Trypanothione

Base Information

• Chemical Name: Trypanothione
• CAS No.: 96304-42-6
• Molecular Formula: C₂₇H₄₇N₉O₁₀S₂
• Molecular Weight: 721.856
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70242197
• Nikkaji Number: J634.980C
• Wikipedia: Trypanothione
• Wikidata: Q7848584
• Metabolomics Workbench ID: 52126
• Mol file: 96304-42-6.mol

Synonyms:dethiotrypanothione;N(1),N(8)-bis(gamma-Glu-hemi-Cys-Gly)sperimidine;N(1),N(8)-bis(gamma-glutamyl-hemicystinyl-glycyl)spermidine;trypanothione

Chemical Property of Trypanothione

Chemical Property:

• Boiling Point: 1284.7 °C at 760 mmHg
• Flash Point: 730.8 °C
• PSA: 363.87000
• Density: 1.41 g/cm³
• LogP: -0.21370
• Storage Temp.: Store at 0°C
• XLogP3: -9.2
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 10
• Exact Mass: 721.28873108
• Heavy Atom Count: 48
• Complexity: 1120

Purity/Quality:

99% ^*data from raw suppliers

Trypanothione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCNC(=O)CNC(=O)C(CSSCC(C(=O)NCC(=O)NCCCNC1)NC(=O)CCC(C(=O)O)N)NC(=O)CCC(C(=O)O)N
• Isomeric SMILES: C1CCNC(=O)CNC(=O)[C@H](CSSC[C@@H](C(=O)NCC(=O)NCCCNC1)NC(=O)CC[C@@H](C(=O)O)N)NC(=O)CC[C@@H](C(=O)O)N
• Uses: A major function of trypanothione is in the defence against oxidative stress. Trypanothione-dependent enzymes such as tryparedoxin peroxidase (TryP) reduce peroxides using electrons donated either directly from trypanothione, or via the redox intermediate tryparedoxin.

Technology Process of Trypanothione

There total 18 articles about Trypanothione 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:

N-α-tert-butoxycarbonyl-L-glutamic acid γ-N-succinimidyl ester α-tert-butyl ester (81659-82-7) → trypanothione disulfide (96304-42-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / dimethylformamide / 10 h / Ambient temperature

2: 80 percent / dicyclohexylcarbodiimide / tetrahydrofuran / 8 h / 4 °C

3: dimethylformamide / 8 h / 4 °C

4: TFA / 1 h / Ambient temperature

5: aq. dithiothreitol

6: O₂ / ethyl acetate / 48 h / 4 °C

With oxygen; dicyclohexyl-carbodiimide; trifluoroacetic acid; diothiothreitol; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c39860000593

Reference yield:

N1,N8-bis(glutathionyl)spermidine (109658-48-2) → trypanothione disulfide (96304-42-6)

Guidance literature:

With oxygen; In ethyl acetate; at 4 ℃; for 48h; Yield given;

DOI:10.1039/c39860000593

Reference yield:

Boc-L-glutamyl-α-t-butyl-τ-(S-t-butylmercaptocysteine) (104199-69-1) → trypanothione disulfide (96304-42-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / DCC / tetrahydrofuran / 12 h / Ambient temperature

2: 1) H₂ / 1) Pd/C / 1) EtOH, 1h, 2) DMF, 12h

With hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran;

upstream raw materials:

N¹,N⁸-bis(glutathionyl)spermidine

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine

Refernces

• 1、 Orban, Oliver C.F.,Korn, Ricarda S.,Benítez, Diego,Medeiros, Andrea,Preu, Lutz,Loa?c, Nadège,Meijer, Laurent,Koch, Oliver,Comini, Marcelo A.,Kunick, Conrad. "5-Substituted 3-chlorokenpaullone derivatives are potent inhibitors of Trypanosoma brucei bloodstream forms". . p. 3790 - 3800. Retrieved 2016/07/20.
• 2、 Henderson, Graeme B.,Glushka, John,Cowburn, David,Cerami, Anthony. "Synthesis and NMR Characterization of the Trypanosomatid Metabolite, N1,N8-Bis(glutathionyl)spermidine Disulphide (Trypanothione Disulphide)". . p. 911 - 914. Retrieved 2007/10/02.