Structure of Bacitracin A

Abstract

REPORTS in the literature1 regarding the dodecapeptide, bacitracin A, indicate the presence in the molecule of the sequences phenylalanyl histidine (I) and phenylalanyl isoleucyl cysteine (II). Two related facts remain unexplained: (a) there is only one phenylalanine residue in the molecule; hence it is the same phenylalanyl which is present in (I) and (II); (b) on total hydrolysis of dinitrophenyl–bacitracin A, the dinitrophenyl derivative of the isoleucine residue in (II) can be isolated, though in poor yield1.

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References

  1. 1

    Lockhart, I. M., and Abraham, E. P., Biochem. J., 58, 633 (1954). Lockhart, I. M., Abraham, E. P., and Newton, G. G. F., ibid., 61, 534 (1955). Hausmann, W., Weisiger, J. R., and Craig, L. C., J. Amer. Chem. Soc., 77, 723 (1955). Lockhart, I. M., and Abraham, E. P., Biochem. J., 62, 645 (1956).

  2. 2

    Wrinch, D., Nature, 137, 411 (1936) et seq.; Proc. Roy. Soc., A, 160, 59 (1937) et seq.; Phil. Mag., 31, 183 (1941), etc.

  3. 3

    Stoll, A., Hoffman, A., and Petrzilka, T., Helv. Chim. Acta, 34, 1544 (1951).

  4. 4

    Stoll, A., “Prog. in Chem. of Org. Nat. Products”, 8, 114 (1952).

  5. 5

    Cf. also Gaylord, N. G., Exper., 10, 351 (1954).

  6. 6

    In this structure, R is C15H15N2, the lysergic acid residue. Residue two is L-phenylalanyl for ergotamine and ergocristine, L-leucyl for ergosine and ergokryptine and L-valyl for ergocornine. R1 is methyl for ergotamine and ergosine and CHMe2 in the three other cases. The third residue (prolyl in all cases) is also in the L-form.

  7. 7

    Glenn, A. L., Quart. Rev. Chem. Soc., Lond., 8, 192 (1954).

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WRINCH, D. Structure of Bacitracin A. Nature 179, 536–537 (1957). https://doi.org/10.1038/179536a0

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