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

Lobsiger, Simon; Blaser, Susan; Sinha, Rajeev K.; Frey, Hans-Martin; Leutwyler, Samuel (2014). Switching on the fluorescence of 2-aminopurine by site-selective microhydration. Nature chemistry, 6(11), pp. 989-993. Nature Publishing Group 10.1038/NCHEM.2086

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​2-Aminopurine (​2AP) 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 ​2AP 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, 2AP·(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.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Lobsiger, Simon; Blaser, Susan; Frey, Hans-Martin and Leutwyler, Samuel

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry
500 Science

ISSN:

1755-4330

Publisher:

Nature Publishing Group

Language:

English

Submitter:

Beatrice Niederhauser

Date Deposited:

25 Mar 2015 14:41

Last Modified:

25 Aug 2015 10:25

Publisher DOI:

10.1038/NCHEM.2086

BORIS DOI:

10.7892/boris.65782

URI:

https://boris.unibe.ch/id/eprint/65782

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