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dc.contributor.authorMaitrani, Chandan Laxman
dc.date.accessioned2014-03-04T18:19:49Z
dc.date.available2014-03-04T18:19:49Z
dc.date.issued2009-08
dc.identifier.othermaitrani_chandan_l_200908_phd
dc.identifier.urihttp://purl.galileo.usg.edu/uga_etd/maitrani_chandan_l_200908_phd
dc.identifier.urihttp://hdl.handle.net/10724/25877
dc.description.abstractThe present dissertation includes five chapters: Chapter 1 includes the introduction to tryptophan and the enzyme kynureninase, along with literature review Chapter 2 includes the synthesis of the various substrate analogs of the enzyme kynureninase. A detailed synthetic method for the preparation of the racemic 3-chloro, 3-fluoro, 3-methyl, 5-bromo, and 5-chloro kynurenines has been described in this chapter. The racemic 3-chloro, 3-fluoro, and 3-methyl kynurenines have been prepared starting from the corresponding o-substituted anilines. A diazotization of these anilines followed by a stannous chloride reduction gives the corresponding 2-substituted phenylhydrazines. Reaction of the phenylhydrazines with the Michael adduct of diethyl acetamidomalonate and acrolein give the corresponding 2-substituted phenylhydrazone derivatives. These phenylhydrazone derivatives are then subjected to a Fischer indole cyclization to give the 3,7-disubstituted indoles. Ozonolysis of the indoles followed by acid hydrolysis affords the racemic kynurenines. The 5-bromo-L-kynurenine and 5-chloro-L-kynurenine have been prepared from L-tryptophan. Chapter 3 includes the results and discussion of the steady state kinetic studies of the synthesized substrate analogs Chapter 4 includes the synthesis of a caged kynurenines and its stability studies using HPLC Chapter 5 includes Conclusions
dc.languageeng
dc.publisheruga
dc.rightspublic
dc.subjectKynureninase, Pseudomonas fluorescens, kynurenine, enzymatic resolution, Aspergillus acylase, substituted phenylhydrazine, substituted phenyl- hydrazones, Fischer indole cylization, ozonolysis, hydrolysis
dc.titleSynthesis & evaluation of substrate analogs for human & bacterial kynureninase and synthesis and stability studies of caged kynurenine
dc.typeDissertation
dc.description.degreePhD
dc.description.departmentChemistry
dc.description.majorChemistry
dc.description.advisorRobert Phillips
dc.description.committeeRobert Phillips
dc.description.committeeGeorge Majetich
dc.description.committeeJonathan Amster


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