Title: Detoxin Complex
Additional Names: DX.C
Literature References: A group of selective antagonists of blasticidin S, q.v., produced by Streptomyces caespitosus var. detoxicus 7072 GC1. The complex counteracts the inhibitory action of blasticidin S (BS) against Bacillus cereus but not against Piricularia oryzal, the causative agent of rice blast disease. DX.C also depresses the phytotoxicity of BS to rice plants, and a combination of the two showed less eye irritation in animals than BS alone. Isoln, production, biological properties: H. Yonehara et al., J. Antibiot. 21, 369 (1968); eidem, Agric. Biol. Chem. 37, 2771 (1973). Separation of the complex yields eight groups of detoxins designated A through H, the major components being C and D: N. Otake et al., J. Antibiot. 21, 371 (1968); eidem, Agric. Biol. Chem. 37, 2777 (1973). Detoxin D1, the major component of the D group, has been shown to have the highest specific activity. It is a unique depsipeptide containing the amino acid detoxinine (b,3-dihydroxy-2-pyrrolidinepropanoic acid). Structure of D1: K. Kakenuma et al., Tetrahedron Lett. 1972, 2509. 13C-NMR: T. Ogita et al., Agric. Biol. Chem. 42, 2403 (1978). Structures of the minor components of the D group: N. Otake et al., J. Antibiot. 27, 484 (1974). Structures of detoxins A1, B1, B3, C1, C2, C3, E1: N. Otake et al., Experientia 37, 926 (1981); T. Ogita et al., Agric. Biol. Chem. 45, 2605 (1981). Effect of D on BS uptake in B. cereus: A. Shimazu et al., Experientia 37, 365 (1981).
Properties: Light colored fine powder.
Derivative Type: Detoxin D1
CAS Registry Number: 37878-19-6
CAS Name: N-(2-Methyl-1-oxobutyl)-L-phenylalanine (1S)-1-[(2S,3R)-3-(acetyloxy)-1-[(2S)-2-amino-3-methyl-1-oxobutyl]-2-pyrrolidinyl]-2-carboxyethyl ester
Molecular Formula: C28H41N3O8
Molecular Weight: 547.64
Percent Composition: C 61.41%, H 7.55%, N 7.67%, O 23.37%
Properties: Fine crystalline powder, mp 156-158°. [a]D25 -16° (c = 1 in methanol). uv max (methanol): 253, 258, 265, 268 nm (E1%1cm 3.1, 3.58, 2.77, 1.85). Amphoteric. pKa 4.0, 8.0.
Melting point: mp 156-158°
pKa: pKa 4.0, 8.0
Optical Rotation: [a]D25 -16° (c = 1 in methanol)
Absorption maximum: uv max (methanol): 253, 258, 265, 268 nm (E1%1cm 3.1, 3.58, 2.77, 1.85)
Derivative Type: Detoxin C1
CAS Registry Number: 74717-53-6
CAS Name: N-Acetyl-L-phenylalanine (1S)-1-[(2S,3R)-3-(acetyloxy)-1-[(2S)-2-amino-3-methyl-1-oxobutyl]-2-pyrrolidinyl]-2-carboxyethyl ester
Additional Names: detoxin Ca1
Molecular Formula: C25H35N3O8
Molecular Weight: 505.56
Percent Composition: C 59.39%, H 6.98%, N 8.31%, O 25.32%
Properties: Microneedles from water, mp 142-144°. Amphoteric. pKa 8.0, 3.9. [a]D25 -23° (c = 1 in methanol). uv max (methanol): 248, 253, 259, 265, 269 nm (E1%1cm 3.7, 3.18, 2.65, 2.8, 1.85).
Melting point: mp 142-144°
pKa: pKa 8.0, 3.9
Optical Rotation: [a]D25 -23° (c = 1 in methanol)
Absorption maximum: uv max (methanol): 248, 253, 259, 265, 269 nm (E1%1cm 3.7, 3.18, 2.65, 2.8, 1.85)
Use: In mixtures with blasticidin S, to decrease phytotoxicity to rice plants. |