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

Joseph B. Sweeney, Paul A. Bethel, Duncan M. Gill, Agata M. Ochocińska, Anthony E.J. Walsh, Scarlett M. Walton

Research output: Contribution to journalLetter

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.

Original languageEnglish
Pages (from-to)2004-2007
Number of pages4
JournalOrganic Letters
Volume21
Issue number7
DOIs
Publication statusPublished - 12 Mar 2019

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nucleosides
Microwave irradiation
Nucleosides
reaction time
Amines
RNA
analogs
preparation
synthesis
amines
Microwaves
microwaves
irradiation
lysidine
isocytosine

Cite this

Sweeney, Joseph B. ; Bethel, Paul A. ; Gill, Duncan M. ; Ochocińska, Agata M. ; Walsh, Anthony E.J. ; Walton, Scarlett M. / Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides. In: Organic Letters. 2019 ; Vol. 21, No. 7. pp. 2004-2007.
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Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides. / Sweeney, Joseph B.; Bethel, Paul A.; Gill, Duncan M.; Ochocińska, Agata M.; Walsh, Anthony E.J.; Walton, Scarlett M.

In: Organic Letters, Vol. 21, No. 7, 12.03.2019, p. 2004-2007.

Research output: Contribution to journalLetter

TY - JOUR

T1 - Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides

AU - Sweeney, Joseph B.

AU - Bethel, Paul A.

AU - Gill, Duncan M.

AU - Ochocińska, Agata M.

AU - Walsh, Anthony E.J.

AU - Walton, Scarlett M.

PY - 2019/3/12

Y1 - 2019/3/12

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