title: Chlorin e6131:152-Anhydride: A Key Intermediate in Conjugation Reactions of Chlorin e6.
abstract: Since the patent for the photodynamic therapy agent Talaporfin (mono-L-aspartylchlorin e6) was issued in 1987, confusion has existed regarding which of the three carboxylic acid groups in the chlorophyll degradation product, chlorin e6(1), is modified in standard amino acid type conjugations (using DCC or EDC and an organic base) with amino acids and other biomolecules. Here it is shown that the site of conjugation is the central 152-carboxylic acid, such reactions proceeding in numerous examples via a 131,152-anhydride for which a high resolution X-ray structure is reported. Conjugation with eight oxygen and nitrogen nucleophiles, in every case, afforded the 152-conjugate, reinforcing the earlier conclusion that Talaporfin is the 152-aspartyl conjugate of chlorin e6and suggesting that reports of 173-conjugation of chlorin e6using stoichiometric peptide coupling procedures should be subjected to further scrutiny.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: Hui
authors.initials: H
authors.lastname: Chen
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: R G
authors.initials: RG
authors.lastname: Waruna Jinadasa
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: Lijuan
authors.initials: L
authors.lastname: Jiao
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: Frank R
authors.initials: FR
authors.lastname: Fronczek
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: Alex L
authors.initials: AL
authors.lastname: Nguyen
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Smith
keywords: LS-11; Talaporfin; amino acid conjugation; anhydride; chlorin e6