A minute amount of s-puckered sugars is sufficient for (6-4) photoproduct formation at the dinucleotide level

Céline Moriou; Clément Denhez; Oleksandr Plashkevych; Stéphanie Coantic-Castex; Jyoti Chattopadhyaya; Dominique Guillaume; Pascale Clivio

doi:10.1021/jo502230n

A minute amount of s-puckered sugars is sufficient for (6-4) photoproduct formation at the dinucleotide level

J Org Chem. 2015 Jan 2;80(1):615-9. doi: 10.1021/jo502230n. Epub 2014 Dec 11.

Authors

Céline Moriou¹, Clément Denhez², Oleksandr Plashkevych, Stéphanie Coantic-Castex², Jyoti Chattopadhyaya, Dominique Guillaume², Pascale Clivio²

Affiliations

¹ †Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
² ‡Université de Reims Champagne Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, UFR de Pharmacie, 51 rue Cognacq-Jay, 51096 Reims Cedex, France.

PMID: 25496131
DOI: 10.1021/jo502230n

Abstract

The di-2'-α-fluoro analogue of thymidylyl(3',5')thymidine, synthesized to probe the effect of a minimum amount of S conformer on the photoreactivity of dinucleotides, is endowed with only 3% and 8% of S sugar conformation at its 5'- and 3'-end, respectively. This analogue gives rise to the (6-4) photoproduct as efficiently as the dithymine dinucleotide (74% and 66% at the 5'- and 3'-end, respectively) under 254 nm. Our results suggest that the 5'-N, 3'-S conformer gives rise to the (6-4) photoproduct.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrates / chemistry*
Dinucleoside Phosphates / chemical synthesis*
Dinucleoside Phosphates / chemistry
Molecular Conformation
Photochemical Processes

Substances

Carbohydrates
Dinucleoside Phosphates
thymidylyl-(3'-5')-thymidine