12624-18-9

Basic information

• Product Name: (S)-4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid
• Synonyms: (S)-4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid;Muscaflavin
• CAS NO: 12624-18-9
• Molecular Formula: C9H9 N O5
• Molecular Weight: 211.17
• Mol File: 12624-18-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid(12624-18-9)
• EPA Substance Registry System: (S)-4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid(12624-18-9)

Safety Data

• Hazardous Substances Data: 12624-18-9(Hazardous Substances Data)

Usage

General Description

(S)-4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid, also known as FAD, is a chemical compound with a molecular formula of C9H7NO5. It is a component of the flavin adenine dinucleotide (FAD), which is a redox cofactor involved in various biological processes, including energy production and metabolism. FAD plays a crucial role in the electron transport chain and is essential for the synthesis of ATP in cells. (S)-4-Formyl-2,3-dihydro-1H-azepine-2,7-dicarboxylic acid is also involved in various enzymatic reactions, serving as a coenzyme for several enzymes, such as dehydrogenases and oxidases. FAD is found in all living organisms and is vital for numerous cellular processes, making it a key molecule in biochemistry and physiology.

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Relevant articles and documents

The formation of betalamic acid and muscaflavin by recombinant DOPA- dioxygenase from Amanita

DOPA-dioxygenase from Amanita muscaria is known to catalyse the conversion of 3-(3,4-dihydroxyphenyl)alanine (DOPA) to betalamic acid in the key reaction of betalain biosynthesis. In this work, we re-examined the reactivity of DOPA-dioxygenase using a cDNA clone encoding active DOPA- dioxygenase the kinetic parameters of which were comparable to those of the native enzyme. Using L-DOPA as a substrate, the enzyme catalysed the formation of two products. In addition to betalamic acid, the enzyme also catalysed the formation of muscaflavin, a compound that occurs naturally in A. muscaria and in mushrooms of the Hygrocybe family but not in the betalain- containing plants of the order Caryophyllales. Muscaflavin arises by a 2,3- extradiol cleavage of DOPA, whereas betalamic acid is the product of a 4,5- cleavage. Our results indicate that the recombinant enzyme has both 2,3- and 4,5-dioxygenase activity, and do not support the prevailing view that the two compounds are produced by two distinct enzymes.

Colouring Matters from Fly Agaric, VII. - Constitution and Synthesis of Muscaflavin

The constitution of the yellow dihydroazepine amino acid muscaflavin, isolated from mushrooms, has been established as 1a.This was confirmed by a biomimetic synthesis of the DL ester 1b, starting from pyridylalanine 12a via the glutaconic dialdehyde inter