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Gas chromatographic determination of the configuration of isovaline in antiamoebin, samarosporin (emerimicin IV), stilbellin, suzukacillins and trichotoxins

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Summary

The D-(resp. R) configuration of isovaline (=2-ethylalanine) was proved for the peptide antibiotics antiamoebin, Tü 165 (CBS 382.62), stilbellin, samarosporin (=emerimicin IV), suzukacillin B (A), trichotoxin A-40 and A-50. This contradicts the previously reported L-configuration for isovaline in antiamoebin and emerimicin IV. The configuration was determined by GC of the N-trifluoroacetyl-isovaline n-propyl ester on glass capillary columns coated with the chiral stationary phase N-propionyl-L-valine tert.-butylamide polysiloxane (Chirasil Val). The D-configuration of the isovaline from trichotoxin A-40 was also established independently using GC of N-pentafluoro-propionyl-isovaline (+)-3-methyl-2-butyl esters on glass capillary columns coated with OV 17.

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Authors and Affiliations

  1. Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, D-7400, Tübingen 1, Federal Republic of Germany

    H. Brückner, G. J. Nicholson & G. Jung

  2. Institut für Organische Chemie und Biochemie der Universität Hamburg, Martin-Luther-King-Platz 6, D-2000, Hamburg 13, Federal Republic of Germany

    K. Kruse & W. A. König

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  1. H. Brückner
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  2. G. J. Nicholson
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  3. G. Jung
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  4. K. Kruse
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  5. W. A. König
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Brückner, H., Nicholson, G.J., Jung, G. et al. Gas chromatographic determination of the configuration of isovaline in antiamoebin, samarosporin (emerimicin IV), stilbellin, suzukacillins and trichotoxins. Chromatographia 13, 209–214 (1980). https://doi.org/10.1007/BF02261873

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