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803618

Sigma-Aldrich

DTME (dithio-bis-maleimidoethane)

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Synonym(s):
1,1′-(dithiodi-2,1-ethanediyl)bis-1H-Pyrrole-2,5-dione, 1-[2-[[2-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethyl]dithio]ethyl]-1H-pyrrole-2,5-dione, DTME
Empirical Formula (Hill Notation):
C12H12N2S2O4
CAS Number:
71865-37-7
Molecular Weight:
312.36
MDL number:
MFCD01863385
UNSPSC Code:
12352200
PubChem Substance ID:
329768821
NACRES:
NA.22

Assay

≥90%

form

powder

mol wt

312.37

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

DMSO or DMF: soluble

shipped in

ambient

storage temp.

2-8°C

SMILES string

O=C(C=CC1=O)N1CCSSCCN2C(C=CC2=O)=O

InChI

1S/C12H12N2O4S2/c15-9-1-2-10(16)13(9)5-7-19-20-8-6-14-11(17)3-4-12(14)18/h1-4H,5-8H2

InChI key

SGVWDRVQIYUSRA-UHFFFAOYSA-N

General description

DTME is a homobifunctional, maleimide crosslinker for conjugation between sulfhydryl groups (-SH). Such bismaleimide crosslinkers are commonly used to explore and characterize protein structure (i.e., oligomerization) or protein interactions. DTME is similar in length to BMH but differs in containing a disulfide bond in its spacer arm, allowing crosslinks with DTME to be cleaved with reducing agent such as dithiothreitol (DTT).

Features and Benefits

  • Reactive groups: maleimide (both ends)
  • Reactive towards: sulfhydryl groups
  • Long (13.3A), cleavable, sulfhydryl-to-sulfhydryl crosslinker, composed of maleimide groups and 11-atom disulfide spacer arm
  • Water-insoluble—dissolve first in DMF or DMSO, then add to aqueous reaction buffers
  • Cleavable by reduction of disulfide spacer arm with DTT, TCEP or other reducing agent

Caution

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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