Concise Synthesis of Photocleavable Molecular Tag for Laser Desorption Ionization Mass Spectrometry via Fries Reaction

Abstract

A new synthetic route for the photocleavable molecular tag for laser desorption ionization mass spectrometry (LDI-MS) was achieved using the Fries reaction of 2,6-dimethylphenyl ester as its key reaction. Zirconium chloride was used as uniquely efficient adjuvant to promote the reaction. The molecular tag was obtained in five steps without chromatographic purification.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

GRAPHICAL ABSTRACT

Keywords:

• Fries reaction
• photocleavable molecular tag
• without chromatographic purification

ACKNOWLEDGMENT

This study was supported by a Grant-in-Aid (No. 21550160) from the Ministry of Education, Science, and Culture, Japan.

Notes

^a Determined by HPLC analysis.

^b Scaled up reaction (see text).