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    Rights statement: 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

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

Research output: Contribution to Journal/Magazine › Letter › peer-review

Published

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Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides. / Sweeney, J.B.; Bethel, P.A.; Gill, D.M. et al.
In: Organic Letters, Vol. 21, No. 7, 05.04.2019, p. 2004-2007.

Research output: Contribution to Journal/Magazine › Letter › peer-review

Harvard

Sweeney, JB, Bethel, PA, Gill, DM, Ochocińska, AM, Walsh, AEJ & Walton, SM 2019, 'Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides', Organic Letters, vol. 21, no. 7, pp. 2004-2007. https://doi.org/10.1021/acs.orglett.9b00086

APA

Sweeney, J. B., Bethel, P. A., Gill, D. M., Ochocińska, A. M., Walsh, A. E. J., & Walton, S. M. (2019). Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides. Organic Letters, 21(7), 2004-2007. https://doi.org/10.1021/acs.orglett.9b00086

Vancouver

Sweeney JB, Bethel PA, Gill DM, Ochocińska AM, Walsh AEJ, Walton SM. Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides. Organic Letters. 2019 Apr 5;21(7):2004-2007. Epub 2019 Mar 12. doi: 10.1021/acs.orglett.9b00086

Author

Sweeney, J.B. ; Bethel, P.A. ; Gill, D.M. et al. / 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.

Bibtex

@article{689190b6483d42dd96c8e755687bccd6,
title = "Synthesis of a protected keto-lysidine analogue via improved preparation of arabino-isocytosine nucleosides",
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.",
author = "J.B. Sweeney and P.A. Bethel and D.M. Gill and A.M. Ochoci{\'n}ska and A.E.J. Walsh and S.M. Walton",
note = "This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright {\textcopyright} 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",
year = "2019",
month = apr,
day = "5",
doi = "10.1021/acs.orglett.9b00086",
language = "English",
volume = "21",
pages = "2004--2007",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "7",

}

RIS

TY - JOUR

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

AU - Sweeney, J.B.

AU - Bethel, P.A.

AU - Gill, D.M.

AU - Ochocińska, A.M.

AU - Walsh, A.E.J.

AU - Walton, S.M.

N1 - 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

PY - 2019/4/5

Y1 - 2019/4/5

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.9b00086

DO - 10.1021/acs.orglett.9b00086

M3 - Letter

VL - 21

SP - 2004

EP - 2007

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 7

ER -