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D3669

Sigma-Aldrich

3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester)

powder

Synonym(s):

DTSP, Di(N-succinimidyl) 3,3′-dithiodipropionate, Dithiobis(succinimidyl propionate), Lomant’s reagent

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About This Item

Empirical Formula (Hill Notation):
C14H16N2O8S2
CAS Number:
57757-57-0
Molecular Weight:
404.42
Beilstein:
1518074
EC Number:
260-931-5
MDL number:
MFCD00042045
UNSPSC Code:
12352106
PubChem Substance ID:
24893777
NACRES:
NC.07

form

powder

reaction suitability

reagent type: cross-linking reagent

solubility

chloroform: 50 mg/mL
DMF: soluble
acetone: soluble

storage temp.

−20°C

SMILES string

O=C(CCSSCCC(=O)ON1C(=O)CCC1=O)ON2C(=O)CCC2=O

InChI

1S/C14H16N2O8S2/c17-9-1-2-10(18)15(9)23-13(21)5-7-25-26-8-6-14(22)24-16-11(19)3-4-12(16)20/h1-8H2

InChI key

FXYPGCIGRDZWNR-UHFFFAOYSA-N

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General description

3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester) (DSP) is a homobifunctional cross-linking reagent containing a cleavable disulfide linkage. It is typically coupled to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5).

Application

3,3′-Dithiodipropionic acid di(N-hydroxysuccinimide ester) (DSP) has been used as a protein cross-linker.

Features and Benefits

The disulfide linkage is cleavable by mild reduction.

Caution

Avoid use of reducing agents during coupling reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M Darder et al.
Analytical chemistry, 71(24), 5530-5537 (2000-01-07)
Exposure of gold surfaces to solutions of dithiobis N-succinimidyl propionate (DTSP) gives rise to the modification of the surface with N-succinimidyl-3-thiopropionate (NSTP) which can, in turn, react with amino groups allowing for the covalent immobilization of enzymes such as horseradish
Protein phosphatases 2C regulate the activation of the Snf1-related kinase OST1 by abscisic acid in Arabidopsis.
Vlad F
Plant Cell, 21, 3170-3170 (2009)
Lin Liu et al.
The Analyst, 137(16), 3794-3799 (2012-07-06)
In this paper, we report a simple, sensitive and selective colorimetric visualization of dopamine (DA) using dithiobis(succinimidylpropionate) (DSP)-modified gold nanoparticles (AuNPs) as probes and ferric ions as cross-linkers. Via the standard amine coupling reaction between the amino groups of DA
Suzanne Durocher et al.
Journal of the American Chemical Society, 131(7), 2475-2477 (2009-01-31)
Disulfide-linked gold nanoparticles (AuNP) were synthesized by reacting dithiobis[succinimidylpropionate] (DSP) coated nanoparticles with glutathione disulfide. AuNP-cross-linking was monitored by the red shift and broadening of the AuNP's localized surface plasmon absorption resonance (LSPR) spectrum. The exposure of the disulfide-linked AuNPs
Sunil K Arya et al.
The Analyst, 135(8), 1941-1946 (2010-07-01)
This paper reports on an ultrasensitive, disposable, impedimetric biosensor for cortisol detection. C-Mab (a Cortisol specific monoclonal antibody) was covalently immobilized via amide bond on the surface of the interdigitated micro-electrodes (IDmicroEs) functionalized with dithiobis(succinimidyl propionate) (DTSP) self-assembled monolayer (SAM).
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