9910. Valinomycin
Nomenclature
Description and references
Cyclododecadepsipeptide ionophore antibiotic produced by Streptomyces fulvissimus and related to the enniatins, q.v. Composed of 3 moles each of l-valine, d-α-hydroxyisovaleric acid, d-valine, and l-lactic acid linked alternately to form a 36-membered ring: Brockmann et al., Ber. 88, 57 (1955); Ann. 603, 216 (1957). Structural studies: Shemyakin et al., Tetrahedron Lett. 1963, 351; Tetrahedron 19, 995 (1963). Proposed structure: Brockmann et al., Naturwissenschaften 50, 689 (1963). Structure and synthesis: Shemyakin et al., Tetrahedron Lett. 1963, 1921. Solid phase synthesis: Gisin et al., J. Am. Chem. Soc. 91, 2691 (1969); Losse, Klengel, Tetrahedron 27, 1423 (1971). Biosynthesis: Smirnova et al., C.A. 73, 97347m (1970); Ristow et al., FEBS Lett. 42, 127 (1974). Conformation: Ivanov et al., Biochem. Biophys. Res. Commun. 34, 803 (1969); Onishi, Urry, ibid. 36, 194 (1969); Duax et al., Science 176, 911 (1972). Review: Y. A. Ovchinnokov, V. T. Ivanov, “The Cyclic Peptides: Structure, Conformation, and Function”, in The Proteins vol. V, H. Neurath, R. L. Hill, Eds. (Academic Press, New York, 3rd ed., 1982) pp 563-573.
