761524
Dibenzocyclooctyne-N-hydroxysuccinimidyl ester
for Copper-free Click Chemistry
Synonym(s):
DBCO-NHS ester, DBCO-SE
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About This Item
Empirical Formula (Hill Notation):
C23H18N2O5
Molecular Weight:
402.40
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352108
MDL number:
Form:
solid
Quality Segment
form
solid
reaction suitability
reaction type: click chemistry, reagent type: cross-linking reagent
mp
149-157 (decomposition)
functional group
NHS ester
storage temp.
−20°C
SMILES string
O=C(CCC(ON(C(CC1)=O)C1=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4
InChI
1S/C23H18N2O5/c26-20(13-14-23(29)30-25-21(27)11-12-22(25)28)24-15-18-7-2-1-5-16(18)9-10-17-6-3-4-8-19(17)24/h1-8H,11-15H2
InChI key
XCEBOJWFQSQZKR-UHFFFAOYSA-N
General description
DBCO-NHS ester is commonly used in bioconjugation. It consists of an NHS ester that reacts with primary amines on biomolecules and an alkyne group that allows for a specific reaction with molecules containing azides. This reaction is carried out through a copper-free click chemistry process called strain-promoted alkyne-azide cycloaddition.
Application
Dibenzocyclooctyne-N-hydroxysuccinimidyl ester is commonly used:
- In the modification and labeling of biomolecules such as antibodies and streptavidin by introducing DBCO groups onto their surfaces
- As a cross linker to conjugate peptide antigens onto the surface of poly(lactic-co-glycolic acid) (PLGA) nanoparticles
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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