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A9043

Sigma-Aldrich

S-Acetylthioglycolic acid N-hydroxysuccinimide ester

≥95% (TLC), powder

Synonym(s):

N-Succinimidyl (acetylthio)acetate, N-Succinimidyl S-acetylthioglycolate, S-Acetylthioglycolic acid NHS ester, SATA

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About This Item

Empirical Formula (Hill Notation):
C8H9NO5S
CAS Number:
Molecular Weight:
231.23
Beilstein:
7815491
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

Assay

≥95% (TLC)

form

powder

solubility

acetonitrile: 50 mg/mL
DMF: soluble

storage temp.

−20°C

SMILES string

CC(=O)SCC(=O)ON1C(=O)CCC1=O

InChI

1S/C8H9NO5S/c1-5(10)15-4-8(13)14-9-6(11)2-3-7(9)12/h2-4H2,1H3

InChI key

FLCQLSRLQIPNLM-UHFFFAOYSA-N

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Application

Thiolating reagent for primary amines; thiol can be deprotected under mild conditions. Typically, couples initially to a molecule containing primary amine by amide bond buffered at pH 7.5. Deprotection may be accomplished with 0.05 M hydroxylamine at neutral pH. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.

Other Notes

Note that the ester couples very efficiently to primary amines compared to other thiolating reagents. In addition, this reagent will neutralize original amine positive charge.

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

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Screening of monoclonal antibodies using antigens labeled with acetylcholinesterase.
Y Frobert et al.
Methods in molecular biology (Clifton, N.J.), 80, 57-68 (1998-07-17)
Magnus Bergkvist et al.
Methods in molecular biology (Clifton, N.J.), 751, 381-400 (2011-06-16)
Over the last decade, scanning probe microscopy (SPM) techniques, such as atomic force microscopy (AFM), have played an important role in a variety of biophysical research efforts. This straightforward technique has the capability to measure forces down to a few
Malcolm N Jones
Methods in enzymology, 391, 211-228 (2005-02-22)
Methods are described for the preparation of anionic and cationic liposomes and proteoliposomes with covalently linked lectins or antibodies by the extrusion technique (vesicles by extrusion, VETs). The liposomes are prepared from the phospholipid dipalmitoylphosphatidylcholine (DPPC), together with the anionic
In Soo Shin et al.
Bioconjugate chemistry, 18(3), 821-828 (2007-03-23)
Sulfhydryl selective reactions were explored to conjugate oligomers of a peptidomimetic integrin alphavbeta3 antagonist, 4-[2-(3,4,5,6-tetrahydropyrimidine-2-ylamino)ethyloxy]benzoyl-2-(S)-aminoethylsulfonylamino-beta-alanine (IA) to monoclonal antibody (MoAb) to increase integrin alphavbeta3 receptor-binding avidity. To generate sulfhydryl groups, N-succinimidyl-S-acetylthioacetate (SATA) was conjugated to both MoAb and IA. Sulfhydryl
N S Postma et al.
Antimicrobial agents and chemotherapy, 43(5), 1027-1033 (1999-05-01)
The introduction of reactive thiol groups in recombinant human tumor necrosis factor (TNF) alpha (rhTNF-alpha) by the reagent succinimidyl-S-acetylthioacetate resulted in the formation of a chemically stabilized rhTNF-alpha trimer (rhTNFalpha-AT; as determined by sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis). rhTNFalpha-AT

Questions

  1. Hello, Could you tell me the percentage of impurities and define specifically which impurities we can find in this reagent ? Thank you,

    1 answer
    1. The product impurities are not identified or quantified. Please see the product specification sheet:
      https://www.sigmaaldrich.com/specification-sheets/457/256/A9043-BULK________SIGMA____.pdf.

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