Mono-(L)-aspartylchlorin-e₆

Jodie A. Hargus, Louisiana State University
Frank R. Fronczek, Louisiana State University
M. Gra̧a H. Vicente, Louisiana State University
Kevin M. Smith, Louisiana State University

Abstract

Mono-(l)-aspartylchlorin-e6 (also known as Talaporfin, NPe6, MACE, and most recently LS-11) is a potent sensitizer for photodynamic therapy that is currently undergoing clinical trials. Using a combination of unambiguous partial synthesis from pheophytin-a and methyl pheophorbide-a, NMR spectroscopy, and single crystal X-ray diffraction, the structure of mono-(l)-aspartylchlorin-e6 is definitively shown to be the isomer in which the aspartyl residue is attached at the 152-side chain position. This conclusion is contrary to earlier assumptions, but affirms the conclusions of a study based on NMR spectroscopy; a rationale for the unique formation of the 152-aspartyl derivative is proposed. © 2007 The Authors.