| The Conversion of a Phenol to an Aniline Occurs in the Biochemical Formation of the 1-(4-Aminophenyl)-1-deoxy-D-ribitol moiety in Methanopterin. | |
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MedLine Citation:
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PMID: 21634403 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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 C1 carrier coenzyme methanopterin present in the methanogenic archaea. For this transformation to occur the hydroxyl group of the 4-hydroxybenzoic acid must be replaced by an amino group at some point in the biosynthetic pathway. Using stable isotopically labeled precursors and LC-ESI-MS, 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-succinyl-aminobenzene 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. Biochemistry (1996) 35, 3447-3456]. This work represents the first biochemical example of the conversion of a phenol to an aniline. |
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Authors:
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Robert H White |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-6-2 |
Journal Detail:
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Title: Biochemistry Volume: - ISSN: 1520-4995 ISO Abbreviation: - Publication Date: 2011 Jun |
Date Detail:
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Created Date: 2011-6-3 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0370623 Medline TA: Biochemistry Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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