TENTOXIN

Base Information

• Chemical Name: TENTOXIN
• CAS No.: 28540-82-1
• Molecular Formula: C₂₂H₃₀N₄O₄
• Molecular Weight: 414.505
• Hs Code.: 29337900
• Mol file: 28540-82-1.mol

Synonyms:Cyclo(N-methyl-L-alanyl-L-leucyl-a,b-didehydro-N-methylphenylalanylglycyl), (Z)-; Tentoxin(8CI); 1,4,7,10-Tetraazacyclododecane, cyclic peptide deriv.;Cyclic(N-methyl-L-alanyl-L-leucyl-a,b-didehydro-N-methylphenylalanylglycyl),(Z)-

Chemical Property of TENTOXIN

Chemical Property:

• Vapor Pressure: 2E-22mmHg at 25°C
• Boiling Point: 750.8°Cat760mmHg
• Flash Point: 407.9°C
• PSA: 98.82000
• Density: 1.114g/cm³
• LogP: 1.52690
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

Tentoxin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: tentoxin, a highly effective phytotoxin from Alternaria alternata f. sp. tenuis, is too expensive to be used as a commercial herbicide (80). Efforts to discover a cheaper, synthetic analogue of tentoxin with similar herbicidal properties have failed. Tentoxin is a cyclic tetrapeptide first isolated from the plant pathogen A. alternata. It is an herbicide that inhibits chloroplast development, resulting in chlorotic tissue. Tentoxin is selectively phytotoxic, as it kills a number of important weeds at concentrations that have no effects on several important crops.
• Uses: Tentoxin, is a natural cyclic tetrapeptide, isolated from Alternaria alternata, which induces chlorosis in plants, and thus can be used as a potential natural herbicide.

Technology Process of TENTOXIN

There total 6 articles about TENTOXIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

((Z)-2-{Methyl-[(S)-4-methyl-2-((S)-2-methylamino-propionylamino)-pentanoyl]-amino}-3-phenyl-acryloylamino)-acetic acid → tentoxin (28540-82-1,64070-01-5,65452-16-6)

Guidance literature:

With 1,3-di-tert-butylcarbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 25 ℃; for 1.5h;

DOI:10.1021/ol0345273

Reference yield:

Fmoc-Leu-OH (35661-60-0) → tentoxin (28540-82-1,64070-01-5,65452-16-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPCDI; HOBt; DIEA / CH₂Cl₂; dimethylformamide / 1.5 h / 25 °C

With 1,3-di-tert-butylcarbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0345273

Reference yield:

Fmoc-β-OH-Phe-OH (487060-72-0) → tentoxin (28540-82-1,64070-01-5,65452-16-6)

Guidance literature:

Multi-step reaction with 2 steps

1: DIPCDI; HOBt; DIEA / CH₂Cl₂; dimethylformamide / 1.5 h / 25 °C

With 1,3-di-tert-butylcarbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0345273

upstream raw materials:

Methyl-N-Boc-N-methyl-L-Ala-L-Leu-N-methyl-(Z)-dehydroPhe-Glycinat

Fmoc-Leu-OH

Fmoc-β-OH-Phe-OH

Refernces

• 1、 Cavelier, Florine,Verducci, Jean. "New synthesis of the cyclic tetrapeptide tentoxin employing an azlactone as key intermediate". . p. 4425 - 4428. Retrieved 2007/10/02.