1246560-71-3Relevant academic research and scientific papers
Connection of metallamacrocycles via dynamic covalent chemistry: A versatile method for the synthesis of molecular cages
Granzhan, Anton,Schouwey, Clement,Riis-Johannessen, Thomas,Scopelliti, Rosario,Severin, Kay
supporting information; experimental part, p. 7106 - 7115 (2011/06/26)
A modular approach for the synthesis of cage structures is described. Reactions of [(arene)RuCl2]2 [arene = p-cymene, 1,3,5-C6H3Me3, 1,3,5-C6H 3(i-Pr)3] with formylsub
Rational design, synthesis and evaluation of first generation inhibitors of the Giardia lamblia fructose-1,6-biphosphate aldolase
Li, Zhimin,Liu, Zhengang,Cho, Dae Won,Zou, Jiwen,Gong, Maozhen,Breece, Robert M.,Galkin, Andrey,Li, Ling,Zhao, Hong,Maestas, Gabriel D.,Tierney, David L.,Herzberg, Osnat,Dunaway-Mariano, Debra,Mariano, Patrick S.
, p. 509 - 517 (2012/04/23)
Inhibitors of the Giardia lamblia fructose 1,6-bisphosphate aldolase (GlFBPA), which transforms fructose 1,6-bisphosphate (FBP) to dihydroxyacetone phosphate and glyceraldehyde 3-phosphate, were designed based on 3-hydroxy-2-pyridone and 1,2-dihydroxypyridine scaffolds that position two negatively charged tetrahedral groups for interaction with substrate phosphate binding residues, a hydrogen bond donor to the catalytic Asp83, and a Zn 2+ binding group. The inhibition activities for the GlFBPA catalyzed reaction of FBP of the prepared alkyl phosphonate/phosphate substituted 3-hydroxy-2-pyridinones and a dihydroxypyridine were determined. The 3-hydroxy-2-pyridone inhibitor 8 was found to bind to GlFBPA with an affinity (Ki = 14 μM) that is comparable to that of FBP (Km = 2 μM) or its inert analog TBP (Ki = 1 μM). The X-ray structure of the GlFBPA-inhibitor 8 complex (2.3 A?) shows that 8 binds to the active site in the manner predicted by in silico docking with the exception of coordination with Zn2+. The observed distances and orientation of the pyridone ring O=C-C-OH relative to Zn2+ are not consistent with a strong interaction. To determine if Zn2+coordination occurs in the GlFBPA-inhibitor 8 complex in solution, EXAFS spectra were measured. A four coordinate geometry comprised of the three enzyme histidine ligands and an oxygen atom from the pyridone ring O=C-C-OH was indicated. Analysis of the Zn2+ coordination geometries in recently reported structures of class II FBPAs suggests that strong Zn2+ coordination is reserved for the enediolate-like transition state, accounting for minimal contribution of Zn 2+ coordination to binding of 8 to GlFBPA.
Combining metallasupramolecular chemistry with dynamic covalent chemistry: Synthesis of large molecular cages
Granzhan, Anton,Riis-Johannessen, Thomas,Scopelliti, Rosario,Severin, Kay
supporting information; experimental part, p. 5515 - 5518 (2010/09/16)
(Figure Presented) Ru-built cube: By combining metallasupramolecular chemistry with dynamic covalent chemistry, complex nanostructures can be formed. Large cages are synthesized by reaction of trinuclear metallamacrocycles containing pendant aldehyde groups (see picture; Ru blue, aldehyde linkers green) with triamines (red).
