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A9043

Sigma-Aldrich

S-Acetylthioglycolic acid N-hydroxysuccinimide ester

≥95% (TLC), powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C8H9NO5S
Numéro CAS:
76931-93-6
Poids moléculaire :
231.23
Numéro Beilstein :
7815491
Numéro MDL:
MFCD00036891
Code UNSPSC :
12352100
ID de substance PubChem :
24891221
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

≥95% (TLC)

Forme

powder

Solubilité

acetonitrile: 50 mg/mL
DMF: soluble

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Autres remarques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (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
Rükan Genç et al.
Analytical chemistry, 83(2), 563-570 (2010-12-16)
Liposomes are potential candidates as nanovesicles for the development of detection systems with improved sensitivity and detection limits, due to their capacity to encapsulate diverse types of signal enhancing molecules. An amperometric immunosensor exploiting enzyme encapsulating thermosensitive liposomes for the
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