Merck
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803200

Sigma-Aldrich

DTSSP (3,3′-dithiobis(sulfosuccinimidyl propionate))

Empirical Formula (Hill Notation):
C14H14N2O14S4Na2
Molecular Weight:
608.51
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥80%

form

powder

mol wt

608.51

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

soluble (>6mg/ml in water)

shipped in

ambient

storage temp.

2-8°C

SMILES string

O=C(CC1S(=O)([O-])=O)N(OC(CCSSCCC(ON2C(CC(S(=O)([O-])=O)C2=O)=O)=O)=O)C1=O.[Na+].[Na+]

InChI

1S/C14H16N2O14S4.2Na/c17-9-5-7(33(23,24)25)13(21)15(9)29-11(19)1-3-31-32-4-2-12(20)30-16-10(18)6-8(14(16)22)34(26,27)28;;/h7-8H,1-6H2,(H,23,24,25)(H,26,27,28);;/q;2*+1/p-2

InChI key

XRWWBWZHHSXBNC-UHFFFAOYSA-L

Related Categories

General description

DTSSP is 3,3′-Dithiobis(sulfosuccinimidylpropionate), which contains an amine-reactive N-hydroxysulfosuccinimide (sulfo-NHS) ester at each end of an 8-carbon spacer arm. Sulfo-NHS esters react with primary amines at pH 7-9 to form stable amide bonds, along with release of the N-hydroxysulfosuccinimide leaving group. Proteins, including antibodies, generally have several primary amines in the side chain of lysine (K) residues and the N-terminus of each polypeptide that are available as targets for sulfo-NHS-ester crosslinking reagents. DSS, the non-sulfonated analog of DTSSP is also available for applications that require a membrane-permeable crosslinker.

Features and Benefits

  • Reactive groups: sulfo-NHS ester (both ends)
  • Reactive towards: amino groups (primary amines)
  • Sulfo-NHS ester reacts rapidly with any primary amine-containing molecule
  • Disulfide bond in the spacer arm is readily cleaved by 10-50 mM DTT or TCEP at pH 8.5
  • Spacer arm also easily cleaved with reducing SDS-PAGE sample loading
  • Cleavable crosslinker allows separation of crosslinked products
  • Water-soluble; compare with DSP
  • Membrane-impermeable, allowing for cell surface labeling

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.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

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Certificate of Origin

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