Synthesis of Methoxy-Substituted Diazirinyl Phenylalanine – A Novel Photoreactive Aspartame Derivative for Functional Analysis of Sweet Receptors

摘要

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. Trifluoromethyl- diazirine, 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.