Next-Generation o-Nitrobenzyl Photolabile Groups for Light-Directed Chemistry and Microarray Synthesis

Nicole Kretschy; Ann-Katrin Holik; Veronika Somoza; Klaus-Peter Stengele; Mark M Somoza

doi:10.1002/anie.201502125

Next-Generation o-Nitrobenzyl Photolabile Groups for Light-Directed Chemistry and Microarray Synthesis

Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8555-9. doi: 10.1002/anie.201502125. Epub 2015 Jun 3.

Authors

Nicole Kretschy¹, Ann-Katrin Holik², Veronika Somoza^{2

3}, Klaus-Peter Stengele⁴, Mark M Somoza⁵

Affiliations

¹ Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Althanstrasse 14 (UZA II), 1090 Vienna (Austria).
² Department of Nutritional and Physiological Chemistry, Faculty of Chemistry, University of Vienna (Austria).
³ Christian Doppler Laboratory for Bioactive Aroma Compounds, University of Vienna (Austria).
⁴ Roche Diagnostics, Penzberg (Germany).
⁵ Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Althanstrasse 14 (UZA II), 1090 Vienna (Austria). [email protected].

Abstract

Light as an external trigger is a valuable and easily controllable tool for directing chemical reactions with high spatial and temporal accuracy. Two o-nitrobenzyl derivatives, benzoyl- and thiophenyl-NPPOC, undergo photo-deprotection with significantly improved efficiency over that of the commonly used NPPOC group. The two- and twelvefold increase in photo-deprotection efficiency was proven using photolithograph synthesis of microarrays.

Keywords: microarrays; photochemistry; photolysis; protecting groups.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Light
Microarray Analysis
Nitrobenzenes / chemistry*
Photolysis

Substances

Nitrobenzenes

Grants and funding

P 23797/FWF_/Austrian Science Fund FWF/Austria