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. Author manuscript; available in PMC: 2014 May 17.
Published in final edited form as: J Org Chem. 2013 Apr 30;78(10):4730–4743. doi: 10.1021/jo400192e

Figure 1.

Figure 1

a. Detail of the crystal structure of GlcN6P bound to the glmS riboyzme.11 Green and red spheres represent a magnesium ion and water molecules, respectively. Dotted lines indicate hydrogen bonds. GlcN6P stacks under the nucleobase of RNA residue G1, with its anomeric oxygen participating in hydrogen bonding interactions with the scissile phosphate (*), G65 and G66. The catalytically critical amine of GlcN6P hydrogen bonds with the 5′-O of G1, the base of U51, and a well-ordered water molecule. The hydroxyls at positions 3 and 4 of GlcN6P make direct and water-mediated hydrogen bonds with backbone atoms of A50 and U51. The O4 of GlcN6P receives a hydrogen bond from the nucleobase of C2. Finally, the N1 amide of G1 hydrogen bonds to the phosphate of the small molecule. Figure 1b. Previously described GlcN6P analogues and their effectiveness as coenzymes for the glmS ribozyme. (-) = inactive; (+) = weakly active; (++) modestly active; (+++) = strongly active.