SINICA,2004,36(6):385-389.
APA	Tao, H,Cui, DF,&Zhang, YS.(2004).Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester.ACTA BIOCHIMICA ET BIOPHYSICA SINICA,36(6),385-389.
MLA	Tao, H,et al."Synthesis and characteristics of an aspartame analogue, L-asparaginyl L-3-phenyllactic acid methyl ester".ACTA BIOCHIMICA ET BIOPHYSICA SINICA 36.6(2004):385-389.