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Merck

43819

DL-Dithiothreitol

≥99.0% (RT)

Synonym(s):

threo-1,4-Dimercapto-2,3-butanediol, Cleland’s reagent, DTT

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About This Item

Linear Formula:
HSCH2CH(OH)CH(OH)CH2SH
CAS Number:
3483-12-3
Molecular Weight:
154.25
UNSPSC Code:
12352201
NACRES:
NA.21
PubChem Substance ID:
329756409
EC Number:
222-468-7
Beilstein/REAXYS Number:
1719757
MDL number:
MFCD00004877

Key Documents

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Quality Level

200

assay

≥99.0% (RT)

form

powder

reaction suitability

reagent type: reductant

impurities

≤0.3% 4,5-dihydroxy-1,2-dithiane

mp

40-43 °C, 41-44 °C (lit.)

solubility

acetone: freely soluble, H2O: 50 mg/mL, clear, colorless, H2O: freely soluble, chloroform: freely soluble, diethyl ether: freely soluble, ethanol: freely soluble, ethyl acetate: freely soluble

anion traces

sulfate (SO42-): ≤50 mg/kg

cation traces

Ca: ≤10 mg/kg, Cd: ≤5 mg/kg, Co: ≤5 mg/kg, Cr: ≤5 mg/kg, Cu: ≤5 mg/kg, Fe: ≤5 mg/kg, K: ≤50 mg/kg, Mg: ≤5 mg/kg, Mn: ≤5 mg/kg, Na: ≤250 mg/kg, Ni: ≤5 mg/kg, Pb: ≤5 mg/kg, Zn: ≤5 mg/kg

storage temp.

2-8°C

SMILES string

O[C@H](CS)[C@H](O)CS

InChI

1S/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m1/s1

InChI key

VHJLVAABSRFDPM-QWWZWVQMSA-N

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Application

An excellent reagent for maintaining SH groups in reduced state; quantitatively reduces disulfides. DTT is effective in sample buffers for reducing protein disulfide bonds prior to SDS-PAGE. DTT can also be used for reducing the disulfide bridge of the cross-linker N,N′-bis(acryloyl)cystamine to break apart the matrix of a polyacrylamide gel. DTT is less pungent and is less toxic than 2-mercaptoethanol. Typically, a seven fold lower concentration of DTT (100 mM) is needed than is used for 2-mercaptoethanol (5% v/v, 700 mM).
DL-Dithiothreitol is a pivotal component used in the preparation of buffer which in turn is utilized in the platelet cytosol preparation. It is also important in isolation of RNA by using guanidinium salts and homogenisation of tissue and cells.

Biochem/physiol Actions

DL-Dithiothreitol denatures proteins by reducing the disulphide bonds and reducing them to SH groups. It also prevents intramolecular and intermolecular disulfide bond formation between cysteine residues of proteins.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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John C Lukesh et al.
Journal of the American Chemical Society, 134(9), 4057-4059 (2012-02-23)
Dithiothreitol (DTT) is the standard reagent for reducing disulfide bonds between and within biological molecules. At neutral pH, however, >99% of DTT thiol groups are protonated and thus unreactive. Herein, we report on (2S)-2-amino-1,4-dimercaptobutane (dithiobutylamine or DTBA), a dithiol that
R G Knowles et al.
Proceedings of the National Academy of Sciences of the United States of America, 86(13), 5159-5162 (1989-07-01)
A soluble enzyme obtained from rat forebrain catalyzes the NADPH-dependent formation of nitric oxide (NO) and citrulline from L-arginine. The NO formed stimulates the soluble guanylate cyclase and this stimulation is abolished by low concentrations of hemoglobin. The synthesis of
M W Radomski et al.
Proceedings of the National Academy of Sciences of the United States of America, 87(13), 5193-5197 (1990-07-01)
Aggregation of human washed platelets with collagen is accompanied by a concentration-dependent increase in cyclic GMP but not cyclic AMP. NG-Monomethyl-L-arginine (L-MeArg), a selective inhibitor of nitric oxide (NO) synthesis from L-arginine, reduces this increase and enhances aggregation. L-Arginine, which
M B Donati et al.
Cancer research, 46(12 Pt 1), 6471-6474 (1986-12-01)
It has repeatedly been proposed that fibrin plays a role in tumor growth and metastasis. Among tumor cell products or activities which may promote clot formation, cancer procoagulant (CP), a direct activator of coagulation factor X, has been suggested to
Ananthakrishnan Soundaram Jeevarathinam et al.
Angewandte Chemie (International ed. in English) (2019-12-17)
We report a new approach to monitor drug release from nanocarriers via a paclitaxel-methylene blue conjugate (PTX-MB) with redox activity. This construct is in a photoacoustically silent reduced state inside poly(lactic-co-glycolic acid) (PLGA) nanoparticles (PTX-MB@PLGA NPs). During release, PTX-MB is
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