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A9043

S-Acetylthioglycolic acid N-hydroxysuccinimide ester

Name: S-Acetylthioglycolic acid N-hydroxysuccinimide ester
Brand: SIGMA

≥95% (TLC), powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):

C₈H₉NO₅S

Número de CAS:

76931-93-6

Peso molecular:

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)

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A sulfhydryl-reactive ruthenium (II) complex and its conjugation to protein G as a universal reagent for fluorescent immunoassays.

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

Comparative studies of the preparation of immunoliposomes with the use of two bifunctional coupling agents and investigation of in vitro immunoliposome-target cell binding by cytofluorometry and electron microscopy.

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

Delivery of antiviral agents in liposomes.

Nejat Düzgüneş et al.

Methods in enzymology, 391, 351-373 (2005-02-22)

The intracellular activity of certain antiviral agents, including antisense oligonucleotides, acyclic nucleoside phosphonates, and protease inhibitors, is enhanced when they are delivered in liposome-encapsulated form. In this chapter we describe the preparation of pH-sensitive liposomes encapsulating antisense oligonucleotides, ribozymes, and

Use of antibody as carrier of oligomers of peptidomimetic alphavbeta3 antagonist to target tumor-induced neovasculature.

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

Conjugation of methacrylamide groups to a model protein via a reducible linker for immobilization and subsequent triggered release from hydrogels.

Ellen Verheyen et al.

Macromolecular bioscience, 10(12), 1517-1526 (2010-09-09)

An efficient strategy is reported to introduce methacrylamide groups on the lysine residues of a model protein (lysozyme) for immobilization and triggered release from a hydrogel network. A novel spacer unit was designed, containing a disulfide bond, such that the

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