2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

Base Information

• Chemical Name: 2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate
• CAS No.: 55750-63-5
• Molecular Formula: C14H16N2O6
• Molecular Weight: 308.291
• Hs Code.: 29280000
• European Community (EC) Number: 637-238-5
• UNII: AW858RP6BO
• DSSTox Substance ID: DTXSID40971129
• Nikkaji Number: J479.819H
• Wikidata: Q72509058
• Mol file: 55750-63-5.mol

Synonyms:N-(epsilon-maleimidocaproyloxy)succinimide;NMICOS

Chemical Property of 2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

Chemical Property:

• Appearance/Colour: White to cream colored crystals
• Vapor Pressure: 2.13E-09mmHg at 25°C
• Melting Point: 70-73 °C(lit.)
• Refractive Index: 1.577
• Boiling Point: 480.6 °C at 760 mmHg
• PKA: -2.21±0.20(Predicted)
• Flash Point: 244.5 °C
• PSA: 101.06000
• Density: 1.4 g/cm³
• LogP: -0.04520
• Storage Temp.: −20°C
• Sensitive.: Light & Moisture Sensitive & Hyg
• Solubility.: chloroform: 100mg/mL
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 308.10083623
• Heavy Atom Count: 22
• Complexity: 520

Purity/Quality:

98% ^*data from raw suppliers

6-Maleimidocaproic acid N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XnXi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-40
• Safety Statements: 26-36/37-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCN2C(=O)C=CC2=O
• Description: Mal-heptanoic NHS ester contains a maleimide group and an NHS ester. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.
• Uses: 6-Maleimidohexanoic acid N-hydroxysuccinimide ester can be used in:Synthesis of maleimide-activated carbohydrates for site-specific glycosylation of cysteine-containing peptides and proteins via maleimide-thiol ligation reaction.Synthesis of a glucuronide prodrug of doxorubicin bearing a maleimide side chain as an antitumor agent.Cross-linking oligonucleotides with the amino groups on the substrate to fabricate DNA microarrays.

Technology Process of 2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

There total 13 articles about 2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3) → 6-maleimidohexanoic acid N-hydroxylsuccinimide ester (55750-63-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

Reference yield: 90.0%

di(succinimido) carbonate (74124-79-1) + 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3) → 6-maleimidohexanoic acid N-hydroxylsuccinimide ester (55750-63-5)

Guidance literature:

With triethylamine; In dichloromethane; for 2h; Ambient temperature;

Reference yield: 85.0%

maleic anhydride (108-31-6) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 6-aminohexanoic acid (60-32-2,93208-38-9) → 6-maleimidohexanoic acid N-hydroxylsuccinimide ester (55750-63-5)

Guidance literature:

maleic anhydride; 6-aminohexanoic acid; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere;

1-hydroxy-pyrrolidine-2,5-dione; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1002/chem.201201670

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

6-(3-carboxyacryloylamino)caproic acid

di(succinimido) carbonate

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid

Downstream raw materials:

ethyl 2,3,4,6-tetra-O-[(6-(6-maleimidohexanamido)-3-thia-hexyl)]-α-D-galactopyranoside

C₆₈H₉₀ClN₉O₁₇

N-(N-doxorubicinhexanamide)maleimide

MC-MeVal-citrulline-p-aminobenzyl-OH

Refernces

• 1、 Hu, Xinyue,Jiang, Hailun,Bai, Weiqi,Liu, Xiujun,Miao, Qingfang,Wang, Linlin,Jin, Jie,Cui, Along,Liu, Rui,Li, Zhuorong. "Synthesis, characterization, and targeted chemotherapy of SCT200-linker-monomethyl auristatin E conjugates". . . Retrieved 2021/03/08.
• 2、 Danilko, Ksenia V.,Dyakonov, Grigory S.,Farrakhov, Ruzil G.,Galimshina, Zulfia R.,Gil'fanova, Guzel U.,Lukina, Elena S.,Mukaeva, Veta R.,Parfenov, Evgeny V.,Parfenova, Lyudmila V.. "Biocompatible organic coatings based on bisphosphonic acid RGD‐derivatives for PEO‐modified titanium implants". . . Retrieved 2020/01/13.