122380-18-1

Basic information

• Product Name: THAXTOMINE A
• Synonyms: THAXTOMINE A;(3R,6S)-3-Hydroxy-3-[(3-hydroxyphenyl)methyl]-1,4-dimethyl-6-[(4-nitro-1H-indol-3-yl)methyl]-2,5-piperazinedione;MBI 005
• CAS NO: 122380-18-1
• Molecular Formula: C22H22N4O6
• Molecular Weight: 438.43
• Mol File: 122380-18-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 794.6 °C at 760 mmHg
• Flash Point: 434.3 °C
• Appearance: Orange solid.
• Density: 1.479 g/cm³
• Vapor Pressure: 1.27E-26mmHg at 25°C
• Refractive Index: 1.71
• Storage Temp.: -20°C
• CAS DataBase Reference: THAXTOMINE A(CAS DataBase Reference)
• NIST Chemistry Reference: THAXTOMINE A(122380-18-1)
• EPA Substance Registry System: THAXTOMINE A(122380-18-1)

Safety Data

• Hazardous Substances Data: 122380-18-1(Hazardous Substances Data)

Usage

Description

Thaxtomin A is a major phytotoxin produced by S. scabies, gram-positive soil bacterium responsible for producing scabs on tubers and root vegetables. This bacterial metabolite acts as a virulence factor in the common scab potato disease and demonstrates herbicidal activity against the dicotyledon weeds B. campestris and A. retroflexus.

Uses

Thaxtomin A is a phytotoxin produced by Streptomyces scabies and other Streptomyces species, the causative agents of common scab disease in potato and other taproot crops.

InChI:InChI=1/C22H22N4O6/c1-24-18(10-14-12-23-16-7-4-8-17(19(14)16)26(31)32)20(28)25(2)22(30,21(24)29)11-13-5-3-6-15(27)9-13/h3-9,12,18,23,27,30H,10-11H2,1-2H3/t18-,22+/m0/s1

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 4607-41-4 3-hydroxy-α-oxo-benzenepropanoic acid 
• 880087-62-7 ethyl 2-(4-nitro-1H-indol-3-yl)acetate 
• 1430721-49-5 (R)-methyl 2-((tert-butoxycarbonyl)(methyl)amino)-5-oxopentanoate 
• 861658-15-3 1,5-dimethyl (2R)-2-[[(tert-butoxy)carbonyl]amino]pentanedioate 
• 6893-26-1 D-Glutamic acid 

Relevant articles and documents

Total synthesis of thaxtomin A and its stereoisomers and findings of their biological activities

The first and facile total synthesis of thaxtomin A and its three stereoisomers has been achieved. The synthetic approach involves intramolecular nucleophilic cyclization of an amide toward a ketoamide group to produce a C-hydroxydiketopiperazine scaffold

Binding of Distinct Substrate Conformations Enables Hydroxylation of Remote Sites in Thaxtomin D by Cytochrome P450 TxtC

Cytochromes P450 (CYPs) catalyze various oxidative transformations in drug metabolism, xenobiotic degradation, and natural product biosynthesis. Here we report biochemical, structural, and theoretical studies of TxtC, an unusual bifunctional CYP involved in the biosynthesis of the EPA-approved herbicide thaxtomin A. TxtC was shown to hydroxylate two remote sites within the Phe residue of its diketopiperazine substrate thaxtomin D. The reactions follow a preferred order, with hydroxylation of the α-carbon preceding functionalization of the phenyl group. To illuminate the molecular basis for remote site functionalization, X-ray crystal structures of TxtC in complex with the substrate and monohydroxylated intermediate were determined. Electron density corresponding to a diatomic molecule (probably dioxygen) was sandwiched between the heme iron atom and Thr237 in the TxtC-intermediate structure, providing insight into the mechanism for conversion of the ferrous-dioxygen complex into the reactive ferryl intermediate. The substrate and monohydroxylated intermediate adopted similar conformations in the active site, with the ?€-face of the phenyl group positioned over the heme iron atom. Docking simulations reproduced this observation and identified a second, energetically similar but conformationally distinct binding mode in which the α-hydrogen of the Phe residue is positioned over the heme prosthetic group. Molecular dynamics simulations confirmed that the α-hydrogen is sufficiently close to the ferryl oxygen atom to be extracted by it and indicated that the two substrate conformations cannot readily interconvert in the active site. These results indicate that TxtC is able to hydroxylate two spatially remote sites by binding distinct conformations of the substrate and monohydroxylated intermediate.

Thaxtomin A and its stereoisomers of the synthesis method

The invention relates to Thaxtomin A and a synthesis method of a stereisomer of Thaxtomin A. The chemical constructions of Thaxtomin A and the stereisomer are as shown in the specification. The invention further provides a synthesis method of the stereisomer. The synthesis route has the characteristics of being efficient, and the stereisomer can be spliced by recrystallization, which is beneficial to mass production of target products.