Title: Polyoxins
CAS Registry Number: 11113-80-7
Literature References: Agricultural antifungal antibiotic complex produced by Streptomyces cacaoi var asoensis and S. piomogenus. Polyoxins A through O are known, all except C and I having specific activity against phytopathogenic fungi by inhibiting cell wall chitin synthesis. Isoln and characterization of polyoxin A: S. Suzuki et al., J. Antibiot. 18A, 131 (1965); of A and B: K. Isono et al., Agric. Biol. Chem. 29, 848 (1965); S. Suzuki et al., JP 66 15520; of C through L: K. Isono et al., Agric. Biol. Chem. 30, 817 (1966); 31, 190 (1967); 32, 792 (1968); of M: K. Isono, S. Suzuki, Tetrahedron Lett. 1970, 425. Isoln of polyoxins N and O: S. Suzuki et al., JP Kokai 72 23596 (to Inst. Phys. Chem. Res., and Hokko Chem. Ind.), C.A. 78, 41566t (1973); production of N and O: eidem, JP 77 20555 (1977 to Inst. Phys. Chem. Res.), C.A. 87, 150183x (1977). Isoln and structure of N: M. Uramoto et al., Nucleic Acids Res. Spec. Publ. 5, 327 (1978). Structural elucidation of polyoxins A through L: K. Isono et al., J. Am. Chem. Soc. 91, 7490 (1969). Revised structure of A: S. Hanessian et al., Tetrahedron Lett. 34, 4153 (1993). Total synthesis of J: H. Kuzuhara et al., ibid. 1973, 5055. Biosynthetic studies: K. Isono et al., Biochemistry 14, 2992 (1975); S. Funayama, K. Isono, ibid. 5568; K. Isono, R. J. Suhadolnick, Arch. Biochem. Biophys. 173, 141 (1976); S. Funayama, K. Isono, Biochemistry 16, 3121 (1977); K. Isono et al., J. Am. Chem. Soc. 100, 3937 (1978). Mode of action: N. Ohta et al., Agric. Biol. Chem. 34, 1224 (1970); M. Hori et al., ibid. 35, 1280 (1971); 38, 691, 699 (1974). Review: R. J. Suhadolnick, Nucleoside Antibiotics (Wiley-Interscience, New York, 1970) pp 218-234; K. Isono, S. Suzuki, Heterocycles 13, 333-351 (1979).
Derivative Type: Polyoxin A
CAS Registry Number: 19396-03-3
CAS Name: [S-(Z)]-1-[5-[[2-Amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1,5-dideoxy-1-[3,4-dihydro-5-(hydroxymethyl)2,4-dioxo-1(2H)-pyrimidinyl]-b-D-allofuranuronoyl]-3-ethylidene-2-azetidinecarboxylic acid
Molecular Formula: C23H32N6O14
Molecular Weight: 616.53
Percent Composition: C 44.81%, H 5.23%, N 13.63%, O 36.33%
Properties: Colorless needles from aq ethanol, dec >180°. [a]D20 -30°. uv max (0.05N HCl): 262 nm (log e 3.94); (0.05N NaOH): 264 nm (log e 3.80).
Optical Rotation: [a]D20 -30°
Absorption maximum: uv max (0.05N HCl): 262 nm (log e 3.94); (0.05N NaOH): 264 nm (log e 3.80)
Derivative Type: Polyoxin B
CAS Registry Number: 19396-06-6
CAS Name: 5-[[2-Amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1,5-dideoxy-1-[3,4-dihydro-5-(hydroxymethyl)-2,4-dioxo-1(2H)-pyrimidinyl]-b-D-allofuranuronic acid
Additional Names: Polyoxin AL
Molecular Formula: C17H25N5O13
Molecular Weight: 507.41
Percent Composition: C 40.24%, H 4.97%, N 13.80%, O 40.99%
Properties: Amorphous powder from aq ethanol. [a]D20 +34°. uv max (0.05N HCl): 262 nm (log e 3.94); (0.05N NaOH): 264 nm (log e 3.82).
Optical Rotation: [a]D20 +34°
Absorption maximum: uv max (0.05N HCl): 262 nm (log e 3.94); (0.05N NaOH): 264 nm (log e 3.82)
Use: Fungicide, esp for Alternaria leaf spot of many agricultural products. |