Pirrung, Michael C. ; Pieper, Wolfgang H. ; Kaliappan, Krishna P. ; Dhananjeyan, Mugunthu R. (2003) Combinatorial discovery of two-photon photoremovable protecting groups Proceedings of the National Academy of Sciences of the United States of America, 100 (22). pp. 12548-12553. ISSN 0027-8424
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Official URL: http://www.pnas.org/content/100/22/12548.abstract
Related URL: http://dx.doi.org/10.1073/pnas.2131115100
Abstract
A design principle for a two-photon photochemically removable protecting group based on sequential one-photon processes has been established. The expected performance of such groups in spatially directed photoactivation/photodeprotection has been shown by a kinetic analysis. One particular molecular class fitting into this design, the nitrobenzyl ethers of o-hydroxycinnamates, has been presented. An initial demonstration of two-photon deprotection of one such group prompted further optimization with respect to photochemical deprotection rate. This was accomplished by the preparation and screening of a 135-member indexed combinatorial library. Optimum performance for λ > 350 nm deprotection in organic solvent was found with 4,5-dialkoxy and α-cyano substitution in the nitrobenzyl group and 4-methoxy substitution in the cinnamate.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to National Academy of Sciences, USA. |
| ID Code: | 104836 |
| Deposited On: | 07 Jun 2017 20:37 |
| Last Modified: | 07 Jun 2017 20:37 |
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