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True or false? Blood is red because of the iron in hemoglobin.

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

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True or false? Blood is red because of the iron in hemoglobin.

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  1. 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.

  2. 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

  3. Wikipedia’s dynamic picture

  4. There are many different hemes used in biochemistry as: • Electron transfer cofactors as Fe(3+) / Fe(2+) • Catalytic Cofactors as cytochrome P450 • Besides O2 transport as hemoglobin

  5. One example: Cytochrome c Oxidase Where dioxygen is reduced to water during respiration Note all the hemes!

  6. How to draw a porphyrin:

  7. The Adler synthesis of simple, symmetrically substituted porphyrins: Meso position R = phenyl (TPP) toluyl (TTP) p-chlorophenyl (TClPP)

  8. Metallation of porphyrin Anything change at Fe? How do you know when the reaction is done? Porphyrin substituents on heme in hemoglobin

  9. Absorption Spectrum of a Porphyrin Figure 1. Typical UV-Vis absorption spectrum of a porphyrin. The highly conjugated porphyrin macrocycle shows intense absorption (extinction coefficient > 200,000 M-1cm-1) at around 400 nm (the "Soret" band), followed by several weaker absorption bands (Q Bands) at higher wavelengths (450 to 700 nm).

  10. 1H NMR Characterization: Challenges…. and how to meet them

  11. L- keto

  12. Ru(L-amino) Ru(L-keto) Ru(L-allox) ppm

  13. Complicated spectrum? Try 2-D COSY NMR (correlation spectroscopy)

  14. from Ben Williams

  15. from Ben Williams

  16. from Ben Williams

  17. from Ben Williams ,aʹ b a,bʹ c cʹ 1 2 ppm

  18. from Alex Gaudette. BMC’12

  19. d a,b,bʹ Ru(L-amino) 3 cʹ aʹ c d ,aʹ a b,bʹ Ru(L-keto) c cʹ ,aʹ Ru(L-allox) a c cʹ b,bʹ ppm

  20. For Thursday, Sept. 27: • Do heme synthesis using your prophyrin, TPP, TTP or TClPP, determining reaction completion by fluorescence • Filter Ru complex (if necessary); obtain MS of product • Observe 2D COSY NMR process • Obtain UV/vis spectrum of your Fe(porphyrin)Cl complex

  21. Writing Assignments • Goal = writing a full synthesis and characterization manuscript on the Ru complex you made • Structure like those we discussed on first day • Includes, synthesis, 1D NMR and 2D COSY, and CV • Due dates • Draft 1 on Wednesday Oct.3 of the Experimental Section with outline form of introduction • Draft 2 on Wednesday Oct. 10: Introduction, revised Expermental and Results section with NMR Results

  22. ,aʹ b a,bʹ c cʹ 1 2 Ru(L-aap) d a,b,bʹ 3 cʹ aʹ c Ru(L-amino) d ,aʹ a b,bʹ c cʹ Ru(L-keto) ppm

  23. ,aʹ b a,bʹ Ru(L-aap) c cʹ 1 2 d a,b,bʹ Ru(L-amino) 3 cʹ aʹ c d ,aʹ a b,bʹ Ru(L-keto) c cʹ ,aʹ Ru(L-allox) a c cʹ b,bʹ ppm

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