Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

Rebecca R. Midtkandal; Philip Redpath; Samuel A J Trammell; Simon J F MacDonald; Charles Brenner; Marie E. Migaud

doi:10.1016/j.bmcl.2012.06.069

Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

Rebecca R. Midtkandal, Philip Redpath, Samuel A J Trammell, Simon J F MacDonald, Charles Brenner, Marie E. Migaud^*

^*Corresponding author for this work

4 Citations (Scopus)

Abstract

2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.

Original language	English
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	16
Pages (from-to)	5204-5207
Number of pages	4
ISSN	0960-894X
DOIs	https://doi.org/10.1016/j.bmcl.2012.06.069
Publication status	Published - 15 Aug 2012

Keywords

Benzamide riboside
C-Nucleoside
Inosine monophosphate dehydrogenase
Intramolecular cyclisation
Nicotinamide adenine dinucleotide

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10.1016/j.bmcl.2012.06.069

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title = "Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside",

abstract = "2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.",

keywords = "Benzamide riboside, C-Nucleoside, Inosine monophosphate dehydrogenase, Intramolecular cyclisation, Nicotinamide adenine dinucleotide",

author = "Midtkandal, {Rebecca R.} and Philip Redpath and Trammell, {Samuel A J} and MacDonald, {Simon J F} and Charles Brenner and Migaud, {Marie E.}",

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T1 - Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

AU - Midtkandal, Rebecca R.

AU - Redpath, Philip

AU - Trammell, Samuel A J

AU - MacDonald, Simon J F

AU - Brenner, Charles

AU - Migaud, Marie E.

PY - 2012/8/15

Y1 - 2012/8/15

N2 - 2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.

AB - 2-Deoxy-C-nucleosides are a subcategory of C-nucleosides that has not been explored extensively, largely because the synthesis is less facile. Flexible synthetic procedures giving access to 2-deoxy-C-nucleosides are therefore of interest. To exemplify the versatility and highlight the limitations of a synthetic route recently developed to that effect, the first synthesis of 2-deoxy benzamide riboside is reported. Biological properties of this novel C-nucleoside are also discussed.

KW - Benzamide riboside

KW - C-Nucleoside

KW - Inosine monophosphate dehydrogenase

KW - Intramolecular cyclisation

KW - Nicotinamide adenine dinucleotide

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U2 - 10.1016/j.bmcl.2012.06.069

DO - 10.1016/j.bmcl.2012.06.069

M3 - Journal article

C2 - 22795628

AN - SCOPUS:84864411406

SN - 0960-894X

VL - 22

SP - 5204

EP - 5207

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 16

ER -

Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside

Abstract

Keywords

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