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The Role of Aromatic L-amino Acid Decarboxylase in Bacillamide C Biosynthesis by Bacillus Atrophaeus C89

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Journal Sci Rep
Specialty Science
Date 2013 May 1
PMID 23628927
Citations 14
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Abstract

For biosynthesis of bacillamide C by Bacillus atrophaeus C89 associated with South China sea sponge Dysidea avara, it is hypothesized that decarboxylation from L-tryptophan to tryptamine could be performed before amidation by the downstream aromatic L-amino acid decarboxylase (AADC) to the non-ribosomal peptide synthetases (NRPS) gene cluster for biosynthesizing bacillamide C. The structural analysis of decarboxylases' known substrates in KEGG database and alignment analysis of amino acid sequence of AADC have suggested that L-tryptophan and L-phenylalanine are the potential substrates of AADC. The enzymatic kinetic experiment of the recombinant AADC proved that L-tryptophan is a more reactive substrate of AADC than L-phenylalanine. Meanwhile, the AADC-catalyzed conversion of L-tryptophan into tryptamine was confirmed by means of HPLC and LC/MS. Thus during bacillamide C biosynthesis, the decarboxylation of L-tryptophan to tryptamine is likely conducted first under AADC catalysis, followed by the amidation of tryptamine with the carboxylic product of NRPS gene cluster.

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References
1.
Pennings E, Hegger I, van der Heijden R, Duine J, Verpoorte R . Assay of tryptophan decarboxylase from Catharanthus roseus plant cell cultures by high-performance liquid chromatography. Anal Biochem. 1987; 165(1):133-6. DOI: 10.1016/0003-2697(87)90210-7. View

2.
Bradford M . A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976; 72:248-54. DOI: 10.1016/0003-2697(76)90527-3. View

3.
Wang W, Joyner S, Khoury K, Domling A . (-)-Bacillamide C: the convergent approach. Org Biomol Chem. 2010; 8(3):529-32. DOI: 10.1039/b918214d. View

4.
Healy F, Wach M, Krasnoff S, Gibson D, Loria R . The txtAB genes of the plant pathogen Streptomyces acidiscabies encode a peptide synthetase required for phytotoxin thaxtomin A production and pathogenicity. Mol Microbiol. 2000; 38(4):794-804. DOI: 10.1046/j.1365-2958.2000.02170.x. View

5.
Vollbrecht L, Steinmetz H, Hofle G, Oberer L, Rihs G, Bovermann G . Argyrins, immunosuppressive cyclic peptides from myxobacteria. II. Structure elucidation and stereochemistry. J Antibiot (Tokyo). 2002; 55(8):715-21. DOI: 10.7164/antibiotics.55.715. View