Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides

Sweeney, J.B. and Bethel, P.A. and Gill, D.M. and Ochocińska, A.M. and Walsh, A.E.J. and Walton, S.M. (2019) Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides. Organic Letters, 21 (7). pp. 2004-2007. ISSN 1523-7060

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Abstract

Anhydrouridines react with aliphatic amines to give N-alkyl isocytosines, but reported procedures often demand very long reaction times and can be low yielding, with narrow scope. A modified procedure for such reactions has been developed, using microwave irradiation, significantly reducing reaction time and allowing facile access to a diverse range of novel nucleosides on the gram scale. The method has been used to prepare a precursor to a novel analogue of lysidine, a naturally occurring iminonucleoside found in (t)RNA.

Item Type:

Journal Article

Journal or Publication Title:

Organic Letters

Additional Information:

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.9b00086

Uncontrolled Keywords:

/dk/atira/pure/subjectarea/asjc/1300/1303

Subjects:

?? biochemistryorganic chemistryphysical and theoretical chemistry ??

ID Code:

133191

Deposited By:

ep_importer_pure

Deposited On:

22 Jun 2019 09:09

Refereed?:

Yes

Published?:

Published

Last Modified:

21 Dec 2024 01:49

URI:

https://eprints.lancs.ac.uk/id/eprint/133191