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Paper | Regular issue | Vol 48, No. 11, 1998, pp.2231-2243
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8286
The Structures of Mono-L-aspartyl Chlorin e6 and Its Related Compounds

Shuichi Gomi,* Toshio Nishizuka, Osamu Ushiroda, Naoki Uchida, Hirotada Takahashi, and Shinjiro Sumi

*Pharmaceutical Research Center, Meji Seika Kaisha Ltd., 760 Morooka-cho, Kohoku-ku, Yokohama 222-8567, Japan


Structures of the photosensitizer mono-L-aspartyl chlorin e6 (1) and its related compounds were examined by chemical studies and spectral means. It was clarified that L-aspartyl moiety of 1 was attached to acetic acid side chain of chlorin e6, therefore, the structure of 1 was established to be (2S,3S)-18-carboxy-20-[N-(S)-1,2-dicarboxyethyl]carbamoylmethyl-13-ethyl-3,7,12,17-tetramethyl-8-vinylchlorin-2-propanoic acid. The thermal degradation product was determined to be an 18-decarboxyl derivative of 1. In addition, 15N NMR as signment of 1 in DMSO-d6 solution was confirmed by 1H-15N HMQC and HMBC techniques. In comparison with 1H chemical shifts in D2O and DMSO-d6, in was deduced that 1 in water is not persent as a free molecule, but as a complex of two or more molecules.