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The Two Bioinorganic Projects of Research Methodology Fall 2012. Tetraphenyl porphyrin. Ligand Synthesis. Pteridinyl phenanthroline. Complex Synthesis. Biochemical Studies. Types of Pteridinyl Phenanthroline Ligands (and other). L-UN. L-amino. L- keto. DPPZ. L- allox.
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The Two Bioinorganic Projects of Research Methodology Fall 2012 Tetraphenylporphyrin Ligand Synthesis Pteridinyl phenanthroline Complex Synthesis Biochemical Studies
Types of PteridinylPhenanthroline Ligands (and other) L-UN L-amino L-keto DPPZ L-allox
Ligand Synthesis (by Alexandra) Pteridinylphenanthroline synthesis MeOH 20 h or so in NaOH pH ~11
Group and Ligand Assignments for Synthesis and Characterization Group # Students ligand complex Group 1 — Linda Cho, Katie GuyeDPPZ [Ru(bpy)2(DPPZ)](PF6)2 Group 2 — Rachael Kahlin,JuliaHeerL-allox [Ru(bpy)2(L-allox)](PF6)2 Group 3 — Julie Han,BingqingLi L-amino [Ru(bpy)2(L-amino)](PF6)2 Group 4 — Alicia Makepeace,MishaSims L-keto [Ru(bpy)2(L-keto)](PF6) Group 5 — Terry Huh,MariaNam L-keto [Ru(bpy)2(L-keto)](PF6)2 Group 6 — Anna Kalinsky,JanielleVidal L-keto (to make L-aap) [Ru(bpy)2(L-aap)](PF6)2 Group 7— Chloe Baumann,SaraKim L-UN (to make L-alap) [Ru(bpy)2(L-alap)](PF6)2 ‘Group’ 8 — Alexandra Kirsch L-tallox (thioalloxazine) [Ru(bpy)2(L-tallox)](PF6)2 L-UN L-amino L-keto DPPZ L-allox w/ Ru w/ Ru L-aap L-alap
Group and Ligand Assignments for Synthesis and Characterization Group # Students ligand complex Group 1 — Linda Cho, Katie GuyeDPPZ [Ru(bpy)2(DPPZ)](PF6)2 Group 2 — Rachael Kahlin,JuliaHeerL-allox [Ru(bpy)2(L-allox)](PF6)2 Group 3 — Julie Han,BingqingLi L-amino [Ru(bpy)2(L-amino)](PF6)2 Group 4 — Alicia Makepeace,MishaSims L-keto [Ru(bpy)2(L-keto)](PF6) Group 5 — Terry Huh,MariaNam L-keto [Ru(bpy)2(L-keto)](PF6)2 Group 6 — Anna Kalinsky,JanielleVidal L-keto (to make L-aap) [Ru(bpy)2(L-aap)](PF6)2 Group 7— Chloe Baumann,SaraKim L-UN (to make L-alap) [Ru(bpy)2(L-alap)](PF6)2 ‘Group’ 8 — Alexandra Kirsch L-tallox (thioalloxazine) [Ru(bpy)2(L-tallox)](PF6)2 L-UN L-amino L-keto DPPZ L-allox Phenylene diamine 5,6 –diamino 2,4 dihydroxy pyrimidine 5,6 –diamino 4-hydroxy pyrimidine 4,5,6 –triamino pyrimidine 5,6 –diamino pyrimidine
True or false? Blood is red because of the iron in hemoglobin. “Red blood cells” A close-up of red blood cells within a capillary. Over 99 percent of the blood vessels in the body are capillaries, even though they only hold 5 percent of the body’s blood.
False por·phy·rin Function: noun Etymology: from Greek porphyrapurple -any of various compounds with a macrocyclic structure that consists essentially of four pyrrole rings joined by four =CH- groups; especially : one (as chlorophyll or hemoglobin) containing a central metal atom and usually exhibiting biological activity
Nature’s synthesis of Porphyrin the pyrrole ring is formed Glycine + Succinyl CoA Protoporphyrin IX
The Adler synthesis of simple, symmetrically substituted porphyrins: Meso position R = phenyl (TPP) toluyl (TTP) p-chlorophenyl (TClPP)
Ligand Synthesis: Condensations are a Theme Schiff-Base Ligands