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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

Quality Level

200

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)

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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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)
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
N S Green et al.
Protein science : a publication of the Protein Society, 10(7), 1293-1304 (2001-06-23)
Homobifunctional chemical cross-linking reagents are important tools for functional and structural characterization of proteins. Accurate measures of the lengths of these molecules currently are not available, despite their widespread use. Stochastic dynamics calculations now provide quantitative measures of the lengths
Michael Neu et al.
Biomacromolecules, 7(12), 3428-3438 (2006-12-13)
Stabilized PEI/DNA polyplexes were generated by cross-linking PEI with biodegradable disulfide bonds. The reaction conversion of different PEIs with the amine reactive cross-linker dithiobis(succinimidyl propionate) (DSP) was investigated, and the molecular weight of the reaction products was identified. Light scattering
Antonio N Calabrese et al.
Rapid communications in mass spectrometry : RCM, 27(1), 238-248 (2012-12-15)
It has been shown that the disulfide moiety in the chemical cross-linking reagent dithiobis(succinimidyl)propionate (DSP), which is similar in structure to the natural cystine disulfide, cleaves preferentially to the peptide backbone in the negative ion mode. However, the tandem mass
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