The Art of Bioconjugation: Functionalization of VNPs - Viral Nanoparticles: Tools for Materials Science and Biomedicine - page 85

Figure 4.7 (A ) Introduction of an azide or alkyne functional group by coupling

and azide or alkyne derivative to an amine using a NHS ester, to a thiol using a
maleimide, or phenol ring using an aniline derivative. (B ) Reaction between an azide
and alkyne resuls in the formation of a triazole linkage. (C) Copper-binding ligands
used for click chemistry on VNPs: tris(triazoleylmethyl)amine (TBTA), THPTA, and
sulfonated bathophenanthroline. Figure provided by courtesy of Vu Hong (TSRI,
La Jolla, CA, USA).

4.2.2 Oxime Condensaion

The bio-orthogonal reaction between an aldehyde and hydrazide or alkoxya-
mine is also highly chemoselective and efficient; this reaction is termed as
oxime condensation. Oxime condensation reactions have been adapted
for the VNPs MS2 and TMV (Datta et al. , 2008; Hooker et al. , 2007, 2008;

Kovacs , 2005). In order to perform this reaction,

an aldehyde ligation handle is introduced into the VNP scaffold using either
an aldehyde-containing NHS-derivative and coupling to Lys side chains, or
an aldehyde-containing diazonium salt of

et al. , 2007; Schlick et al.

p -aniline and coupling to Tyr side