Validamycins
Title: Validamycins
Literature References: Antibiotic complex produced by Streptomyces hygroscopicus var limoneus. Consists of validamycins A (major component), B, C, D, E, and F. Isoln, characterization, and biological properties of validamycins A and B: Iwasa et al., J. Antibiot. 24, 107, 119 (1971). Isoln and characterization of validamycins C, D, E, F: Horii et al., ibid. 25, 48 (1972). Manuf: Horii et al., JP 72 39697 (1972 to Takeda), C.A. 78, 122657a (1973). Structure of validamycin A: Horii, Kameda, Chem. Commun. 1972, 747; revised structure: T. Suami et al., J. Antibiot. 33, 98 (1980). Bioassay methods: Iwasa et al., ibid. 24, 114 (1971). Total synthesis of (±)-validoxylamines A and B, constituents of validamycins: S. Ogawa et al., J. Org. Chem. 49, 2594 (1984). Total synthesis of validamycin B: S. Ogawa, Y. Miyamoto, Chem. Commun. 1987, 1843; of validamycin A: eidem, Chem. Lett. 1988, 889.
 
Derivative Type: Validamycin A
CAS Registry Number: 37248-47-8
CAS Name: [1S-(1a,4a,5b,6a)]-1,5,6-Trideoxy-4-O-b-D-glucopyranosyl-5-(hydroxymethyl)-1-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-D-chiro-inositol
Trademarks: Validacin (Takeda); Valimon (Takeda)
Molecular Formula: C20H35NO13
Molecular Weight: 497.49
Percent Composition: C 48.29%, H 7.09%, N 2.82%, O 41.81%
Properties: Colorless hydrophilic powder. Does not show sharp mp; softens at 100°, dec at 135°. [a]D24 +110° (c = 1 in water or pyridine), +92° (c = 1 in DMF). pKa 6.0. Sol in water, methanol, DMF, DMSO; sparingly sol in ethanol, acetone. Insol in ethyl acetate, diethyl ether.
pKa: pKa 6.0
Optical Rotation: [a]D24 +110° (c = 1 in water or pyridine), +92° (c = 1 in DMF)
 
Derivative Type: Hydrochloride
Molecular Formula: C20H35NO13.HCl
Molecular Weight: 533.95
Percent Composition: C 44.99%, H 6.80%, N 2.62%, O 38.95%, Cl 6.64%
Properties: Crystalline powder, mp 95° (dec). [a]D22 +49° (c = 1 in water). Sol in water, alcohols. Insol in acetone, diethyl ether.
Melting point: mp 95° (dec)
Optical Rotation: [a]D22 +49° (c = 1 in water)
 
Use: Fungicide.

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