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chains (Fig. 4.8, panel A). In the subsequent step, a hydrazide or alkoxyamine
derivative of the compound of interest is added and covalently attached via
the formation of a stable oxime bond (Fig. 4.8, panel B). For example, PEG
chains and chelated gadolinium complexes have been attached to MS2 and
TMV using this coupling strategy (Datta
et al.
, 2008; Hooker
et al.
, 2007;
Kovacs
, 2005). A high-yielding and improved ligation
approach has been developed that utilizes aniline as a catalyst to activate
aromatic aldehydes toward amine nucleophiles (Dirksen & Dawson, 2008).
et al.
, 2007; Schlick
et al.
Figure 4.8
Oxime condensation reaction. (A) Attachment of an aldehyde to a Lys
or Tyr side chain. (B ) Oxime condensation between an aldehyde and alkoxyamine.
Figure provided by courtesy of Vu Hong (TSRI, La Jolla, CA, USA).
.  eXAMPleS And hIghlIghtS: AddreSSABle VnPs
A large variety of VNP building blocks have been utilized for bioconjugation
strategies. Initial studies were concerned with the exploration of different
coupling strategies. Standard chemistries using commercially available
probes have been applied to nearly any VNP currently in use for
nanotechnology. More advanced protocols facilitating the attachment and
functionalization with nearly any chemical moiety within to intact proteins
and other nanomaterials have also been developed. The following sections
will give an overview of the addressable surface groups available on the
different VNPs. Examples and highlights will be given; Table 4.1 at the end
of this chapter will give an overview of the functional groups that have been
attached to VNPs. This chapter will focus on the specifics of the chemical
functionalization reaction. Applications of such modified hybrid VNP
complexes are also given.
 
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