197327
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:
Molecular Weight:
174.17
NACRES:
NA.23
PubChem Substance ID:
UNSPSC Code:
12162002
EC Number:
230-135-2
MDL number:
InChI key
AHTFMWCHTGEJHA-UHFFFAOYSA-N
InChI
1S/C6H6O4S/c1-3(7)11-4-2-5(8)10-6(4)9/h4H,2H2,1H3
SMILES string
CC(=O)SC1CC(=O)OC1=O
assay
96%
mp
83-86 °C (lit.)
storage temp.
2-8°C
Quality Level
Related Categories
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.
signalword
Warning
hcodes
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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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
Hermanson GT et al.
Bioconjugate Techniques null
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
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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