E.M.S. was supported by a predoctoral fellowship from the American Chemical Society Division of Organic Chemistry (Genentech). H.N. was partially supported by the Amgen Scholars Program. This work was supported by a grant to C.R.B. from the NIH (GM58867).
Thiacycloalkynes for Copper-Free Click Chemistry†
Version of Record online: 26 JAN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 10, pages 2443–2447, March 5, 2012
How to Cite
de Almeida, G., Sletten, E. M., Nakamura, H., Palaniappan, K. K. and Bertozzi, C. R. (2012), Thiacycloalkynes for Copper-Free Click Chemistry . Angew. Chem. Int. Ed., 51: 2443–2447. doi: 10.1002/anie.201106325
- Issue online: 1 MAR 2012
- Version of Record online: 26 JAN 2012
- Manuscript Revised: 30 NOV 2011
- Manuscript Received: 7 SEP 2011
- NIH. Grant Number: GM58867
- 11As an example, we prepared known 3,4-benzocyclononyne and found its rate constant for the dipolar cycloaddition with benzyl azide in CD3CN to be approximately 10−5 M−1 s−1, which is almost three orders of magnitude lower than that of the analogous cyclooctyne (see Ref. ). The preparation of this cyclononyne is reported in , , , Synlett 1994, 107.
- 14Despite the decreased reaction kinetics, thiaOCT (8) showed azide-dependent labeling on live cells with no cytotoxic effects (see Figures S10–S14 in the Supporting Information).
- 15aLiebigs Ann. Chem. 1974, 2074;, ,
- 15bTetrahedron Lett. 1970, 11, 761., ,
- 20Oxidizing the sulfide to a sulfoxide or sulfone may increase the hydrophilicity of these compounds, which is desirable, given the limited solubility of 10 in water.