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Dual-Surface Modification of the Tobacco Mosaic Virus
Abstract
The protein shell of the tobacco mosaic virus (TMV) provides a robust and practical tubelike scaffold for the preparation of nanoscale materials. To expand the range of applications for which the capsid can be used, two synthetic strategies have been developed for the attachment of new functionality to either the exterior or the interior surface of the virus. The first of these is accomplished using a highly efficient diazonium coupling/oxime formation sequence, which installs >2000 copies of a material component on the capsid exterior. Alternatively, the inner cavity of the tube can be modified by attaching amines to glutamic acid side chains through a carbodiimide coupling reaction. Both of these reactions have been demonstrated for a series of substrates, including biotin, chromophores, and crown ethers. Through the attachment of PEG polymers to the capsid exterior, organic-soluble TMV rods have been prepared. Finally, the orthogonality of these reactions has been demonstrated by installing different functional groups on the exterior and interior surfaces of the same capsid assemblies.
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Cited by
Yi, H., Wu, L.-Q., Bentley, W. E., Ghodssi, R., Rubloff, G. W., Culver, J. N., & Payne, G. F. (2005) · Biomacromolecules · doi:10.1021/bm050410l · Cited by 759
Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis
Kölmel, D. K., & Kool, E. T. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00090 · Cited by 699
In Situ Preparation of Protein−“Smart” Polymer Conjugates with Retention of Bioactivity
Heredia, K. L., Bontempo, D., Ly, T., Byers, J. T., Halstenberg, S., & Maynard, H. D. (2005) · Journal of the American Chemical Society · doi:10.1021/ja054482w · Cited by 451
Digital memory device based on tobacco mosaic virus conjugated with nanoparticles
Tseng, R. J., Tsai, C., Ma, L., Ouyang, J., Ozkan, C. S., & Yang, Y. (2006) · Nature Nanotechnology · doi:10.1038/nnano.2006.55 · Cited by 448
Stability of responsive polymer–protein bioconjugates
Shakya, A. K., Sami, H., Srivastava, A., & Kumar, A. (2010) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2010.01.003 · Cited by 110
Metadata
- Authors
- Schlick, T. L., Ding, Z., Kovacs, E. W., & Francis, M. B.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-02-23
- Volume
- 127
- Issue
- 11
- Pages
- 3718-3723
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2071300717
- Cited by
- 516
- References
- 0
- FWCI
- 16.15
- Type
- journal article
- Language
- en
- Open access
- closed
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- Schlick, T. L., Ding, Z., Kovacs, E. W., & Francis, M. B. (2005). Dual-Surface Modification of the Tobacco Mosaic Virus. Journal of the American Chemical Society. https://doi.org/10.1021/ja046239n
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