Fatty acids of the genus Bacillus: an example of branched-chain preference.

Abstract

nally methyl-branched fatty acids, 13-methyltetradecanoic (iso-C15) and 15-methylhexadecanoic (iso-C,7), in Bacillus subtilis (natto) (138), and 12-methyltetradecanoic (anteiso-C,5) acid in a species of Sarcina (4), was first reported. After these reports, extensive studies conducted in my laboratory led to the discovery of three additional branched-chain fatty acids; 12methyltridecanoic (iso-C14), 14-methylpentadecanoic (iso-C16), and 14-methylhexadecanoic (anteiso-C,7) acids in the lipids of B. subtilis (76). These branched-chain acids are grouped in three series, based on their biosynthetic relationships (28, 77, 79, 80, 92, 102, 119) (Fig. 1). The definitions of iso and anteiso permit only iso methyl-substituted fatty acids (an iso ethyl would be an anteiso methyl of one-higher chain number), but would allow both methyl and ethyl as anteiso substitutions. Only the methyl anteiso substituent has so far been found in 391

Lipoproteins in bacteria: structures and biosynthetic pathways

“…This structure was named the 'N-acetyl form'. The determined fatty acid positions of the S-glyceryl group were consistent with published data on Bacillus phospholipids [42]. Similar analyses demonstrated the presence of the same N-acetyl form in another B. licheniformis lipoprotein OppA (Table 1).…”

Genetic engineering of the branched fatty acid metabolic pathway of Bacillus subtilis for the overproduction of surfactin C14 isoform

“…B. subtilis contains high percentage of branched chain FA in comparison to straight FA irrespective of medium conditions [17,18]. The β-OH fatty acid of the surfactin can be iso, anteiso or nC 13 ; iso or nC 14 , iso, anteiso or nC 15 and iso or nC 16 [2].…”

The effect of the growth medium composition on the fatty acids of Rhodothermus marinus and 'Thermus thermosphilus' HB-8

“…The (eu)bacteria which produce branchedchain fatty acid use isovaleryl-CoA, 2-methylbutyryl-CoA and isobutyryl-CoA as primers for the synthesis of iso-odd, anteiso-odd and iso-even 17 fatty acids, respectively, which can be derived from a-ketoacids of leucine, isoleucine and valine, respectively [13]. Presumably, medium A (yeast extract and tryptone) and medium C (yeast extract alone) lead to the synthesis of primers for odd-chain fatty acids, while in medium B (yeast extract and glutamate) higher pools of isobutyryl-CoA are produced, leading to even-chain fatty acids by the branched-chain fatty acid synthetase [14].…”

“…Since bacteria possessing branched-chain fatty acids have a branched fatty acid synthetase which does not effectively convert acetyl-CoA to acetyl-acyl carrier protein (acetyl-ACP), growth in medium D probably gives rise to high levels of malonyl-ACP which can be directly converted to acetyl-ACP leading to the synthesis of normal-chain fatty acids [11,15]. Alternatively, high levels of butyryl-CoA could serve as primer for normal-chain chain fatty acids by the branched-chain fatty acids synthetase [14]. While a large number of (eu)bacteria normally produce branched-chain fatty acids, some may, under specific growth conditions, as shown in this study, be capable of producing large relative proportions of normal-chain fatty acids.…”