Switching on the fluorescence of 2-aminopurine by site-selective microhydration

Simon Lobsiger, Susan Blaser, Rajeev K. Sinha, Hans Martin Frey, Samuel Leutwyler

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

2-Aminopurine (2 AP) is a fluorescent isomer of adenine and has a fluorescence lifetime of ~11 ns in water. It is widely used in biochemical settings as a site-specific fluorescent probe of DNA and RNA structure and base-flipping and -folding. These assays assume that 2 AP is intrinsically strongly fluorescent. Here, we show this not to be the case, observing that gas-phase, jet-cooled 2-aminopurine and 9-methyl-2-aminopurine have very short fluorescence lifetimes (156 ps and 210 ps, respectively); they are, to all intents and purposes, non-fluorescent. We find that the lifetime of 2-aminopurine increases dramatically when it is part of a hydrate cluster, 2 AP · (H2O)n, where n = 1-3. Not only does it depend on the presence of water molecules, it also depends on the specific hydrogen-bonding site to which they attach and on the number of H2O molecules at that site. We selectively microhydrate 2-aminopurine at its sugar-edge, cis-amino or trans-amino sites and see that its fluorescence lifetime increases by 4, 50 and 95 times (to 14.5 ns), respectively.

Original languageEnglish
Pages (from-to)989-993
Number of pages5
JournalNature Chemistry
Volume6
Issue number11
DOIs
Publication statusPublished - 01-11-2014

Fingerprint

2-Aminopurine
Fluorescence
Molecules
Hydrates
RNA
Sugars
Isomers
Water
Assays
Hydrogen bonds
DNA
Gases
Adenine
Hydrogen Bonding
Fluorescent Dyes

All Science Journal Classification (ASJC) codes

  • Medicine(all)

Cite this

Lobsiger, Simon ; Blaser, Susan ; Sinha, Rajeev K. ; Frey, Hans Martin ; Leutwyler, Samuel. / Switching on the fluorescence of 2-aminopurine by site-selective microhydration. In: Nature Chemistry. 2014 ; Vol. 6, No. 11. pp. 989-993.
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Switching on the fluorescence of 2-aminopurine by site-selective microhydration. / Lobsiger, Simon; Blaser, Susan; Sinha, Rajeev K.; Frey, Hans Martin; Leutwyler, Samuel.

In: Nature Chemistry, Vol. 6, No. 11, 01.11.2014, p. 989-993.

Research output: Contribution to journalArticle

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