Click Chemistry

Introduced in 2001 by M. Meldal and nobel prize awarded in 2022, the Cu-catalyzed azide alkyne cycloaddition (CuAAC) gained enormous potential in peptide chemistry. An azide reacts with an alkyne moiety in order to form a stable triazole.

The fast reaction rate and the selectivity made it the most popular “click” reaction. Furthermore, this reaction proceeds without the formation of any side product in water and organic solvents. All these properties are very suitable for applications in biochemistry and particularly peptide chemistry.

Click chemistry with an alkyne functionalized peptide
Click chemistry with an azide functionalized peptide
CuACC inter-/intra-molecular

Biosyntan offers peptides with different azide or alkyne building blocks that can be incorporated at any position. Azide functionalized PEG spacers are available as well. Such a functionalization opens up an enormous variety of coupling reactions, e.g. labeling with dyes, attachment to surfaces or antibodies.

Building Blocks for CuACC

azido amino propionic acid
azido amino butyric acid
azido ornithine
azido lysine
propargyl glycine
pentynoic acid
azido pentanoic acid
azido PEG4

Cu-free Click Chemistry

Introduced by Bertozzi [1], the use of restrained alkine components make the copper catalyst obsolete. BIOSYNTAN offers the incorporation of DBCO coupled as free acid to amino groups or as maleimide to thiol groups.

[1] John C. Jewett and Carolyn R. Bertozzi, Chem Soc Rev. 2010 Apr; 39(4): 1272–1279.

DBCO
DBCO maleimide
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