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• W2316741612 abstract "Recent work has demonstrated that 4-hydroxybenzoic acid is the in vivo precursor to the 1-(4-aminophenyl)-1-deoxy-D-ribitol (APDR) moiety present in the C(1) carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur, the hydroxyl group of the 4-hydroxybenzoic acid must be replaced with an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and liquid chromatography with electrospray-ionization mass spectroscopy, the first step of this transformation in Methanocaldococcus jannaschii occurs by the reaction of 4-hydroxybenzoic acid with phosphoribosyl pyrophosphate (PRPP) to form 4-(β-d-ribofuranosyl)hydroxybenzene 5'-phosphate (β-RAH-P). The β-RAH-P then condenses with l-aspartate in the presence of ATP to form 4-(β-d-ribofuranosyl)-N-succinylaminobenzene 5'-phosphate (β-RFSA-P). Elimination of fumarate from β-RFSA-P produces 4-(β-D-ribofuranosyl)aminobenzene 5'-phosphate (β-RFA-P), the known precursor to the APDR moiety of methanopterin [White, R. H. (1996) Biochemistry 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline." @default.
• W2316741612 created "2016-06-24" @default.
• W2316741612 creator A5066432564 @default.
• W2316741612 date "2011-06-15" @default.
• W2316741612 modified "2023-09-27" @default.
• W2316741612 title "The Conversion of a Phenol to an Aniline Occurs in the Biochemical Formation of the 1-(4-Aminophenyl)-1-deoxy-<scp>d</scp>-ribitol Moiety in Methanopterin" @default.
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• W2316741612 doi "https://doi.org/10.1021/bi200362w" @default.
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