34278-95-0

Basic information

• Product Name: MESOPHEOPHORBIDE A METHYL ESTER
• Synonyms: MESOPHEOPHORBIDE A METHYL ESTER
• CAS NO: 34278-95-0
• Molecular Formula: C36H40N4O5
• Molecular Weight: 608.74
• Mol File: 34278-95-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: MESOPHEOPHORBIDE A METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: MESOPHEOPHORBIDE A METHYL ESTER(34278-95-0)
• EPA Substance Registry System: MESOPHEOPHORBIDE A METHYL ESTER(34278-95-0)

Safety Data

• Hazardous Substances Data: 34278-95-0(Hazardous Substances Data)

Upstream product

• 5594-30-9 methylpheophorbide a 
• 5594-30-9 pheophorbide a methyl ester 
• 5594-30-9 pheophorbide a methyl ester 
• 186581-53-3 diazomethane 
• 15664-29-6 pheophorbide-a 

Relevant articles and documents

Detection of 132-carboxy-chlorin produced by the in vitro BciC enzymatic hydrolysis of zinc chlorophyllide

Green photosynthetic bacteria with an efficient light-harvesting system contain special chlorophyll molecules, called bacteriochlorophylls c, d, e, in their main antennae. In the biosynthetic pathway, a BciC enzyme is proposed to catalyze the hydrolysis of the C132-methoxycarbonyl group of chlorophyllide a, but the resulting C132-carboxy group has not been detected yet because it is spontaneously removed due to the instability of the β-keto-carboxylic acid. In this study, the in vitro BciC enzymatic reactions of zinc methyl (131R/S)-hydroxy-mesochlorophyllides a were examined and a carboxylic acid possessing the C132S-OH was first observed as the hydrolyzed product of the C132-COOCH3.

Physicochemical and biochemical properties of synthetic zinc 131-(un)substituted chlorophyll-a derivatives

Zinc methyl pheophorbides a/a’, which possess oxo and methoxycarbonyl groups at the C131- and C132-positions, respectively, on the exo-five membered ring fusing the cyclic tetrapyrrole of their chlorin π-skeletons, were prepared via chemical modifications of chlorophyll a produced in phototrophs. The C131-hydroxylated and unsubstituted analogues were synthesized by reduction of the ketone moiety. The C131- and C132-stereochemistry of these semi-synthetic compounds was confirmed by 1H NMR and circular dichroism spectroscopies. A methoxycarbonyl group at the chiral C132-position in the ketone was stereo-inverted under basic conditions, whereas those in the corresponding alcoholic and dihydro-forms were not. The in vitro BciC enzymatic reaction of the (132R)-ketone was found to stereoselectively hydrolyze the C132-methoxycarbonyl group, followed by spontaneous decarboxylation. Similarly, the (132R)-COOCH3 group in the (131S)-alcohol was hydrolyzed, whereas the (132R)-COOCH3 group in the (131R)-alcohol was not. After the enzymatic reaction of the C131-dihydro-compound, its (132S)-demethoxycarbonylated and hydroxylated product was observed.