Title: Sedecamycin
CAS Registry Number: 23477-98-7
CAS Name: (2S)-N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-13-(Acetyloxy)-7-hydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxopropanamide
Additional Names: N-(7,13-dihydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl)pyruvamide 13-acetate; Antibiotic T-2636A; bundlin B; lankacidin A; lankacidin C 14-acetate
Manufacturers' Codes: T-2636A
Trademarks: Takelan (Takeda)
Molecular Formula: C27H35NO8
Molecular Weight: 501.57
Percent Composition: C 64.65%, H 7.03%, N 2.79%, O 25.52%
Literature References: One of 7 components of antibiotic T-2636. First isolated as bundlin B from Streptomyces griseofuscus: J. M. J. Sakamoto et al., J. Antibiot. A15, 98 (1962). Isoln from S. rochei var volubilis: NL 6807119; E. Higashide et al., US 3626055 (1968, 1971 both to Takeda); eidem, J. Antibiot. 24, 1 (1971); S. Harada et al., ibid. 13. Similar to lankacidin which is isolated from S. violaceoniger with lankamycin. Structure, absolute configuration and identity with bundlin B: H. Harada et al., Tetrahedron Lett. 10, 2239 (1969); K. Kamiya et al., ibid. 2245; M. Uramoto et al., ibid. 2249. Enzymatic conversion to other lankacidins: T. Fugono et al., Experientia 26, 26 (1970). Antibacterial activity: K. Tsuchiya et al., J. Antibiot. 24, 29 (1971). Mass spectra: M. Uramoto et al., Agric. Biol. Chem. 38, 855 (1974). Biosynthetic studies: eidem, J. Am. Chem. Soc. 100, 3616 (1978); K. Kakinima et al., Tetrahedron Lett. 23, 5303 (1982). Synthetic study: M. J. Fray, E. J. Thomas, Tetrahedron 40, 673 (1984). Activity against Treponema hyodysenteriae (swine dysentery): BE 891275; N. Narukawa et al., US 4425356 (1982, 1984 both to Takeda).
Properties: Neutral lipophilic colorless plates from ether-ethyl acetate, mp 207-210° (dec). [a]D25 -235° (c = 1.0 in ethanol). uv max (ethanol): 228 mu (e 46900). Slightly sol in n-hexane, petroleum ether. Sol in ethyl acetate, acetone, chloroform, methanol. LD50 in mice (g/kg): up to 10 orally, 8-10 i.p. (Harada).
Melting point: mp 207-210° (dec)
Optical Rotation: [a]D25 -235° (c = 1.0 in ethanol)
Absorption maximum: uv max (ethanol): 228 mu (e 46900)
Toxicity data: LD50 in mice (g/kg): up to 10 orally, 8-10 i.p. (Harada)
Therap-Cat-Vet: Antibacterial. In swine dysentery.
Status: This monograph has been retired and is no longer subject to revision or update. |