Combinatorial Discovery of Two-Photon Photoremovable Protecting Groups

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...

Full description

Saved in:
Bibliographic Details
Published inProceedings of the National Academy of Sciences - PNAS Vol. 100; no. 22; pp. 12548 - 12553
Main Authors Pirrung, Michael C., Pieper, Wolfgang H., Kaliappan, Krishna P., Dhananjeyan, Mugunthu R.
Format Journal Article
LanguageEnglish
Published United States National Academy of Sciences 28.10.2003
National Acad Sciences
Subjects
Online AccessGet full text

Cover

Loading…
More Information
Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Edited by Nicholas J. Turro, Columbia University, New York, NY, and approved August 25, 2003
This paper was submitted directly (Track II) to the PNAS office.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.2131115100