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Sigma-Aldrich

S-Acetylmercaptosuccinic anhydride

96%

Synonym(s):

2-(Acetylthio)succinic anhydride, SAMSA

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About This Item

Empirical Formula (Hill Notation):
C6H6O4S
CAS Number:
6953-60-2
Molecular Weight:
174.17
EC Number:
230-135-2
MDL number:
MFCD00005526
UNSPSC Code:
12162002
PubChem Substance ID:
24851822
NACRES:
NA.23

assay

96%

mp

83-86 °C (lit.)

storage temp.

2-8°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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General description

S-Acetylmercaptosuccinic anhydride is an amine reactive reagent, containing a sulfhydryl group. The anhydride region opens up, when attacked by an amine nucleophile, forming amine linkage. However, during this ring opening reaction, a free carboxylate group is formed rendering the molecule negatively charged. Activity to proteins and conformation of the molecule us affected by the charge reversal.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Introduction of sulfhydryl groups into proteins using acetylmercaptosuccinic anhydride
Klotz IM, et al.
Archives of Biochemistry and Biophysics, 96(3), 605-612 (1932)
L Greenfield et al.
Bioconjugate chemistry, 1(6), 400-410 (1990-11-01)
Ricin A chain immunotoxins disulfide cross-linked with conventional, sterically unhindered reagents have unsatisfactorily short circulating life times in vivo. (Acetylthio)succinic anhydride, a thiolating reagent with partial steric hindrance of the sulfur atom, does not remedy this situation. Sulfosuccinimidyl N-[3-(acetylthio)-3-methylbutyryl]-beta- alaninate
Monica A Serban et al.
Biomacromolecules, 8(9), 2821-2828 (2007-08-19)
Hyaluronan (HA) derivatives containing thiol-reactive electrophilic esters were prepared to react with thiol-modified macromolecules to give cross-linker-free hydrogels. Specifically, HA was converted to two haloacetate derivatives, HA bromoacetate (HABA) and HA iodoacetate (HAIA). In cytotoxicity assays, these reactive macromolecules predictably
Fabio Cannone et al.
The journal of physical chemistry. B, 110(33), 16491-16498 (2006-08-18)
A fluorescein derivative (SAMSA) bound to gold nanoparticles of different diameters is investigated by time-resolved fluorescence at the single molecule level in a wide dynamic range, from nanosecond to second time scale. The significant decrease of both SAMSA excited state
Travis A Cos et al.
Journal of clinical psychology in medical settings, 27(4), 704-715 (2019-09-15)
Peer recovery specialists (PRSs) combine their personal experiences with substance use and recovery with clinical skills to support patients in treatment for or recovery from substance use. This paper provides evaluation findings from a SAMHSA-funded program that integrated a PRS
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