Stereoselective Synthesis of β-Glycinamide Ribonucleotide

Lisa Ngu; Debarpita Ray; Samantha S. Watson; Penny J. Beuning; Mary Jo Ondrechen; George A. O’Doherty

doi:10.3390/molecules27082528

Molecules (Apr 2022)

Stereoselective Synthesis of β-Glycinamide Ribonucleotide

Lisa Ngu,
Debarpita Ray,
Samantha S. Watson,
Penny J. Beuning,
Mary Jo Ondrechen,
George A. O’Doherty

Affiliations

Lisa Ngu: Department of Chemistry, Northeastern University, Boston, MA 02115, USA
Debarpita Ray: Department of Chemistry, Northeastern University, Boston, MA 02115, USA
Samantha S. Watson: Department of Chemistry, Northeastern University, Boston, MA 02115, USA
Penny J. Beuning: Department of Chemistry, Northeastern University, Boston, MA 02115, USA
Mary Jo Ondrechen: Department of Chemistry, Northeastern University, Boston, MA 02115, USA
George A. O’Doherty: Department of Chemistry, Northeastern University, Boston, MA 02115, USA

DOI: https://doi.org/10.3390/molecules27082528
Journal volume & issue: Vol. 27, no. 8
p. 2528

Abstract

Read online

A diastereoselective synthesis of the β-anomer of glycinamide ribonucleotide (β-GAR) has been developed. The synthesis was accomplished in nine steps from D-ribose and occurred in 5% overall yield. The route provided material on the multi-milligram scale. The synthetic β-GAR formed was remarkably resistant to anomerization both in solution and as a solid.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

About the journal

Abstract

Keywords