(2S,3S)-1,4-Dimercaptobutane-2,3-diol

Base Information

• Chemical Name: (2S,3S)-1,4-Dimercaptobutane-2,3-diol
• CAS No.: 3483-12-3
• Deprecated CAS: 1377983-58-8,27565-41-9,28823-08-7
• Molecular Formula: C₄H₁₀O₂S₂
• Molecular Weight: 154.254
• Hs Code.: 29309099
• European Community (EC) Number: 222-468-7,248-531-9
• DSSTox Substance ID: DTXSID5041017
• Nikkaji Number: J64.633D
• Wikipedia: Dithiothreitol
• Wikidata: Q414783
• NCI Thesaurus Code: C76286
• Metabolomics Workbench ID: 52308
• ChEMBL ID: CHEMBL1232392
• Mol file: 3483-12-3.mol

Synonyms:Cleland Reagent;Cleland's Reagent;Clelands Reagent;Dithiothreitol;Reagent, Cleland;Reagent, Cleland's;Sputolysin

Chemical Property of (2S,3S)-1,4-Dimercaptobutane-2,3-diol

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.019-0.29Pa at 20-50℃
• Melting Point: 41-44 °C(lit.)
• Refractive Index: 1.576
• Boiling Point: 364.453 °C at 760 mmHg
• PKA: pK1:8.9 (25°C)
• Flash Point: 174.215 °C
• PSA: 118.06000
• Density: 1.303 g/cm³
• LogP: -0.43220
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: freely soluble
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 154.01222190
• Heavy Atom Count: 8
• Complexity: 52

Purity/Quality:

99.0% ^*data from raw suppliers

Dithiothreitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 25-36/37/38-22-20/21/22
• Safety Statements: 26-45-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research,Other Classes -> Sulfur Compounds (Alcohols)
• Canonical SMILES: C(C(C(CS)O)O)S
• Isomeric SMILES: C([C@H]([C@@H](CS)O)O)S
• Uses: Dithiothreitol is a redox reagent commonly used as a reducing agent for thiolated DNA. Dithiothreitol is also used to reduce the disulfide bonds of proteins. DL-dithiothreitol (DTT) is a sulfhydryl compound that acts both as a reagent reducing disulfide bonds and as a protein denaturant on staphylococcal biofilm (Wu et al. 2011). Thanks to these properties, DTT is routinely used in clinical microbiology to liquefy respiratory specimens, but it has also been proven effective to detach biofilm from orthopaedic prosthesis (Drago et al. 2012, 2013). Since it is crucial to discriminate implant-related infections from aseptic loosening in orthopaedics, and because of the difficulty to diagnose subclinical infections, a prompt diagnosis of indwelling device-related infection is important for successful treatments (Borens et al. 2013). A fast microbiological diagnosis and bacterial identification should be recommended in order to set up a specific antimicrobial therapy. According to this strategy, the bacterial detachment from biofilm on explants should be accelerated by supporting the pathogen viability.

Technology Process of (2S,3S)-1,4-Dimercaptobutane-2,3-diol

There total 5 articles about (2S,3S)-1,4-Dimercaptobutane-2,3-diol 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,N-dimethyl-formamide (68-12-2,33513-42-7) + diothiothreitol (3483-12-3,6892-68-8,7634-42-6,16096-97-2,27565-41-9,35454-97-8)

Guidance literature:

Reference yield:

trans-4,5-dihydroxy-1,2-dithiane → diothiothreitol (3483-12-3,6892-68-8,7634-42-6,16096-97-2,27565-41-9,35454-97-8)

Guidance literature:

With C₁₂₀H₁₃₂N₁₂Ru₂S₂⁽⁴⁺⁾*4F₆P^(1-); triethylamine; In acetonitrile; at 22 ℃; Reagent/catalyst; Catalytic behavior; Irradiation;

DOI:10.1002/chem.201804037

Reference yield:

→ diothiothreitol (3483-12-3,6892-68-8,7634-42-6,16096-97-2,27565-41-9,35454-97-8)

Guidance literature:

DOI:10.1021/jo00422a034

upstream raw materials:

cis-4,5-dihydroxy-1,2-dithiane

trans-1,2-dithiane-4,5-diol

Downstream raw materials:

(2-{(2S,3S)-2,3-Dihydroxy-4-[2-(4-methoxy-benzyloxycarbonylamino)-ethyldisulfanyl]-butyldisulfanyl}-ethyl)-carbamic acid 4-methoxy-benzyl ester

C₄H₈O₂S₂^(1-)

Refernces

Effect of the carbamoyl group attached to an axial ligand portion of a novel bleomycin model on a dioxygen activating reaction

10.1248/cpb.46.1635

This research investigates the effect of a carbamoyl group attached to an axial ligand portion of a novel bleomycin (BLM) model compound on its redox reaction and oxygen activating ability. The study aims to clarify the role of the carbamoyl group in the redox cycle of the Fe-BLM complex. The key chemicals used include a novel BLM model compound (II) with a diaminopropionamide (DAPA) moiety as the axial ligand and a lauryl group as the steric factor, iron(II) sulfate for forming the Fe complex, dioxygen for the redox reaction, and dithiothreitol (DTT) as a reducing agent. The researchers synthesized the model compound II and conducted kinetic studies using UV-Vis spectroscopy and EPR methods. They found that the presence of the carbamoyl group on the DAPA portion significantly enhances the oxygen activating ability of the Fe(II) complex and facilitates the reduction process of the resulting Fe(III) complex, indicating that the carbamoyl group plays a crucial role in accelerating the redox cycle and improving the oxygen activation efficiency of the Fe-BLM complex.