Dissertation Synthesis

iii TABLE F CTETS DEDICATI..ACKWLEDGEMETS..LIST F TABLES..LIST F FIGURES..LIST F ABBREVIATIS..ABSTRACT..CAPTER 1.

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Frank Fronczek for crystal structure determinations and to Dr. The solid-phase linkage was investigated based on the stability of the ferrocenium ion.

FAB FAL Fmoc Fmoc-Cl GFP h ATU BTU Br Cl F MPV At Diisopropylcarbodiimide 4-Dimehtylaminopyridine,-dimethylformamide Dimethylsulfoxide Dimethoxytrityl Delayed-type hypersensitivity Dithiasuccinoyl Diethyl Ether Ethyl Acetate Equivalents Fast atom bombardment rrocenyl amine linker 9-Fluorenylmethyloxycarbonyl 9-Fluorenylmethyloxy acid chloride Green fluorescent protein our -

Iridium(III) corroles phosphoresce with lifetimes ranging from hundreds of nanoseconds to a few microseconds at room temperature, with slightly longer lifetimes at low temperature. DESIG AD SYTESIS F VEL FERRCEE LIKER Introduction Design of the rrocene Linker Results and Discussion Experimental rrocenyl-4-oxobutanoic Acid Propenyl-4-ferrocenyl-4-oxobutanoate rrocenyl-1-hydrazide butanoic Acid Methyl 4-ferrocenyl-4-oxohexanoate rrocenyl-1 hydrazide hexanoic Acid rrocenyl-1,1'-acid Fluoride Methyl ferrocenecarboxylate Methyl-1'-formyl-1-ferrocene carboxylateferrocene ept-6-enylamine rrocenyl-imine-glycine(ethylester), methoxycarbonyl rrocene-methylglycine-ethyl ester, methoxycarbonyl rrocene-1-carboxylic acid-1`carboxaldehyde rrocene carboxaldehyde Resin rrocenyl heptenoic amine Resin Agni[(KLAKKLA) 2 ] (2.24)using ferrocenyl heptenoic amine Resin rrocene carboxaldehyde-polystyrene Resin Allyl-amino ferrocenyl polystyrene Resin Allyl-amino fmoc-phenylalanine ferrocenyl polystyrene Resin...59 iv Cleavage of (1-allylcarbamoyl-2-phenyl-ethyl)-carbamic acid 9-fluoren-9-ylmethyl ester from allyl-amino ferrocenyl polystyrene Resin...60 CAPTER 3. ACID LABILE LIKERS FR SLID PASE SYTESIS F PEPTIDES Introduction Literature Review...7 CAPTER 2.Second, because of easy separation of reagents and products, solid-phase chemistry can be automated more easily than solution 1 chemistry.Separation of compounds bound to the solid support from those in solution is accomplished by simple filtration (figure 1.2).These compounds can be oxidized in the presence of an ammonia source to form novel six-coordinate iridium(III) azaporphyrins in an unprecedented chemical transformation.The characterization and properties of these iridium azaporphyrin complexes are detailed as well, with a focus on nuclear magnetic resonance characterization techniques and a discussion of the red phosphorescence of the azaporphyrins.ne method which imparts flexibility to the cleavage process is to attach a molecule (linker or handle, figure 1.1) to the solid support which facilitates the cleavage of the peptide.Linker Peptide Cleavage Peptide Linker Solid Support Figure 1.1 Schematic representation of a peptide synthesis on solid phase.Solid phase chemistry is currently not as developed as solution-phase chemistry, particularly with regard to small organic molecules, but it has some advantages over the solution-phase.First, in solid-phase synthesis, large excesses of reagents can be used to drive reactions to completion; these excess reagents can then be removed at the end of these reactions by filtration and washing.