Exo-BCN-PNP

Cycloalkynes

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4043-100mg	100 mg	$280	in stock
4043-500mg	500 mg	$990	in stock

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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.

[1] Jan Dommerholt et al. Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells. Angewandte Chemie. 2010. 49(49). 9422-9425.

[2] Wagner et al. Origin of Orthogonality of Strain-Promoted Click Reactions. Chemistry. 2015. 21(35).12431-12435.

[3] Gangam Srikanth Kumar et al. Superfast Tetrazole–BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells. Journal of the American Chemical Society. 2022. 144(1). 57-62.

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General properties

Appearance:	off-white solid
Molecular weight:	315.32
Molecular formula:	C₁₇H₁₇NO₅
Solubility:	good in DMF, DMSO, acetonitrile
Quality control:	NMR ¹H and HPLC-MS (95+%)
Storage conditions:	24 months after receival at -20°C in the dark. Transportation: at room temperature for up to 3 weeks. Desiccate.
MSDS:	Download
	Product specifications

This Product is offered and sold for research purposes only. It has not been tested for safety and efficacy in food, drug, medical device, cosmetic, commercial or any other use. Supply does not express or imply authorization to use for any other purpose, including, without limitation, in vitro diagnostic purposes, in the manufacture of food or pharmaceutical products, in medical devices or in cosmetic products.

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