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774405

Sigma-Aldrich

(S)-2-Aminobutane-1,4-dithiol hydrochloride

99% (titration)

Synonym(s):

(S)-2-Aminobutane-1,4-dithiol hydrochloride, (2S)-2-Amino-1,4-dimercaptobutane hydrochloride, DTBA, Dithiobutylamine

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About This Item

Empirical Formula (Hill Notation):
C4H11NS2 · HCl
CAS Number:
1363376-98-0
Molecular Weight:
173.73
MDL number:
MFCD23704430
UNSPSC Code:
12352200
PubChem Substance ID:
329767683
NACRES:
NA.22

Assay

99% (titration)

form

solid

reaction suitability

reagent type: reductant

mp

210-225 °C

storage temp.

2-8°C

SMILES string

Cl.N[C@H](CS)CCS

InChI

1S/C4H11NS2.ClH/c5-4(3-7)1-2-6;/h4,6-7H,1-3,5H2;1H/t4-;/m0./s1

InChI key

HWWPXJZINVJNBM-WCCKRBBISA-N

Application

(S)-2-Aminobutane-1,4-dithiol hydrochloride (DTBA), also known as dithiobutylamine, is a biological reducing reagent with enhanced properties over other commonly used reagents. DTBA was shown to reduce small molecule disulfides 3-5x faster than DTT and was able to reduce (activate) the cysteine dependent protease papain 14x faster than DTT. In addition, due to the presence of the primary amine group, removal of DTBA from mixtures after use is simplified and can be achieved using cation exchange resin.
Dithiobutylamine or DTBA is a new biological reducing reagent with enhanced properties over other commonly used reagents. DTBA was shown to reduce small molecule disulfides 3-5x faster than DTT and was able to reduce (activate) the cysteine dependent protease papain 14x faster than DTT. In addition, due to the presence of the primary amine group, removal of DTBA from mixtures after use is simplified and can be achieved using cation exchange resin.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Coordination properties of dithiobutylamine (DTBA), a newly introduced protein disulfide reducing agent.
Adamczyk J, et al.
Inorganic Chemistry, 54(2), 596-606 (2014)
Javier Troyano et al.
Inorganic chemistry, 58(5), 3290-3301 (2019-02-13)
Direct reactions under ambient conditions between CuX (X = Br, I) and thiobenzamide (TBA) were carried out at different ratios, giving rise to the formation of a series of one-dimensional (1D) coordination polymers, (CPs) [CuI(TBA)] n (1), [Cu3I3(TBA)2] n (4)
Mozhdeh Imaninezhad et al.
Bioconjugate chemistry, 30(1), 34-46 (2018-12-19)
Macroporous cell-laden hydrogels have recently gained recognition for a wide range of biomedical and bioengineering applications. There are various approaches to create porosity in hydrogels, including lyophilization or foam formation. However, many do not allow a precise control over pore
A potent, versatile disulfide-reducing agent from aspartic acid.
Lukesh III, et al.
Journal of the American Chemical Society, 134(9), 4057-4059 (2012)
Sean B Johnston et al.
PloS one, 10(1), e0116898-e0116898 (2015-01-22)
Phosphatase and tensin homologue deleted from chromosome ten (PTEN) is a lipid phosphatase tumor suppressor that is lost or inactivated in most human tumors. The enzyme catalyzes the hydrolysis of phosphatidylinositol-(3,4,5)-trisphosphate (PIP3) to form phosphatidylinositol-(4,5)-bisphosphate (PIP2) and inorganic phosphate. Here
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Raines Group – Professor Product Portal

Professor Ron Raines works with Sigma-Aldrich on the development of reagents and tools for chemical biology such as the traceless Staudinger ligation reagent (670359). DTBA (774405), a superior biological reducing reagent to DTT, is another technology to come out of the Raines lab.

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