Dithiothreitol

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Structural formula
Structure of dithiothreitolFischer projection of dithiothreitol
General
Surname Dithiothreitol, DTT
other names
  • Cleland's reagent
  • 1,4-dimercapto-2,3-butanediol
  • Butane-2,3-diol-1,4-dithiol
Molecular formula C 4 H 10 O 2 S 2
Brief description

white solid with an unpleasant odor

External identifiers / databases
CAS number
  • 3483-12-3 (DL- threo )
  • 27565-41-9 (DL - (+ -) - threo -form)
  • 16096-97-2 (L- threo )
  • 7634-42-6 (unspecified)
EC number 222-468-7
ECHA InfoCard 100.020.427
PubChem 446094
DrugBank DB04447
Wikidata Q414783
properties
Molar mass 154.25 g mol −1
Physical state

firmly

Melting point
  • 40–43 ° C ( DL - threo )
  • 50–52 ° C ( L - threo )
  • 82–83 ° C ( erythro )
solubility

very good in water (1500 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dithiothreitol (DTT) is a chemical compound also called Cleland's reagent . It is formally derived from the sugar alcohol Threit or Threitol, which belongs to the structural type of threose . It occurs in two stereoisomers : the (2 S , 3 S ) -form ( 1 ) is derived from the D- threose, the (2 R , 3 R ) -form ( 2 ) from the L- threose.

DTT is used in protein biochemistry . It preserves proteins in the cell interior in their functional form by preventing the oxidation of sulfhydryl groups (SH-) to disulfide bridges by atmospheric oxygen . On the other hand, it can destroy the folding of proteins , the structure of which is stabilized by disulfide bridges, by reducing them. It is an important reagent in the sample buffer for SDS-PAGE and Western blotting .

The oxidation leads to the formation of an intramolecular disulfide bridge, which forms a six-membered ring. Thereby the oxidized form is energetically favored.

See also

Individual evidence

  1. ↑ a b c d e f g Entry on 1,4-Dimercapto-2,3-butanediol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .