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A9043

Sigma-Aldrich

S-Acetylthioglycolic acid N-hydroxysuccinimide ester

≥95% (TLC), powder

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C8H9NO5S
Číslo CAS:
76931-93-6
Molekulová hmotnost:
231.23
Beilstein/REAXYS Number:
7815491
MDL number:
MFCD00036891
UNSPSC Code:
12352100
PubChem Substance ID:
24891221
NACRES:
NA.22

Quality Level

200

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Osvědčení o analýze (COA)

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M H Vingerhoeds et al.
Pharmaceutical research, 13(4), 604-610 (1996-04-01)
Immuno-enzymosomes are tumor-specific immunoliposomes bearing enzymes on their surface. These enzymes are capable of converting relatively nontoxic prodrugs into active cytostatic agents. The enzyme beta-glucuronidase (GUS)4 was coupled to the external surface of immunoliposomes directed against ovarian carcinoma cells. This
Yi Wang et al.
Nature protocols, 2(4), 972-978 (2007-04-21)
The mercaptoacetyltriglycine (MAG3) chelator has been shown to stably complex technetium-99m (99mTc) for nuclear imaging and radiorhenium (186/188Re) for tumor radiation therapy studies. The bifunctional N-hydroxysuccinimidyl ester of MAG3 with S-acetyl protection (N-hydroxysuccinimidyl S-acetylmercaptoacetyltriglycinate (NHS-MAG3)) has been successfully used to
R A Schwendener et al.
Biochimica et biophysica acta, 1026(1), 69-79 (1990-07-09)
The two coupling agents SPDP (N-succinimidyl-3-(2-pyridyldithio)propionate) and SATA (N-succinimidyl-S-acetylthioacetate) were compared in their efficiency and feasibility to couple monoclonal antibodies (Abs) via thioether linkage to liposomes functionalized by various lipophilic maleimide compounds like N-(3-maleimidopropionyl)-N2-palmitoyl-L-lysine methyl ester (MP-PL), N-(3-maleimidopropionyl)phosphatidylethanolamide (MP-PE), N6-(6-maleimidocaproyl)-N2-palmitoyl-L-lysine
Jing-Tang Lin et al.
PloS one, 7(4), e36086-e36086 (2012-05-09)
To develop a fluorescent ruthenium complex for biosensing, we synthesized a novel sulfhydryl-reactive compound, 4-bromophenanthroline bis-2,2'-dipyridine Ruthenium bis (hexafluorophosphate). The synthesized Ru(II) complex was crosslinked with thiol-modified protein G to form a universal reagent for fluorescent immunoassays. The resulting Ru(II)-protein
R G Melton et al.
Journal of immunological methods, 158(1), 49-56 (1993-01-14)
Conjugates of F(ab')2 fragment of the monoclonal antibody A5B7 coupled to carboxypeptidase G2 (CPG2) have been produced using the heterobifunctional reagents 2-mercapto-[S-acetyl]acetic acid, N-hydroxysuccinimide ester (SATA) and m-maleimidobenzoyl-N-hydroxysuccinimide ester (SMPB). The effect of various levels of modifying reagent on enzyme
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