Isolement de l'acide 3-amino 12-methyl tetradecanoique et de l'acide 3-amino 12-methyl tridecanoique a partir de l'iturine,antibiotique de Bacillus subtilis |
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Authors: | F Peypoux M Guinand G Michel L Delcambe BC Das P Varenne E Lederer |
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Institution: | Laboratoire de Chimie Biologique, Université de Lyon I, 43, Boulevard du 11 Novembre 1918, 69621 Villeurbanne, France;Centre National de Production et d''Etude des Substances d''Origine Microbienne, 32 Boulevard de la Constitution, Liège, Belgique;Institut de Chimie des Substances Naturelles, C.N.R.S. 91190 Gif-sur-Yvette, France |
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Abstract: | lturin, a peptide antibiotic from Bacillus subtilis, was separated into three iturins: A, B, C by thin-layer chromatography. Iturin A, which has an antifungal activity, contains Asp, Glu, Tyr, Ser, Pro in a molar ratio 3:1:1:1:1 and a lipid moiety AL. The latter was shown to be a mixture of C14 (40%) and C15, (60%) amino-acids. The structure of these was determined by combined gas chromatography-mass spectrometry of the N-acetylmethyl esters. Strong peaks at m/e = 144 and m/e = 102 indicate a β-amino group. Identification of acetone and methylethylketone after chromic acid oxidation indicates an iso and anteiso structure. After comparison of the natural amino-acids with synthetic 3-amino pentadecanoic acid it is concluded that the lipid AL is a mixture of 3-amino 12- methyltetradecanoic acid and 3-amino 12-methyltridecanoic acid. |
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