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Merck
CN

A1251

Sigma-Aldrich

S-Acetylmercaptosuccinic anhydride

≥98%

Synonym(s):

2-(Acetylthio)succinic anhydride, SAMSA

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About This Item

Empirical Formula (Hill Notation):
C6H6O4S
CAS Number:
Molecular Weight:
174.17
EC Number:
MDL number:
UNSPSC Code:
12162002
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Assay

≥98%

form

powder

mp

83-86 °C (lit.)

solubility

acetone: 100 mg/mL
DMF: soluble

storage temp.

−20°C

SMILES string

CC(=O)SC1CC(=O)OC1=O

InChI

1S/C6H6O4S/c1-3(7)11-4-2-5(8)10-6(4)9/h4H,2H2,1H3

InChI key

AHTFMWCHTGEJHA-UHFFFAOYSA-N

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Application

Thiolating reagent for primary amines; thiol can be deprotected under mild conditions. Typically, coupled initially to molecule containing primary amine by amide bond buffered at pH 7.5. Deprotection may be accomplished with .05 M hydroxylamine at neutral pH. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.

Other Notes

Note that the anydride is very reactive and less stable in aqeuous buffer than ester derivative. In addition, this reagent will replace positive amine charge with negative carboxyl.

Regulatory Information

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Introduction of sulfhydryl groups into proteins using acetylmercaptosuccinic anhydride.
I M KLOTZ et al.
Archives of biochemistry and biophysics, 96, 605-612 (1962-03-01)
E S Rector et al.
Journal of immunological methods, 24(3-4), 321-336 (1978-01-01)
A novel procedure for the synthesis of well-defined protein-protein conjugates is described using ovalbumin (OA) and IgG as test proteins. This procedure involves the highly selective and rapid reaction of alkyl halide and sulfhydryl groups, which have been grafted, respectively

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