Structural Formula Vector Image
Title: Subtilin
CAS Registry Number: 1393-38-0
Literature References: Polypeptide antibiotic structurally similar to nisin, q.v., but contains no methionine. Produced by Bacillus subtilis (NRRL no. B-543): E. F. Jansen, D. J. Hirshmann, Arch. Biochem. 4, 297 (1944); Lewis et al., ibid. 14, 415 (1947); Dimick et al., ibid. 15, 1 (1947). Isoln by partition chromatography on silica gel: Alderton, Snell, J. Am. Chem. Soc. 81, 701 (1959). Early structural studies: Stracher, Craig, ibid. 696. Structure is a heterodetic pentacyclic peptide consisting of 32 amino acid residues and containing unusual amino acids such as lanthionine, b-methyllanthionine, D-alanine, dehydroalanine and dehydrobutyrine: E. Gross et al., Z. Physiol. Chem. 354, 810 (1973). Biosynthetic studies: C. Nishio et al., Biochem. Biophys. Res. Commun. 116, 751 (1983); S. Banerjee, J. N. Hansen, J. Biol. Chem. 263, 9508 (1988).
Properties: Amorphous powder. [a]D23 -29 to -35° (c = 1 in 1% acetic acid). Diffuses quickly through cellophane. Readily sol in dilute acids; sparingly sol (less than 5 mg/ml) in water at pH 6-9. Sol in methanol, 80% alc. Soly in butanol satd with water: about 5 mg/ml. Easily salted out of soln by NaCl.
Optical Rotation: [a]D23 -29 to -35° (c = 1 in 1% acetic acid)
Use: Food preservative.

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