?url_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rft.relation=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F32913%2F&rft.title=Total+Synthesis+of+Tubiashinol&rft.creator=Sigindere%2C+Cihad&rft.description=The+genus+Vibrio+harbors+over+100+species+and+some+of+them+are+well-known+(e.g.+Vibrio+anguillarum+and+Vibrio+cholerae.)+They+are+Gram-negative+and+comma-shaped+bacteria+which+are+present+within+many+diverse+marine+organisms+and+habitats%2C+such+as+mollusks%2C+shrimps%2C+fishes%2C+and+corals.+They+have+an+array+of+extracellular+products+some+of+which+cause+toxicity.%0D%0AAnother+species%2C+Vibrio+tubiashii%2C+is+found+in+Pacific+Ocean+and+has+shown+to+be+a+prevalent+pathogen+of+oyster+larvae.+It+increasingly+affects+oyster+populations+as+well+as+being+a+problem+for+oyster+hatcheries%2C+nurseries+and+farms.+With+implementing+genome+mining%2C+our+group+has+identified+a+gene+cluster+which+is+responsible+for+a+bio-pathway+of+couple+metabolites.+Isolated+and+characterized+authentic+samples+were+used+in+a+collaborative+study+and+one+of+the+metabolites+showed+toxicity+towards+oyster+larvae+and+zebra+fish+embryo.+After+this+observation%2C+we+become+interested+in+the+synthesis+of+this+toxic+marine+natural+product+and+named+it+tubiashinol.%0D%0AThe+coupling+of+the+first+2+building+blocks+was+achieved+after+testing+few+different+agents+and+the+diastereomerically+pure+dipeptide+(N-terminus)+was+obtained.+However%2C+synthesis+of+(3R%2C4S)-4-amino-6-methylheptane-1%2C3-diol+(C-terminal)+was+challenging+and+we+had+to+try+number+of+strategies+to+attain+the+desired+amino-diol.+In+the+process%2C+we+also+obtained+the+3-epi+diastereomer+and+the+absolute+stereochemistry+of+its+precursor+was+determined+by+X-Ray+which+fortified+our+characterizations.+This+diastereomer+was%2C+then%2C+used+to+synthesize+3-epi+tubiashinol+which+was+compared+to+tubiashinol+later.%0D%0AIn+this+study%2C+we+reported+the+first+Vibrio+tubiashii+metabolite+which+is+toxic+to+oyster+larvae.+We+successfully+synthesized+and+characterized+tubiashinol+and+3-epi+tubiashinol+and+compared+them+to+determine+the+absolute+stereochemistry+of+tubiashinol+in+proton+(1H)+NMR+studies.&rft.date=2017-09-21&rft.type=University+of+Pittsburgh+ETD&rft.type=PeerReviewed&rft.format=application%2Fpdf&rft.language=en&rft.identifier=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F32913%2F1%2FDoc%2520v9%252C%2520Total%2520Syn%2520of%2520Tubiashinol%2520-%2520Sigindere%2520C.pdf&rft.identifier=++Sigindere%2C+Cihad++(2017)+Total+Synthesis+of+Tubiashinol.++Master's+Thesis%2C+University+of+Pittsburgh.++++(Unpublished)++