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AutoClickChem: Click Chemistry in Silico

Figure 1

A schematic showing how AutoClickChem mimics the azide-alkyne Huisgen cycloaddition.

A) This cycloaddition combines an alkyne and an azide into a 1,2,3-triazole product. B) As a first step, AutoClickChem fragments the alkyne along its triple bond and the azide along the bond connecting its proximal and medial azide nitrogen atom. C) The fragments are then translated so that atomic “handles” are superimposed on top of the corresponding atoms of a 1,2,3-triazole model. D) Next, the fragments are rotated about the handle atoms in order to minimize the distance between the handle-adjacent atoms and the corresponding atoms on the 1,2,3-triazole model. E) The positioned fragments are then rotated in order to reduce steric hindrance. F) Finally, redundant atoms are deleted, and the fragment and 1,2,3-triazole model atoms are merged into a single final structure.

Figure 1

doi: https://doi.org/10.1371/journal.pcbi.1002397.g001