1,4-dioxane 2,5-dioxopyrrolidin-1-yl 3-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}amino)propanoate

• ChemBase ID: 177928
• Molecular Formular: C16H21N3O10
• Molecular Mass: 415.35204
• Monoisotopic Mass: 415.12269389
• SMILES: C1CC(=O)N(C1=O)OC(=O)NCCC(=O)ON1C(=O)CCC1=O.O1CCOCC1
• Canonical SMILES: C1COCCO1.O=C(ON1C(=O)CCC1=O)CCNC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C12H13N3O8.C4H8O2/c16-7-1-2-8(17)14(7)22-11(20)5-6-13-12(21)23-15-9(18)3-4-10(15)19;1-2-6-4-3-5-1/h1-6H2,(H,13,21);1-4H2
• InChIKey: AQUFMAPQJCPCRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dioxane 2,5-dioxopyrrolidin-1-yl 3-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}amino)propanoate
• IUPAC Traditional name: dioxane 2,5-dioxopyrrolidin-1-yl 3-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}amino)propanoate
• Synonyms: N-[[N-[(Succinimidooxy)carbonyl]-β-alanyl]oxy]succinimide 1,4- Dioxane; N-Succinimidoxycarbonyl-β-alanine N-Succinimidyl Ester 1,4- Dioxane complex

Database IDs

• CAS Number: 1215667-16-5
• PubChem SID: 164233838
• PubChem CID: 45040423

CALCULATED PROPERTIES

• Acid pKa: 13.394622
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.8790483
• LogD (pH = 7.4): -1.8790487
• Log P: -1.8790483
• Molar Refractivity: 68.1087 cm^3
• Polarizability: 27.120058 Å^3
• Polar Surface Area: 139.39 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 163-164°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S689850

A short, amino reactive homobifunctional crosslinking reagent. Crosslinking distance 8.3 Å. It is useful in polymer coupling to proteins, because it may lead to a better selectivity among all the amino groups present in a protein, thus yielding less heterogeneous PEG-protein conjugates mixture because only the most nucleophilic and solvent exposed amines can react.

REFERENCES

• Gross, H., et al.: Tetrahedron, 24, 6935 (1968)
• Clark, R., et al.: J. Biol. Chem., 271, 21969 (1968)
• Guiotto, A., et al.: Bioorg. Med. Chem., 12, 5031 (1968)