Title: Trichostatin(s)
Additional Names: Antibiotic A-300; A-300-I
Literature References: Antifungal antibiotic isolated from metabolites of Streptomyces hygroscopicus. It is composed of trichostatins A (major), B, the ferric chelate of trichostatin A, and C, the first glycosyl hydroxamate from a natural source. Isoln of A and B: N. Tsuji et al., JP Kokai 74 14691, C.A. 81, 48547h (1974). Structural elucidation of A and B: eidem, J. Antibiot. 29, 1 (1976). Isoln and structure of C: N. Tsuji, M. Kobayashi, ibid. 31, 939 (1978).
Derivative Type: Trichostatin A
CAS Registry Number: 58880-19-6
CAS Name: [R-(E,E)]-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide
Molecular Formula: C17H22N2O3
Molecular Weight: 302.37
Percent Composition: C 67.53%, H 7.33%, N 9.26%, O 15.87%
Properties: Crystals from ethyl acetate, mp 150-151°. [a]D20.5 +62.8° ±1.1° (c = 1.007 in ethanol). uv max (ethanol): 252, 265, 341 nm (E1%1cm 531, 582, 648). Sol in lower alcohols, sparingly sol in chloroform, ethyl acetate, acetone, benzene.
Melting point: mp 150-151°
Optical Rotation: [a]D20.5 +62.8° ±1.1° (c = 1.007 in ethanol)
Absorption maximum: uv max (ethanol): 252, 265, 341 nm (E1%1cm 531, 582, 648)
Derivative Type: Trichostatin B
CAS Registry Number: 58895-00-4
CAS Name: Tris[7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamidato-ONO1]iron
Molecular Formula: C51H63FeN6O9
Molecular Weight: 959.93
Percent Composition: C 63.81%, H 6.62%, Fe 5.82%, N 8.75%, O 15.00%
Properties: Trihydrate, dark reddish purple prisms from methanol, mp 192° (dec). uv max (ethanol): 253, 277, 341, 450 nm (E1%1cm 624, 651, 918, 50).
Melting point: mp 192° (dec)
Absorption maximum: uv max (ethanol): 253, 277, 341, 450 nm (E1%1cm 624, 651, 918, 50)
Derivative Type: Trichostatin C
CAS Registry Number: 68676-88-0
CAS Name: 7-[4-(Dimethylamino)phenyl]-N-(b-D-glucopyranosyloxy)-4,6-dimethyl-7-oxo-2,4-heptadienamide
Molecular Formula: C23H32N2O8
Molecular Weight: 464.51
Percent Composition: C 59.47%, H 6.94%, N 6.03%, O 27.55%
Properties: Colorless prisms from methanol, mp 171-173°. [a]D24 +50.5 ±0.9° (c = 0.987 in methanol). uv max (methanol): 268, 344 nm (e 14600; 14300).
Melting point: mp 171-173°
Optical Rotation: [a]D24 +50.5 ±0.9° (c = 0.987 in methanol)
Absorption maximum: uv max (methanol): 268, 344 nm (e 14600; 14300)
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