2,5-dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetate

• ChemBase ID: 155124
• Molecular Formular: C8H9NO5S
• Molecular Mass: 231.22576
• Monoisotopic Mass: 231.02014339
• SMILES: CC(=O)SCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CSC(=O)C
• InChI: InChI=1S/C8H9NO5S/c1-5(10)15-4-8(13)14-9-6(11)2-3-7(9)12/h2-4H2,1H3
• InChIKey: FLCQLSRLQIPNLM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 2-(acetylsulfanyl)acetate
• Synonyms: N-Succinimidyl (acetylthio)acetate; N-Succinimidyl S-acetylthioglycolate; S-Acetylthioglycolic acid NHS ester; S-Acetylthioglycolic acid N-hydroxysuccinimide ester; Ethanethioic Acid S-[2-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl] Ester; SATA; N-Succinimidyl-S-acetylthioacetate; N-丁二酸S-乙酰基巯基乙二醇酯; N-琥珀酰亚胺基-S-乙酰硫基乙酸酯; S-乙酰硫基乙酸琥珀酰亚胺酯; N-琥珀酰亚胺基-S-乙酰硫基乙酸酯

Database IDs

• CAS Number: 76931-93-6
• MDL Number: MFCD00036891
• Beilstein Number: 7815491
• PubChem SID: 162249262; 24891221; 24845178
• PubChem CID: 127532

CALCULATED PROPERTIES

• Acid pKa: 17.706568
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.78658736
• LogD (pH = 7.4): -0.78658736
• Log P: -0.78658736
• Molar Refractivity: 50.4945 cm^3
• Polarizability: 20.194914 Å^3
• Polar Surface Area: 80.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble50 mg/mL; Chloroform; DMF: soluble; Ethyl Acetate
• Apperance: powder; White to Off-White Solid
• Melting Point: 90-95 °C; 98-100°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (TLC); ≥95.0% (CHN)
• Grade: purum
• Empirical Formula (Hill Notation): C8H9NO5S

DETAILS

Sigma Aldrich - A9043

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.

Sigma Aldrich - 01482

General description
cross-linking reagent
Other Notes
Modification (thionylation) of proteins1

Toronto Research Chemicals - S690010

Reacts with primary amines to add protected sulfhydryls.

REFERENCES

• Duncan, R.J.S., et al.: Anal. Biochem., 132, 68 (1983)