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Design and Synthesis of Highly Reactive Dienophiles for the Tetrazine– trans- Cyclooctene Ligation
Open accessAbstract
Computation was used to design a trans-cyclooctene derivative that displays enhanced reactivity in the tetrazine-trans-cycloctene ligation. The optimized derivative is an (E)-bicyclo[6.1.0]non-4-ene with a cis-ring fusion, in which the eight-membered ring is forced to adopt a highly strained 'half-chair' conformation. Toward 3,6-dipyridyl-s-tetrazine in MeOH at 25 °C, the strained derivative is 19 and 27 times more reactive than the parent trans-cyclooctene and 4E-cyclooct-4-enol, respectively. Toward 3,6-diphenyl-s-tetrazine in MeOH at 25 °C, the strained derivative is 160 times more reactive than the parent trans-cyclooctene.
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Cites
Reactivity of biologically important thiol compounds with superoxide and hydrogen peroxide
Winterbourn, C. C., & Metodiewa, D. (1999) · Free Radical Biology and Medicine · doi:10.1016/s0891-5849(99)00051-9 · Cited by 799
Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones
Jewett, J. C., Sletten, E. M., & Bertozzi, C. R. (2010) · Journal of the American Chemical Society · doi:10.1021/ja100014q · Cited by 697
Cited by
Bioorthogonal Reactions for Labeling Proteins
Lang, K., & Chin, J. W. (2014) · ACS Chemical Biology · doi:10.1021/cb4009292 · Cited by 555
Metadata
- Authors
- Taylor, M. T., Blackman, M. L., Dmitrenko, O., & Fox, J. M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-06-06
- Volume
- 133
- Issue
- 25
- Pages
- 9646-9649
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2055706807
- Cited by
- 357
- References
- 2
- FWCI
- 12.57
- Type
- journal article
- Language
- en
- Open access
- green
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