Synthesis and Photophysical Characterization of a New, Highly Hydrophilic Caging Group

Abstract

Keywords: Caged compounds / Glutamate transporter / Natural products / Photochemistry o-Nitrobenzyl-protected bioactive compounds are useful tools in biophysics, allowing controlled photorelease of biologically active compounds with high temporal and spatial precision. Thus, it is possible to study biological processes, such as neurotransmitter-receptor interaction, and many other processes, in much more detail than before. In this respect, these caged compounds have become established as extremely useful tools. In some cases, however, their biological properties (the caged compound should not interact with the biological system), their photochemical properties (quantum yield and kinetics of the photorelease), and their physical properties (high hydrophilicity) are not satisfactory. In order

Photoprocesses of Molecules with 2‐Nitrobenzyl Protecting Groups and Caged Organic Acids

“…For 2‐nitrobenzyl benzoate 1b two isomers can be distinguished kinetically (6). Two components of the aci ‐nitro forms have also been proposed in other cases (13,14). It has been argued that the longer lived component of 1b is stabilized by the interaction of the α‐hydrogen with an oxygen of the AH form (6).…”

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

“…194 A related strategy (based on 75 ) had been devised by Schaper and co-workers. 195 Thiols could also be released with the derivative 76 . 196 A time-resolved infrared study of the photoreactivity of α-CNB 74 was performed by Corrie and co-workers.…”

The α,5‐Dicarboxy‐2‐nitrobenzyl Caging Group, a Tool for Biophysical Applications with Improved Hydrophilicity: Synthesis, Photochemical Properties and Biological Characterization

“…These compounds are due to their increased hydrophilicity advantageous compared with the well‐established α ‐CNB caged compounds ( 5 ). However, for α ,4‐DCNB caged compounds ( 7 ) the aci ‐nitro intermediate decays significantly slower than the respective aci ‐nitro intermediate for α ‐CNB caged compounds ( 5 ) (55). Thus the release of the active compound is slower.…”

“…However, the release of the active compound is slower for α ,4‐DCNB compared with α ‐CNB 5 (see Table 1 for more details). Based on our earlier theoretical predictions we assumed that we could increase the rate of release for the active compound by moving the carboxy group from the 4‐ to the 5‐position to give α ,5 ‐ d i c arboxy‐2‐ n itro b enzyl group ( α ,5‐DCNB 8 ) (55). Therefore we set out to synthesize a α ,5‐DCNB caged aspartate 17 .…”