2,5-dioxopyrrolidin-1-yl 4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylate

• ChemBase ID: 104274
• Molecular Formular: C16H18N2O6
• Molecular Mass: 334.32392
• Monoisotopic Mass: 334.11648631
• SMILES: O=C1CCC(=O)N1OC(=O)C1CCC(CC1)CN1C(=O)C=CC1=O
• Canonical SMILES: O=C(C1CCC(CC1)CN1C(=O)C=CC1=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2
• InChIKey: JJAHTWIKCUJRDK-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)methyl]cyclohexane-1-carboxylate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexane-1-carboxylate; SMCC
• Synonyms: 4-(Maleimidomethyl)cyclohexane-1-carboxylic acid N-hydroxysuccinimide ester; N-Succinimidyl 4-(maleimidomethyl)cyclohexanecarboxylate; Succinimidyl 4-[N-maleimidomethyl]-cyclohexane-1-carboxylate; 4-(N-MALEIMIDOMETHYL)-CYCLOHEXANE-1-CARBOXYLIC ACID N-HYDROXYSUCCINIMIDE ESTER; SMCC; 4-(N-Maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester; 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate; 4-(N-Maleimidomethyl)cyclohexane-1-carboxylic Acid N-Hydroxysuccinimide Ester; NSC 344483; N-Succinimidyl 4-(Maleimidomethyl)cyclohexane-1-carboxylate; N-琥珀酰亚胺基4-(马来酰亚胺基甲基)环己烷羧酸酯; 4-(N-马来酰亚胺基甲基)环己烷-1-羧酸琥珀酰亚胺酯

Database IDs

• CAS Number: 64987-85-5
• MDL Number: MFCD00009634
• Beilstein Number: 1555271
• PubChem SID: 24897020; 24882450; 162091875
• PubChem CID: 125175

CALCULATED PROPERTIES

• Acid pKa: 17.70829
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.2943863
• LogD (pH = 7.4): 0.2943863
• Log P: 0.2943863
• Molar Refractivity: 80.7868 cm^3
• Polarizability: 31.288792 Å^3
• Polar Surface Area: 101.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble50 mg/mL; Dichloromethane; DMF: soluble; Ethyl Acetate
• Apperance: powder; White Crystalline Solid
• Melting Point: 175-180 °C; 179°C; 180-182 °C(lit.); 180-182°C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C, Desiccate
• Storage Warning: Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~95% (HPLC); ≥98%; 98%; 98+%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C16H18N2O6

DETAILS

MP Biomedicals - 02155309

(Succinimidyl 4-[N-maleimidomethyl]-cyclohexane-1-carboxylate) Crystalline

Sigma Aldrich - M5525

Application
A heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. Typically coupled initially to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). The second coupling is 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. Contains 9 atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.

Sigma Aldrich - 63181

Other Notes
Derivatization of monoclonal antibodies with SMCC and conjugation with oligonucleotide for 2-step radioimmunotherapy1

Toronto Research Chemicals - S690400

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. It conjugates anti-digoxin F(ab')2 fragments to Δ-galactosidase. Conjugates hIgG to alkaline phosphatase.Spacer Arm: 11.6 Angstroms

REFERENCES

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• Maham, D.G., et al.: Anal. Biochem., 162, 163 (1987)
• Yoshitake, S., et al.: Eur. J. Biochem., 101, 395 (1987)
• Freytag, J.W., et al.: Clin. Chem., 30(1987)
• 1494 (1987)
• Mahan, D.E., et al.: Anal. Biochem., 162, 163 (1987)
• Peeters, J.M., et al.: J. Immunol