TY - JOUR
T1 - Biosynthesis of amphi-enterobactin siderophores by Vibrio harveyi BAA-1116
T2 - Identification of a bifunctional nonribosomal peptide synthetase condensation domain
AU - Zane, Hannah K.
AU - Naka, Hiroaki
AU - Rosconi, Federico
AU - Sandy, Moriah
AU - Haygood, Margo G.
AU - Butler, Alison
PY - 2014/4/16
Y1 - 2014/4/16
N2 - The genome of Vibrio harveyi BAA-1116 contains a nonribosomal peptide synthetase (NRPS) gene cluster (aebA-F) resembling that for enterobactin, yet enterobactin is not produced. A gene predicted to encode a long-chain fatty acid CoA ligase (FACL), similar to enzymes involved in the biosynthesis of acyl peptides, resides 15 kb away from the putative enterobactin-like biosynthetic gene cluster (aebG). The proximity of this FACL gene to the enterobactin-like synthetase suggested that V. harveyi may produce amphiphilic enterobactin-like siderophores. Extraction of the bacterial cell pellet of V. harveyi led to the isolation and structure determination of a suite of eight amphi-enterobactin siderophores composed of the cyclic lactone of tris-2,3-dihydroxybenzoyl-l- serine and acyl-l-serine. The FACL knockout mutant, "aebG V. harveyi, and the NRPS knockout mutant, "aebF V. harveyi, do not produce amphi-enterobactins. The amphi-enterobactin biosynthetic machinery was heterologously expressed in Escherichia coli and reconstituted in vitro, demonstrating the condensation domain of AebF has unique activity, catalyzing two distinct condensation reactions.
AB - The genome of Vibrio harveyi BAA-1116 contains a nonribosomal peptide synthetase (NRPS) gene cluster (aebA-F) resembling that for enterobactin, yet enterobactin is not produced. A gene predicted to encode a long-chain fatty acid CoA ligase (FACL), similar to enzymes involved in the biosynthesis of acyl peptides, resides 15 kb away from the putative enterobactin-like biosynthetic gene cluster (aebG). The proximity of this FACL gene to the enterobactin-like synthetase suggested that V. harveyi may produce amphiphilic enterobactin-like siderophores. Extraction of the bacterial cell pellet of V. harveyi led to the isolation and structure determination of a suite of eight amphi-enterobactin siderophores composed of the cyclic lactone of tris-2,3-dihydroxybenzoyl-l- serine and acyl-l-serine. The FACL knockout mutant, "aebG V. harveyi, and the NRPS knockout mutant, "aebF V. harveyi, do not produce amphi-enterobactins. The amphi-enterobactin biosynthetic machinery was heterologously expressed in Escherichia coli and reconstituted in vitro, demonstrating the condensation domain of AebF has unique activity, catalyzing two distinct condensation reactions.
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U2 - 10.1021/ja5019942
DO - 10.1021/ja5019942
M3 - Article
C2 - 24701966
AN - SCOPUS:84898982654
SN - 0002-7863
VL - 136
SP - 5615
EP - 5618
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 15
ER -