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Mono‐( l )‐aspartylchlorin‐e 6 † ‡
Author(s) -
Hargus Jodie A.,
Fronczek Frank R.,
Vicente M. Graça H.,
Smith Kevin M.
Publication year - 2007
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2007.00092.x
Subject(s) - pheophorbide a , chemistry , nuclear magnetic resonance spectroscopy , pheophytin , residue (chemistry) , spectroscopy , derivative (finance) , stereochemistry , crystallography , photodynamic therapy , physics , organic chemistry , photosystem ii , biochemistry , photosynthesis , quantum mechanics , financial economics , economics
Mono‐( l )‐aspartylchlorin‐e 6 (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‐e 6 is definitively shown to be the isomer in which the aspartyl residue is attached at the 15 2 ‐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 15 2 ‐aspartyl derivative is proposed.