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

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

Journal article

Open access

Peer reviewed

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 and Marie E Migaud

Bioorganic & Medicinal Chemistry Letters, Vol.22(16), pp.5204-5207

08/15/2012

DOI: 10.1016/j.bmcl.2012.06.069

PMCID: PMC3683580

PMID: 22795628

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https://www.ncbi.nlm.nih.gov/pmc/articles/3683580View

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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.

Nicotinamide adenine dinucleotide

Benzamide riboside

Inosine monophosphate dehydrogenase

C-Nucleoside

Intramolecular cyclisation

Details

Title: Subtitle: Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside
Creators: Rebecca R Midtkandal - Queen’s University Belfast, John King Laboratory, School of Pharmacy, Lisburn Road, Belfast, BT9 7BL, Northern Ireland, UK
Philip Redpath - Queen’s University Belfast, John King Laboratory, School of Pharmacy, Lisburn Road, Belfast, BT9 7BL, Northern Ireland, UK
Samuel A.J Trammell - University of Iowa, Department of Biochemistry, Carver College of Medicine, 51 Newton Rd, 4-403 BSB, Iowa City, IA 52242, USA
Simon J.F Macdonald - GlaxoSmithKline, Stevenage, SG1 2NY, UK
Charles Brenner - University of Iowa, Department of Biochemistry, Carver College of Medicine, 51 Newton Rd, 4-403 BSB, Iowa City, IA 52242, USA
Marie E Migaud - Queen’s University Belfast, John King Laboratory, School of Pharmacy, Lisburn Road, Belfast, BT9 7BL, Northern Ireland, UK
Resource Type: Journal article
Publication Details: Bioorganic & Medicinal Chemistry Letters, Vol.22(16), pp.5204-5207
DOI: 10.1016/j.bmcl.2012.06.069
PMID: 22795628
PMCID: PMC3683580
NLM abbreviation: Bioorg Med Chem Lett
ISSN: 0960-894X
eISSN: 1464-3405
Publisher: Elsevier Ltd
Language: English
Date published: 08/15/2012
Academic Unit: Biochemistry and Molecular Biology; Internal Medicine
Record Identifier: 9983788597402771

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