DBCO-PEG4-SE

Base Information

• Chemical Name: DBCO-PEG4-SE
• CAS No.: 1427004-19-0
• Molecular Formula: C₃₄H₃₉N₃O₁₀
• Molecular Weight: 649.698
• Hs Code.: 2942000090
• Mol file: 1427004-19-0.mol

Synonyms:2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate

Chemical Property of DBCO-PEG4-SE

Chemical Property:

• PKA: 15.14±0.46(Predicted)
• Density: 1.33±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO, DCM, DMF

Purity/Quality:

98%,99%, ^*data from raw suppliers

DBCO-PEG4-NHSEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: DBCO-PEG4-NHS Ester is a click chemistry PEG reagent containing NHS ester that is able to react specifically and efficiently with primary amines (e.g. the side chain of lysine residues or aminosilane-coated surfaces) at neutral or slightly basic condition to form a covalent bond. The hydrophilic PEG spacer arm improves water solubility and provides a long and flexible connection that minimizes steric hindrance involved with ligation. DBCO is commonly used for copper-free Click Chemistry reactions.
• Uses: Succinimidyl ester (NHS, amine reactive) functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free click chemistry cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage. Applications Include: Protein-peptide conjugatesAntibody-enzyme or antibody-drug conjugatesProtein or peptide-oligonucleotide conjugates Surface modification

Technology Process of DBCO-PEG4-SE

There total 14 articles about DBCO-PEG4-SE 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: 84.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid (1537170-85-6,2353410-00-9) → 2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate (1427004-19-0,2093934-94-0)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 24h;

Reference yield:

dibenzosuberenon (2222-33-5) → 2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate (1427004-19-0,2093934-94-0)

Guidance literature:

Multi-step reaction with 8 steps

1: hydroxylamine hydrochloride; pyridine / ethanol / 15 h / Reflux

2: diisobutylaluminium hydride / dichloromethane; toluene / -5 - 20 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C

4: bromine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5: potassium tert-butylate / tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere

6: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

7: triethylamine / N,N-dimethyl-formamide / 20 °C

8: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With pyridine; hydroxylamine hydrochloride; potassium tert-butylate; bromine; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

N-[tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,9,12,14-heptaen-2-ylidene]hydroxylamine (1021-91-6) → 2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate (1427004-19-0,2093934-94-0)

Guidance literature:

Multi-step reaction with 7 steps

1: diisobutylaluminium hydride / dichloromethane; toluene / -5 - 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C

3: bromine / dichloromethane / 2 h / 0 °C / Inert atmosphere

4: potassium tert-butylate / tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

6: triethylamine / N,N-dimethyl-formamide / 20 °C

7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With potassium tert-butylate; bromine; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

1-(4-{2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid

dibenzosuberenon

N-[tricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,3,5,7,9,12,14-heptaen-2-ylidene]hydroxylamine