title: The role of aromatic L-amino acid decarboxylase in bacillamide C biosynthesis by Bacillus atrophaeus C89.
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.
authors: State Key Laboratory of Microbial Metabolism and School of Life Sciences and Biotechnology, Shanghai Jiao Tong University, Shanghai 200240, P.R. China.
authors: Lei
authors: L
authors: Yuwen
authors: Feng-Li
authors: FL
authors: Zhang
authors: Qi-Hua
authors: QH
authors: Chen
authors: Shuang-Jun
authors: SJ
authors: Lin
authors: Yi-Lei
authors: YL
authors: Zhao
authors: Zhi-Yong
authors: ZY
authors: Li
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D001142:Aromatic-L-Amino-Acid Decarboxylases / Q000235:genetics / Q000378:metabolism*; D001407:Bacillus / Q000201:enzymology / Q000235:genetics / Q000378:metabolism*; D003653:Decarboxylation; D047088:Dysidea / Q000235:genetics / Q000378:metabolism; D008969:Molecular Sequence Data; D010453:Peptide Synthases / Q000235:genetics / Q000378:metabolism; D010649:Phenylalanine / Q000235:genetics / Q000378:metabolism; D016415:Sequence Alignment; D013844:Thiazoles / Q000378:metabolism; D014363:Tryptamines / Q000096:biosynthesis* / Q000378:metabolism; D014364:Tryptophan / Q000235:genetics / Q000378:metabolism
chemical_list: D013844:Thiazoles; D014363:Tryptamines; C525340:bacillamide C; C030820:tryptamine; D010649:Phenylalanine; D014364:Tryptophan; D001142:Aromatic-L-Amino-Acid Decarboxylases; D010453:Peptide Synthases
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