Issue 15, 2015
From the journal:

Chemical Communications

Selective arylthiolane deprotection by singlet oxygen: a promising tool for sensors and prodrugs†‡

Brian M. Lamb*abc  and  Carlos F. Barbas III§abc  

* Corresponding authors

a The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA, USA
E-mail: bmlamb@scripps.edu

b Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA

c The Scripps Research Institute, 10550 N. Torrey Pines Rd, La Jolla, CA, USA

Abstract

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.

Graphical abstract: Selective arylthiolane deprotection by singlet oxygen: a promising tool for sensors and prodrugs

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Article information

DOI
https://doi.org/10.1039/C4CC09040C
Article type
Communication
Submitted
12 Nov 2014
Accepted
09 Jan 2015
First published
21 Jan 2015

Chem. Commun., 2015,51, 3196-3199

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Selective arylthiolane deprotection by singlet oxygen: a promising tool for sensors and prodrugs

B. M. Lamb and C. F. Barbas III, Chem. Commun., 2015, 51, 3196 DOI: 10.1039/C4CC09040C

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