Supplementary Information for. Biosynthesis of iso-fatty acids in myxobacteria
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1 Supplementary Material for Organic & Biomolecular Chemistry This journal is The Royal Society of Chemistry 2005 Supplementary Information for Biosynthesis of iso-fatty acids in myxobacteria Jeroen S. Dickschat, a Helge B. Bode, b Reiner M. Kroppenstedt, c Rolf Müller, b and Stefan Schulz* a a Institut für Organische Chemie, TU Braunschweig, Hagenring 30, Braunschweig, Germany. Fax: ; Tel: ; stefan.schulz@tu-bs.de. b Institut für Pharmazeutische Biotechnologie, Universität des Saarlandes, Geb. 8.1, Saarbrücken, Germany. c Deutsche Sammlung für Zellkulturen und Mikroorganismen (DSZM), Mascheroder Weg 1b, Braunschweig, Germany. 1. Results of fatty acid analysis Table 1 Fatty acid profile of Stigmatella aurantiaca wild-type strain (WT) and a bkd mutant (bkd) without any feeding, and of the bkd mutant after feeding of isobutyric acid (IBA) and isovaleric acid (IVA). Amounts are given in % of total area in GC. Compound WT bkd IBA IVA iso-11: iso-13: iso-14: iso-15: iso-15: iso-15:0 3OH iso-16: iso-16: iso-17:1 (ω 10 cis) iso-17:1 (ω 5 cis) iso-17: iso-17:0 3OH : :1 (ω 10 cis) : :1 (ω 10 cis) :1 (ω 5 cis) :1 (ω 5 cis) : :0 3OH :0 2OH : : :
2 Table 2 Fatty acid profile of Myxococcus xanthus wild-type strain (WT) and a bkd mutant (bkd) without any feeding, and of the bkd mutant after feeding of isobutyric acid (IBA) and isovaleric acid (IVA). Amounts are given in % of total area in GC. Compound WT bkd IBA IVA iso-13: iso-14: iso-15: iso-15: iso-15: iso-15:0 3OH iso-16: iso-16: iso-16: iso-17: iso-17:1 (ω 10 cis) iso-17:1 (ω 5 cis) iso-17: iso-17:0 2OH iso-17:0 3OH :0 3OH : : : :1 (ω 10 cis) :1 (ω 5 cis) : :1 (ω 10 cis) :1 (ω 5 cis) : :2 (ω 5 cis, ω 11 cis) :1 (ω 11 cis) :1 (ω 5 cis) : :0 3OH :0 2OH :1 (ω 10 cis) :1 (ω 5 cis) : Identification of methyl-branched fatty acid methyl esters by a retention index increment system Branched chain fatty acid methyl esters (FAMEs) have lower retention times in GC compared to their unbranched counterparts. The position of a methyl branch can be derived from the retention index of the methyl ester. Calculated retention indices I C of methyl-branched compounds with various functional groups (e. g. alkanes, 1 3-ketones or 3-alcohols 2 ) can be predicted by an increment system according to Equation 1. I C = N + FG + Me i + S (1) Herein N is the number of carbon atoms in the longest chain times one hundred, FG is a functional group increment, that is FG(ME) = 332 for methyl esters (BPX-5 fused silica capillary column) and Me i is an increment for the methyl group depending on its position. The different values for Me i are given in the literature, 1 and it is Me i = 60 for a methyl branch in ω 1 position. A steric increment S only has to be taken into account in case of multi methyl-branched compounds.
3 3. Identification of unsaturated fatty acids by derivatization with dimethyl disulfide (DMDS) The position of double bonds in unsaturated fatty acids cannot be derived from mass spectra, because the mass spectra of unsaturated fatty acid methyl esters only differing in the position of the double bond are very similar. The double bond position can be determined by derivatisation with dimethyl disulfide giving adducts as shown in Figure 1. These DMDS adducts show strong fragmentation between the two methylthio groups leading to the fragment ions A + and B +. Furthermore, the ion containing the methyl ester function is characterised by the loss of methanol giving ion C +. The mass spectra of DMDS adducts obtained from Stigmatella aurantiaca after feeding with [D 7 ]-15-methylhexadecanoic acid are shown in Figure 2. C + -MeOH A + O MeS O m n R SMe B + 14:1 (ω-5 cis): m=1, n=3, R=Me 16:1 (ω-5 cis): m=3, n=3, R=Me [D 7 ]iso 17:1 (ω-7 cis): m=1, n=4, R=[D 7 ]-ipr [D 7 ]iso 17:1 (ω-6 cis): m=2, n=3, R=[D 7 ]-ipr [D 7 ]iso 17:1 (ω-5 cis): m=3, n=2, R=[D 7 ]-ipr [D 7 ]iso 17:1 (ω-4 cis): m=4, n=1, R=[D 7 ]-ipr Fig. 1 Fragmentation of DMDS adducts of unsaturated fatty acid methyl esters in MS. Table 3 DMDS adducts obtained from a methylated fatty acid extract of Stigmatella aurantiaca fed with [D 7 ]-15-methylhexadecanoate. M + : molecular ion, A +, B +, C + : fragment ions in Figure 1. Parent Compound M + A + B + C + 14:1 (ω-5 cis) :1 (ω-5 cis) [D 7 ]iso-17:1 (ω-7 cis) [D 7 ]iso-17:1 (ω-6 cis) a [D 7 ]iso-17:1 (ω-5 cis) a [D 7 ]iso-17:1 (ω-4 cis) a a DMDS derivatives coelute in GC (compare Figure 2D).
4 Fig. 2 DMDS adducts of unsaturated fatty acids obtained from Stigmatella aurantiaca after feeding with [D 7 ]- 15-methylhexadecanoic acid. (A) 14:1 (ω-5, cis), (B) 16:1 (ω-5, cis), (C) [D 7 ]iso-17:0 (ω-4, cis), (D) coeluting [D 7 ]iso-17:0 (ω-5, cis), [D 7 ]iso-17:0 (ω-6, cis), and [D 7 ]iso-17:0 (ω-7, cis).
5 References 1 S. Schulz, Lipids, 2001, 36, J. S. Dickschat, S. C. Wenzel, H. B. Bode, R. Müller, S. Schulz, ChemBioChem, 2004, 4,
A novel biosynthetic pathway providing precursors for fatty acid biosynthesis and secondary metabolite formation in myxobacteria
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