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Citation: Zeng Guangzhi. STRUCTURE-ACTIVITY RELATIONSHIPS OF DI-AND TRIPEPTIDE SWEETENERS[J]. Chinese Journal of Applied Chemistry, ;1990, 7(1): 1-9. shu

STRUCTURE-ACTIVITY RELATIONSHIPS OF DI-AND TRIPEPTIDE SWEETENERS

Zeng Guangzhi

1.
Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai 200032

Received Date: 7 April 1989
Available Online: 24 June 1989

A U-shaped induced-fitting model of sweet-bitter receptor with multiple point attach-ment was proposed by the author in 1980. In this paper it is employed to illustrate the structure-activity relationships of di- and tripeptide sweeteners analogous to Aspartame.The glucophore is taken to be G=^-O₂C(CH₂)_0-1 CHNH₂⁺R when R=H, the auxogluc on the N-end to be A^N=R when R=any acyl group and that on the C-end to be A^c=CONH-CR¹R²R³ where R³ > R² > R¹ in size. The main chains of both A^N and A^c will attain a maximal sweetness, if either or both can reach the C-9 position of the top layer of the receptor membrane. However, the depth where the main chain of A^N or A^c can reach de-pends on the orientation and position where G is ancholed on the sulface. Nevertheless, itwill cause the highest perturbation shuold it reach this C-9 position. Thus the optimal chainlength of an auxogluc is often equivalent to no more or less than that of a C₈ to C₁₀ acyl group. If one supposes that the size instead of the atomic number of substituents R¹ > R² > R³ on the dissymmetric α-carbon atom be adopted as the standard for what we call "topo" configuration, then the three amino acids in paralle connection A^N-G-A^c must allbe of a "topo"-D-configuration to have a high sweetness intensity whiie only an A₂^c of them in series connection G-A₁^c-A₂^c must be of a "topo"-L enantiomer. For a dipeptide G-A^c, the width R¹-C-R² of A^c must be≤(CH₂)₄;for a tripeptide G-A₁^c-A₂^c, that of A₂^c must be≤(CH₂)₅. The polar, steric and hydrophobic effects of substituents on R, R² and R³ have understandable influences, inter alia, on the stability as well as sweetness intensity of these concerned sweetencrs.
- glucophore,
- auxogluc,
- C-9 rule,
- "topo"configuration
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