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D9760

Sigma-Aldrich

L-(−)-Dithiothreitol

≥95% (titration)

Synonym(s):

(−)-Cleland’s Reagent, (2R,3R)-1,4-Dimercapto-2,3-butanediol, L-DTT, Cleland reagent chiral

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About This Item

Empirical Formula (Hill Notation):
C4H10O2S2
CAS Number:
16096-97-2
Molecular Weight:
154.25
Beilstein/REAXYS Number:
2036371
EC Number:
240-263-0
MDL number:
MFCD00064305
UNSPSC Code:
12352201
PubChem Substance ID:
24894326
NACRES:
NA.25

Quality Level

100

assay

≥95% (titration)

form

powder

color

white

mp

49 - 51 °C ((120 - 124 °F))

solubility

H2O: 50 mg/mL, clear to hazy, colorless

storage temp.

−20°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-/m0/s1

InChI key

VHJLVAABSRFDPM-IMJSIDKUSA-N

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Application

L-DTT [(2R,3R)-1,4-dimercapto-2,3-butanediol; L-dithiothreitol], a chiral bidentate dithiol with two stereogenic centers, may be used in chiroptical response research. L-DDT is proposed as a stereoselective reducing agent for disulfide bridges in complex molecules.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Chimia, 67(4), 236-239 (2013-08-24)
Chiral thiolate-protected gold clusters of atomic precision have gained increasing interest in recent years due to their potential use in catalysis, sensing or bioapplications. While the protection of gold clusters with chiral ligands is a rather trivial task, it was
Hermann Bultmann et al.
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Previous studies have shown that peptides containing the protein transduction domain (PTD) of the human immunodeficiency virus tat protein (GRKKRRQRRR) were effective inhibitors of herpes simplex virus type 1 (HSV-1) entry (H. Bultmann and C. R. Brandt, J. Biol. Chem.
Hiroshi Yao et al.
Langmuir : the ACS journal of surfaces and colloids, 29(21), 6444-6451 (2013-05-03)
We here present a study of cross-linking chemistry of optically inactive monothiol-protected gold clusters by chiral bidentate dithiol with two stereogenic centers, (2R,3R)-1,4-dimercapto-2,3-butanediol (L-dithiothreitol; L-DTT), and explore the impacts of the cross-linking on their chiroptical responses. The pristine protective ligand
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