exo BCN-O-PNB Chemical Properties

Boiling point:

475.7±37.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Storage temp. 2-8°C

solubility 

good in DMF, DMSO, acetonitrile

form 

Solid

color 

White to off-white

Appearance

off-white solid

exo BCN-O-PNB Usage And Synthesis

Description

BCN-PNP carbonate is a tool to introduce BCN moety via carbamate linkage with primary amino groups of substrate. Reaction conditions is similar to NHS-amino linkage but PNP ester provides less off-target hydrolysis and higher conjugation yield forming hydrolytically stable bond with substrate.

Bicyclononyne (BCN) is one of the most reactive cyclooctynes for copper-free click chemistry. Both exo- and endo- isomers are active and have near the same power of reactions konstants [1,2]. BCN reacts even faster than DBCO [1] with aromatic azides and comparing to dibenzofused systems has two advantages. First, it contains a plane of symmetry which prevents the formation of mixtures of stereoisomeric products. Second, BCN provides lower lipophilicity which is typically more beneficial when reaction is performed in aqueous solutions. Unlike DBCO, BCN reactivity is not only limited to azides (SPAAC) and nitrones (SPANC), but also covers tetrazines (IEDDA) [2] and more recently tetrazoles (photoclick) [3] providing exceptional reaction rates.

Uses

exo BCN-O-PNB is an alkyl/ether-based PROTAC linker that can be used in the synthesis of PROTACs[1]. exo BCN-O-PNB is a click chemistry reagent, it contains a BCN group that can undergo strain-promoted alkyne-azide cycloaddition (SPAAC) with molecules containing Azide groups.

IC 50

Alkyl/ether

References

[1] An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562 DOI:10.1016/j.ebiom.2018.09.005

exo BCN-O-PNB(1380006-72-3)Related Product Information

• BCN-OH
• endo-BCN-PEG4-acid
• -
• endo BCN-O-PNB
• endo-BCN-PEG4-NHS ester
• -
• (1R,8S,9r)-bicyclo[6.1.0]nonan-9-ylmethanol