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Issue 1, 2012
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Aminobenzoates as building blocks for natural productassembly lines

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Abstract

Covering: up to the end of September 2011

The ortho-, meta-, and para- regioisomers of aminobenzoate are building blocks for a wide range of microbial natural products. Both the ortho-isomer (anthranilate) and PABA derive from the central shikimate pathway metabolite chorismate while the meta-isomer is not available by that route and starts from UDP-3-aminoglucose. PABA is largely funnelled into folate biosynthesis while anthranilate is the scaffold for biosynthetic elaboration into many natural heterocycles, most notably with its role in indole formation for tryptophan biosynthesis. Anthranilate is also converted to benzodiazepinones, fumiquinazolines, quinoxalines, phenoxazines, benzoxazolinates, quinolones, and phenazines, often with redox enzyme participation. The 5-hydroxy form of 3-aminobenzaote is the starter unit for ansa-bridged rifamycins, ansamitocins, and geldanamycins, whereas regioisomers 2-hydroxy, 4-hydroxy and 2,4-dihydroxy-3-aminobenzoate are key components of antimycin, grixazone, and platencin and platensimycin biosynthesis, respectively. The enzymatic mechanisms for generation of the aminobenzoate regioisomers and their subsequent utilization for diverse heterocycle and macrocycle construction are examined.

Graphical abstract: Aminobenzoates as building blocks for natural product assembly lines

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Publication details

The article was received on 23 Sep 2011 and first published on 08 Nov 2011


Article type: Review Article
DOI: 10.1039/C1NP00072A
Nat. Prod. Rep., 2012,29, 37-59

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    Aminobenzoates as building blocks for natural product assembly lines

    C. T. Walsh, S. W. Haynes and B. D. Ames, Nat. Prod. Rep., 2012, 29, 37
    DOI: 10.1039/C1NP00072A

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