Interior surface modification of bacteriophage MS2 - PubMed (original) (raw)
. 2004 Mar 31;126(12):3718-9.
doi: 10.1021/ja031790q.
Affiliations
- PMID: 15038717
- DOI: 10.1021/ja031790q
Interior surface modification of bacteriophage MS2
Jacob M Hooker et al. J Am Chem Soc. 2004.
Abstract
An efficient strategy for the interior surface functionalization of MS2 viral capsids is reported, featuring a new hetero-Diels-Alder bioconjugation reaction. After virus isolation, the RNA genome was removed from the spherical particles by exposure to pH 11.8 conditions for a period of 4 h. Following this, 180 tyrosine residues on the interior surface of each "empty" capsid shell were modified by using a site-selective diazonium-coupling reaction. To attach additional functionality, the azo conjugate was reduced with Na2S2O4 to afford an ortho-amino tyrosine derivative. Oxidation of this moiety with NaIO4 produced an o-iminoquinone on the protein surface, which was found to undergo an efficient hetero-Diels-Alder reaction with N-(4-aminophenyl)acrylamide. This four-step procedure can be carried out in under 4 h, reaches high levels of conversion, and yields the desired conjugates in >60% overall yield.
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