DBCO-NHS

Base Information

• Chemical Name: DBCO-NHS
• CAS No.: 1353016-71-3
• Molecular Formula: C₂₃H₁₈N₂O₅
• Molecular Weight: 402.406
• Hs Code.: 29339900
• Mol file: 1353016-71-3.mol

Synonyms:4-{2-azatricyclo[10.4.0.0⁴'⁹]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid

Chemical Property of DBCO-NHS

Chemical Property:

• Boiling Point: 670.2±65.0 °C(Predicted)
• PKA: -0.23±0.20(Predicted)
• Density: 1.43±0.1 g/cm3(Predicted)
• Solubility.: Soluble in DMSO, DCM, DMF

Purity/Quality:

99%, ^*data from raw suppliers

DBCO-NHSEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: DBCO-NHS Ester is a very popular amine-reactive click chemistry reagent. It can be used to modify an amine-containing molecule in organic solvents (limited solubility in aqueous media). It reacts with primary amines such as the side chain of lysine residues or aminosilane-coated surfaces at neutral or slightly basic pH to form covalent bonds. The low mass weight will add minimal spacer to modified molecules. DBCO is commonly used for copper-free Click Chemistry reactions.
• Uses: DBCO-NHS Ester is a derivative of DBCO (Dibenzylcyclooctyne), used in Cu-free click chemistry. It useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. Used in DNA-Assisted protein analysis such as proximity ligation and extention assays. Intracellular Imaging. DBCO NHS ester contains an NHS carbonate group and a DBCO group. The spacer contains a photocleavable nitrobenzyloxyl group, which can be efficiently cleaved under UV to release the conjugated molecules. DBCO on the other hand readily react with azide bearing biomolecule through a copper-free click reaction instantly and in high yield. DBCO-NHS Ester is a very popular amine-reactive click chemistry reagent. It can be used to modify an amine-containing molecule in organic solvents (limited solubility in aqueous media). It reacts with primary amines such as the side chain of lysine residues or aminosilane-coated surfaces at neutral or slightly basic pH to form covalent bonds. The low mass weight will add minimal spacer to modified molecules. DBCO is commonly used for copper-free Click Chemistry reactions.

Technology Process of DBCO-NHS

There total 13 articles about DBCO-NHS 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: 82.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(16),4(9),5,7,12,14-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-70-2) → 4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-71-3)

Guidance literature:

With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.201105547

Reference yield:

N-iodo-succinimide (516-12-1) + 4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(16),4(9),5,7,12,14-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-70-2) → 4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-71-3)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide;

Reference yield:

4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(16),4(9),5,7,12,14-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-70-2) → 4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-71-3)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1021/ja307713q

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

4-{2-azatricyclo[10.4.0.0⁴'⁹]hexadeca-1⁽¹⁶⁾,4⁽⁹⁾,5,7,12,14-hexaen-10-yn-2-yl}-4-oxobutanoic acid

dibenzo[b,f]azocin-6(5H)-one

2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹⁶⁾,4⁽⁹⁾,5,7,10,12,14-heptene

Downstream raw materials:

C₂₇H₂₃FN₄O₃

methyl 4-(1-(4-fluorophenyl)-1H-dibenzo[b,f][1,2,3]triazolo[4,5-d]azocin-8(9H)-yl)-4-oxobutanoate

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

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

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