Journal
CHEMICAL SCIENCE
Volume 5, Issue 10, Pages 3770-3776Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4sc01348d
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Funding
- National Science Foundation [NSF CHE1112409]
- National Institutes of Health [R01 EB014354, R01 GM068640-S]
- NIH [P20RR017716, S10 RR026962]
- NSF [CHE0840401, CHE-1229234]
- Medical Research Council, UK [U105181009, UD99999908]
- Medical Research Council
- MRC [MC_U105181009, MC_UP_A024_1008] Funding Source: UKRI
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1112409, 1229234] Funding Source: National Science Foundation
- Medical Research Council [MC_U105181009, MC_UP_A024_1008] Funding Source: researchfish
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Computation has guided the design of conformationally-strained dioxolane-fused trans-cyclooctene (d-TCO) derivatives that display excellent reactivity in the tetrazine ligation. A water soluble derivative of 3,6-dipyridyl-s-tetrazine reacts with d-TCO with a second order rate k(2) 366 000 (+/- 15 000) M-1 s(-1) at 25 degrees C in pure water. Furthermore, d-TCO derivatives can be prepared easily, are accessed through diastereoselective synthesis, and are typically crystalline bench-stable solids that are stable in aqueous solution, blood serum, or in the presence of thiols in buffered solution. GFP with a genetically encoded tetrazine-containing amino acid was site-specifically labelled in vivo by a d-TCO derivative. The fastest bioorthogonal reaction reported to date [k(2) 3 300 000 (+/- 40 000) M-1 s(-1) in H2O at 25 degrees C] is described herein with a cyclopropane-fused trans-cyclooctene. d-TCO derivatives display rates within an order of magnitude of these fastest trans-cyclooctene reagents, and also display enhanced stability and aqueous solubility.
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