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. 2011 Aug 16;12(12):1849-53.
doi: 10.1002/cbic.201100215. Epub 2011 Jun 28.

Discovery of a metagenome-derived enzyme that produces branched-chain acyl-(acyl-carrier-protein)s from branched-chain α-keto acids

Jeffrey W Craig  1 , Sean F Brady
Affiliations

Discovery of a metagenome-derived enzyme that produces branched-chain acyl-(acyl-carrier-protein)s from branched-chain α-keto acids

Jeffrey W Craig et al. Chembiochem. .
No abstract available

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Figures

Figure 1
Figure 1
A) Incorporation of FAS II intermediates (acyl-ACPs) into secondary metabolites and cofactors: N-dodecanoyl-phenylalanine (1), N-octanoyl homoserine lactone (2), enzyme-bound lipoic acid (3), and calcium-dependent antibiotic (CDA) (4). B) The domain architecture of nasB includes all three Pfam homology domains found in the E1α/E1β subuntis of 2-oxo acid dehydrogenase complexes, as well as both of the Pfam homology domains found in the E. coli FabH protein (β-ketoacyl-ACP synthase III). Separating these two sets of domains is an E2-like (E2*) lipoyl-attachment site.
Figure 2
Figure 2
API-positive mode ionization data from the HPLC-MS analysis of extracts of B. graminis cultures transformed with A) pJWC1-nasA and B) pJWC1-nasAB. Comparison of the fatty acid region of the 1D 1H NMR spectrum of C) N-dodecanoyl-phenylalanine (1) with that of D) N-(11-methyldodecanoyl)-phenylalanine (6).
Figure 3
Figure 3
API-positive mode ionization data from the HPLC-MS analysis of extracts of B. graminis [nasAB] cultures fed with either A) nothing, B) 1,2-13C2-labelled L-leucine or C) isopropyl-D7-labelled L-leucine.
Figure 4
Figure 4
Putative nasB homolgs from sequenced bacterial genomes are found in a variety of genetic contexts. The labels for nasB homologs are taken from the corresponding KEGG database entries. The GenBank Accession Numbers for CAP2UW1_1243, Arad_3395 and STHERM_c19760 are ACV34571, ACM27363 and ADN02911, respectively.
Scheme 1
Scheme 1
A) The proposed condensation of 2-oxoisocaproic acid (8) and malonyl-ACP (9) by nasB to form 5-methyl-3-oxohexanoyl-ACP (10). B) Scheme for the biosynthesis of N-(11-methyldodecanoyl)-phenylalanine (6), beginning with the FAS II-mediated chain elongation of 10, yielding 11-methyldodecanoyl-ACP (11).
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