Fluorescein analogues as photoremovable protecting groups absorbing at ∼520 nm

J Org Chem. 2013 Mar 1;78(5):1833-43. doi: 10.1021/jo301455n. Epub 2012 Jul 31.

Abstract

A new photoremovable protecting group, (6-hydroxy-3-oxo-3H-xanthen-9-yl)methyl (1), with a molar absorption coefficient ε of ∼4 × 10(4) m(-1) cm(-1) at ∼520 nm for the release of carboxylates or phosphates is reported. Three derivatives of 1 (diethyl phosphate, acetate, and bromide) were isolated as complexes with DDQ and shown to release the ligands with quantum yields ≤2.4% in aqueous solution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Absorption
  • Fluorescein / chemistry*
  • Ligands
  • Molecular Structure
  • Photochemistry
  • Photolysis
  • Quantum Theory
  • Solutions / chemistry*
  • Xanthenes / chemistry*

Substances

  • (6-hydroxy-3-oxo-3H-xanthen-9-yl)methyl
  • Ligands
  • Solutions
  • Xanthenes
  • Fluorescein