16883-97-9

Basic information

• Product Name: 3-[2-[(Z)-[(5E)-3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-pyrrol-2-yl)methylene]-4-methyl-pyrrol-2-ylidene]methyl]-5-[(Z)-[(3E,4R)-3-ethylidene-4-methyl-5-oxo-pyrrolidin-2-ylidene]methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid
• CAS NO: 16883-97-9
• Molecular Formula: C₃₃H₃₈N₄O₆
• Molecular Weight: 586.678
• Mol File: 16883-97-9.mol
• Article Data: 9

Chemical Properties

• Refractive Index: 1.639
• CAS DataBase Reference: 3-[2-[(Z)-[(5E)-3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-pyrrol-2-yl)methylene]-4-methyl-pyrrol-2-ylidene]methyl]-5-[(Z)-[(3E,4R)-3-ethylidene-4-methyl-5-oxo-pyrrolidin-2-ylidene]methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-[(Z)-[(5E)-3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-pyrrol-2-yl)methylene]-4-methyl-pyrrol-2-ylidene]methyl]-5-[(Z)-[(3E,4R)-3-ethylidene-4-methyl-5-oxo-pyrrolidin-2-ylidene]methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid(16883-97-9)
• EPA Substance Registry System: 3-[2-[(Z)-[(5E)-3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-pyrrol-2-yl)methylene]-4-methyl-pyrrol-2-ylidene]methyl]-5-[(Z)-[(3E,4R)-3-ethylidene-4-methyl-5-oxo-pyrrolidin-2-ylidene]methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid(16883-97-9)

Safety Data

• Hazardous Substances Data: 16883-97-9(Hazardous Substances Data)

Upstream product

• 635-65-4 bilirubin IXα 
• 902268-70-6 biliverdin IXα 
• 220182-72-9 N-(t-butyloxycarbonyl)-4-(1-methoxyethyl)-3-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one 
• 220182-68-3 4-(1-bromoethyl)-1-t-butoxycarbonyl-1,5-dihydro-3-methyl-5-tosyl-2H-pyrrol-2-one 
• 220182-64-9 1-t-butoxycarbonyl-4-ethyl-1,5-dihydro-3-methyl-5-tosyl-2H-pyrrol-2-one 
• 220182-46-7 4-(1-methoxyethyl)-3-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one 
• 215871-79-7 3-Eth-(E)-ylidene-1-(4-methoxy-benzyl)-pyrrolidine-2,5-dione 
• 215871-89-9 1-(4-Methoxy-benzyl)-3-methyl-pyrrole-2,5-dione 
• 215871-90-2 3-Eth-(E)-ylidene-1-(4-methoxy-benzyl)-4-methyl-pyrrolidine-2,5-dione 
• 152796-98-0 4-ethyl-3-methyl-5-(p-toluenesulfonyl)-1,5-dihydro-1H-pyrrolin-2-one 
• 42419-19-2 tert-butyl 3-(2-methoxycarbonylethyl)-4-methylpyrrole-2-carboxylate 
• 616-02-4 citraconic acid anhydride 
• 263898-88-0 3-(2-Allyloxycarbonyl-ethyl)-4-methyl-5-{4-methyl-5-oxo-3-[1-(toluene-4-sulfonyl)-ethyl]-4,5-dihydro-1H-pyrrol-2-ylmethyl}-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 263898-72-2 5-acetoxy-5-(t-butoxycarbonyl)-3-ethyl-1,5-dihydro-4-methyl-2H-pyrrol-2-one 

Downstream Products

• 493-88-9 mesobiliverdin IXα 

Relevant articles and documents

Biliverdin amides reveal roles for propionate side chains in bilin reductase recognition and in holophytochrome assembly and photoconversion

Linear tetrapyrroles (bilins) perform important antioxidant and light-harvesting functions in cells from bacteria to humans. To explore the role of the propionate moieties in bilin metabolism, we report the semisynthesis of mono- and diamides of biliverdin IXα and those of its non-natural XIIIα isomer. Initially, these were examined as substrates of two types of NADPH-dependent biliverdin reductase, BVR and BvdR, and of the representative ferredoxin-dependent bilin reductase, phycocyanobilin:ferredoxin oxidoreductase (PcyA). Our studies indicate that the NADPH-dependent biliverdin reductases are less accommodating to amidation of the propionic acid side chains of biliverdin IXα than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides were also assembled with BV-type and phytobilin-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native Pr dark states of these biliprotein photosensors. Neither ionizable propionate side chain proved to be essential to primary photoisomerization for both classes of phytochromes, but an unsubstituted 12-propionate was required for full photointerconversion of phytobilin-type phytochrome Cph1. Taken together, these studies provide insight into the roles of the ionizable propionate side chains in substrate discrimination by two bilin reductase families while further underscoring the mechanistic differences between the photoconversions of BV-type and phytobilin-type phytochromes.

An efficient method for the conversion of 2-bromo-5-tosylpyrroles to the corresponding 5-tosylpyrrolinones as the D-ring of phycocyanobilin derivatives

2-Bromo-5-tosylpyrroles were efficiently converted to the corresponding 5-tosylpyrrolinones as the D-ring of phycocyanobilin (PCB) derivatives by treating with DMSO and Zn in TFA in the presence of a catalytic amount of iodine. PCB derivatives modified at the D-ring were prepared in free acid forms employing the resulting 5-tosylpyrrolinones toward structure/function analysis of phytochrome.

An efficient method to construct the A,B-rings component toward total syntheses of phycocyanobilin and its derivative as a photoprobe

Total syntheses of physocyanobilin and its derivative bearing a photoreactive group at the D-ring accomplished by developing a new and efficient method for the construction of A,B-rings component, which consists of the Wittig-type new coupling reaction of 4-(1-methoxyethyl or 1- tosylethyl)-3-methyl-5-tosyl-1,5-dihydro-2H-pyrrol-2-one and a 2-formyl pyrrole derivative in the presence of (n)Bu3P and a base, followed by reduction with aluminum amalgam and a subsequent acid or base treatment.