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Merck
CN

D3669

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
UNSPSC Code:
12352106
NACRES:
NC.07
PubChem Substance ID:
24893777
EC Number:
260-931-5
Beilstein/REAXYS Number:
1518074
MDL number:
MFCD00042045
Form:
powder

Key Documents

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InChI key

FXYPGCIGRDZWNR-UHFFFAOYSA-N

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

SMILES string

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

form

powder

reaction suitability

reagent type: cross-linking reagent

solubility

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

storage temp.

−20°C

Quality Level

200

Related Categories

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.

Disclaimer

Avoid use of reducing agents during coupling reactions.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB9894
BCBS4530V
BCBT0589
BCBS9845V
BCBT0455

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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)
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
M Gamero et al.
Biosensors & bioelectronics, 25(9), 2038-2044 (2010-02-23)
The design and characterization of a lactate biosensor using a nanostructured rough gold surface as a transducer is reported. The biosensor is developed by immobilization of lactate oxidase (LOx), on a rough gold electrode modified with a self-assembled monolayer of
Rui Deng et al.
Journal of controlled release : official journal of the Controlled Release Society, 140(1), 40-46 (2009-07-25)
The commercially available branched polyethyleneimine (PEI) with a molar mass of 25 kD (PEI-25K) is an effective in vitro vector to transfer genes, but its cytotoxicity limits its applications in bio-related research. To solve such an efficiency-versus-cytotoxicity catch-22 problem, the
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