2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoate

• ChemBase ID: 102945
• Molecular Formular: C12H12N2O6
• Molecular Mass: 280.23348
• Monoisotopic Mass: 280.06953611
• SMILES: O=C(CCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCCN1C(=O)C=CC1=O
• InChI: InChI=1S/C12H12N2O6/c15-8-3-4-9(16)13(8)7-1-2-12(19)20-14-10(17)5-6-11(14)18/h3-4H,1-2,5-7H2
• InChIKey: PVGATNRYUYNBHO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxopyrrol-1-yl)butanoate
• Synonyms: 1-[4-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-4-oxobutyl]-1H-pyrrole-2,5-dione; 4-Maleimidobutyric Acid N-Hydroxysuccimide Ester; N-(4-Maleimidebutyryloxy)succinimide; 4-Maleimidobutyric Acid N-Succinimidyl Ester; N-(γ-Maleimidobutyryloxy)succinimide; N-Succinimidyl 4-maleimidobutyrate; 4-Maleimidobutyric acid N-hydroxysuccinimide ester; 2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoate; GMBS; N-Succinimidyl-4-maleimidobutyrate; 4-Maleimidobutyric acid N-hydroxysuccinimide ester; 4-Maleimidobutyric acid N-succinimidyl ester; N-(γ-MALEIMIDOBUTYRYL-OXY)SUCCINIMIDE

Database IDs

• CAS Number: 80307-12-6
• MDL Number: MFCD00036817
• Beilstein Number: 6427689
• PubChem SID: 162089357; 24882441
• PubChem CID: 133440

CALCULATED PROPERTIES

• Acid pKa: 17.709116
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.0389842
• LogD (pH = 7.4): -1.0389842
• Log P: -1.0389842
• Molar Refractivity: 64.3409 cm^3
• Polarizability: 24.729916 Å^3
• Polar Surface Area: 101.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 123-129 °C; 126-129°C; 130-132°C
• Hydrophobicity(logP): -0.443

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere; 2-8°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC); 95%
• Empirical Formula (Hill Notation): C12H12N2O6

DETAILS

MP Biomedicals - 02150004

Heterobifunctional crosslinker useful for the preparation of stable defined conjugates for enzyme immunoassays.

Sigma Aldrich - 63175

Application
A heterobifunctional cross-linking reagent with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5). Second coupling specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Provides a 7-atom linker.

Toronto Research Chemicals - M136000

A short, sulfhydryl and amino reactive heterobifunctional crosslinking reagent. Introduces maleimide groups into IgM.

REFERENCES

• Kitagawa, T., et al., J. Biochem. , 94 : 1165, (1983).
• Keller, O., et al.: Helv. Chim. Acta., 58, 531 (1975)
• Fujiwara, K., et al.: J. Immunol. Meth., 112, 77 (1988)