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  • Title: Pheophytinization kinetics of chlorophyll c under weakly acidic conditions: effects of acrylic acid residue at the 17-position.
    Author: Sadaoka K, Shoji S, Hirota K, Tsukatani Y, Yoshitomi T, Tamiaki H, Kashimura S, Saga Y.
    Journal: Bioorg Med Chem; 2013 Nov 15; 21(22):6915-9. PubMed ID: 24095012.
    Abstract:
    Pheophytinization of chlorophyll (Chl) c1, which was isolated from the diatom Chaetoceros gracilis, was kinetically analyzed under weakly acidic conditions, and was compared with that of protochlorophyllide (PChlide) a and chlorophyllide (Chlide) a. Chl c1 possessing a trans-acrylic acid residue at the 17-position exhibited slower pheophytinization kinetics than PChlide a and Chlide a, both of which possessed a propionic acid residue at the same position. The difference in pheophytinization properties between Chl c1 and (P)Chlide a was ascribable to the electronegativity of the 17-substituent in Chl c1 larger than that of (P)Chlide a due to the C17(1)-C17(2) double bond with the conjugated 17(2)-carboxy group in Chl c1. Demetalation kinetics of PChlide a was slower than that of Chlide a, which originated from the effect of the π-macrocyclic structures.
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