Combinatorial discovery of two-photon photoremovable protecting groups
2003; National Academy of Sciences; Volume: 100; Issue: 22 Linguagem: Inglês
10.1073/pnas.2131115100
ISSN1091-6490
AutoresMichael C. Pirrung, Wolfgang H. Pieper, Krishna P. Kaliappan, Mugunthu R. Dhananjeyan,
Tópico(s)Nonlinear Optical Materials Studies
ResumoA 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.
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