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Bioconjug Chem. 2008 Apr;19(4):866-75. doi: 10.1021/bc700390r. Epub 2008 Mar 5.

Unnatural amino acid incorporation into virus-like particles.

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1
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.

Abstract

Virus-like particles composed of hepatitis B virus (HBV) or bacteriophage Qbeta capsid proteins have been labeled with azide- or alkyne-containing unnatural amino acids by expression in a methionine auxotrophic strain of E. coli. The substitution does not affect the ability of the particles to self-assemble into icosahedral structures indistinguishable from native forms. The azide and alkyne groups were addressed by Cu(I)-catalyzed [3 + 2] cycloaddition: HBV particles were decomposed by the formation of more than 120 triazole linkages per capsid in a location-dependent manner, whereas Qbeta suffered no such instability. The marriage of these well-known techniques of sense-codon reassignment and bioorthogonal chemical coupling provides the capability to construct polyvalent particles displaying a wide variety of functional groups with near-perfect control of spacing.

PMID:
18318461
PMCID:
PMC2713011
DOI:
10.1021/bc700390r
[Indexed for MEDLINE]
Free PMC Article
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