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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.629-637
Published online, 12th June, 2013
DOI: 10.3987/COM-13-S(S)14
Synthesis of Methoxy-Substituted Diazirinyl Phenylalanine – A Novel Photoreactive Aspartame Derivative for Functional Analysis of Sweet Receptors

Munenori Sakurai, Katsuyoshi Masuda, Lei Wang, Yuta Murai, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, and Makoto Hashimoto*

*Division of Applied Science, Graduate School of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo, Hokkaido 060-8589, Japan

Abstract

Photoreactive phenylalanine derivatives are well known as functional analysis reagents for target biomolecules. The photophores are commonly introduced at 4-position on benzene. Aspartame, which consists of dipeptide L-Asp-L-Phe-OMe, is one of the most utilized artificial sweeteners, and substitution effects on its benzene ring have been reported. Substitution at the 4-position, however, does not maintain its sweetness properties. Trifluoromethyldiazirine, which is one of the most reliable photophores, was introduced to a different site on phenylalanine and the new photoreactive phenylalanine was converted to aspartame derivatives. The new aspartame derivative had slightly higher sweetness potency than sucrose standard solution.