Enduracidin

Title: Enduracidin
CAS Registry Number: 11115-82-5
Additional Names: Enramycin
Literature References: Cyclodepsipeptide antibiotic produced by Streptomyces fungicidicus, strain no. B5477, from a soil sample collected in Nishinomiya, Hyogo Prefecture, Japan: Higashide et al., J. Antibiot. 21, 126 (1968). Originally thought to be a single compound. Isoln and characterization: Asai et al., ibid. 138; FR 1514139; GB 1163270 (1968, 1969 to Takeda). Manufacturing process: JP Kokai 82 79896 (1982 to Takeda), C.A. 97, 108525s (1982). Separation into two components, enduracidins A and B: Hori et al., Chem. Pharm. Bull. 21, 1171 (1973). The two components are each composed of seventeen amino acids, sixteen of which form a macrocyclic peptide lactone, and only differ by one methylene group in their fatty acid moieties. Structural studies: Hori et al., ibid. 1175. Final structure: Iwasaki et al., ibid. 1184. Antibacterial activity: Goto et al., J. Antibiot. 21, 119 (1968); Tsuchiya et al., ibid. 147; M. Kawakami et al., ibid. 24, 583 (1971). Toxicology: H. Yokotani et al., Takeda Kenkyusho Nempo 28, 76 (1969), C.A. 72, 77300s (1970).
Derivative Type: Monohydrochloride
Trademarks: Enradin (Takeda)
Properties: Yellowish powder, dec 234-238°. Slightly sol in water, methanol. Practically insol in acetone, ethanol, chloroform, benzene. LD50 in mice and rats (mg/kg): >10000 orally; >5000 i.m.; >5000 s.c. (Yokotani).
Toxicity data: LD50 in mice and rats (mg/kg): >10000 orally; >5000 i.m.; >5000 s.c. (Yokotani)
Derivative Type: Enduracidin A hydrochloride
CAS Registry Number: 33368-20-6
Molecular Formula: C107H138Cl2N26O31.HCl
Molecular Weight: 2391.76
Percent Composition: C 53.73%, H 5.86%, Cl 4.45%, N 15.23%, O 20.74%
Properties: mp 240-245°. [a]D23 +92° (c = 0.5 in DMF). uv max (0.1N HCl): 231, 272 nm.
Melting point: mp 240-245°
Optical Rotation: [a]D23 +92° (c = 0.5 in DMF)
Absorption maximum: uv max (0.1N HCl): 231, 272 nm
Derivative Type: Enduracidin B hydrochloride
CAS Registry Number: 34765-98-5
Molecular Formula: C108H140Cl2N26O31.HCl
Molecular Weight: 2405.79
Percent Composition: C 53.92%, H 5.91%, Cl 4.42%, N 15.14%, O 20.62%
Properties: mp 238-241°. [a]D23 +92° (c = 0.5 in DMF). uv max (0.1N HCl): 231, 272 nm.
Melting point: mp 238-241°
Optical Rotation: [a]D23 +92° (c = 0.5 in DMF)
Absorption maximum: uv max (0.1N HCl): 231, 272 nm
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.
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