Selective arylthiolane deprotection by singlet oxygen: a promising tool for sensors and prodrugs.
- Resource Type
- Article
- Authors
- Lamb, Brian M.; Barbas III, Carlos F.
- Source
- Chemical Communications. 2015, Vol. 51 Issue 15, p3196-3199. 4p.
- Subject
- *REACTIVE oxygen species
*PRODRUGS
*PHOTODYNAMIC therapy
*SINGLE electron transfer mechanisms
*PHOTOINDUCED electron transfer
*KETONES
- Language
- ISSN
- 1359-7345
A routine thioketal protecting group reacts rapidly and selectively with singlet oxygen to reveal ketone products in good (aryl 1,3-dithiolane) to excellent (aryl 1,3-oxathiolane) yields. Arylthiolanes are stable to biologically relevant reactive oxygen species and can be used as a light-activated gating mechanism for activating fluorescent sensors or small molecule prodrugs. [ABSTRACT FROM AUTHOR]