Nomenclature
CAS number: 12704-90-4
(α
S,2
R,3
R,4
R,6
S)-
N-[(2
E,4
E,6
S,7
R)-7-[(2
S,3
S,4
R,5
R)-5-[(1
E,3
E,5
E)-7-(1,2-Dihydro-4-hydroxy-1-methyl-2-oxo-3-pyridinyl)-6-methyl-7-oxo-1,3,5-heptatrien-1-yl]tetrahydro-3,4-dihydroxy--2-furanyl]-6-methoxy-5-methyl-2,4-octadien-1-yl]-α-ethyltetrahydro-2,3,4-trihydroxy-5,5-dimethyl-6-(1
E,3
Z)-1,3-pentadien-1-yl-2
H-pyran-2-acetamide; 1-methylmocimycin; antibiotic X-5108; goldinodox; goldinomycin; X-5108.
C
44H
62N
2O
12; mol wt 810.97.
C 65.17%, H 7.71%, N 3.45%, O 23.67%.
Description and references
Antibiotic produced by Streptomyces goldiniensis var. goldiniensis: J. Berger, DE 2140322; idem, US 3708577 (1972, 1973 both to Hoffmann-La Roche). Isoln, production,
properties and toxicity data: J. Berger et al., J. Antibiot. 26, 15 (1973). Improved
production: J. Unowsky, D. C. Hoppe, ibid. 31, 662 (1978). Structure: H. Maehr et al., J. Am. Chem. Soc. 95, 8449 (1973). Absolute stereochemistry: eidem, ibid. 96, 4034 (1974). Biosynthesis:
C.-M. Liu et al., J. Antibiot. 30, 416 (1977); 32, 414 (1979). Stereospecific
total synthesis: R. E. Dolle, K. C. Nicolaou, J. Am. Chem. Soc. 107, 1691, 1695 (1985).
Growth promoting activity: W. L. Marusich et al., Poult. Sci. 53, 636 (1974). Review
of chemistry: H. Maehr et al., Can. J. Chem. 58, 501 (1980).
Properties
Yellow amorphous solid. Weakly acidic. Sol in
methanol, ethyl acetate, CHCl3, acetone, methylene chloride.
Insol in water. pKa = 6.1. Unstable in acidic or basic soln, but can be kept in aq soln
at pH 7-9 for 4 hrs at 25° without significant loss of activity.
Solns kept at 25° or heated to 56° are 2-10 times more stable in methanol
than in water or pH 9 borate buffer. LD50 in mice (mg/kg): >1000 s.c., >4000 orally (Berger et al.).Derivative
Sodium salt.
Nomenclature
CAS number: 74219-54-8
C
44H
61N
2NaO
12; mol wt 832.95.
C 63.45%, H 7.38%, N 3.36%, Na 2.76%, O 23.05%.
Properties
Yellow solid. [α]D25 82.8° (c = 0.52 in ethanol). uv max (0.1N HCl): 334, 233, 206 nm (E1%1cm 403, 610, 500); (0.1N KOH): 327, 231 nm (E1%1cm 416, 647). Sol in water, methanol, ethanol, isopropanol, butanol, DMF. Slightly
sol in amyl alcohol, THF, dioxane. Insol in benzene, chloroform,
ethyl ether, petr ether.