Stereoselective synthesis of a-glycosyl thiols by photoinitiated thiol-ene addition

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dc.contributor.advisorBorbás, Anikó
dc.contributor.authorHegazy, Reem
dc.contributor.departmentDE--Természettudományi és Technológiai Kar--Kémiai Intézethu_HU
dc.date.accessioned2021-11-16T12:19:37Z
dc.date.available2021-11-16T12:19:37Z
dc.date.created2021-11-15
dc.description.abstractThe photoinitiated thiol-ene coupling reactions of 2-substituted glycals had previously been discovered to be a relevant method for stereoselective 1,2-cis-a-thioconjugation preparation. Although all glycals reacted with complete a-selectivity, the reactions’ efficiency varied widely. In our study, we tested the response of thiol-ene addition reaction using thioacetic acid under a variety of conditions. different glycals with different configurations and substituents had been used. Different irradiation methods were also investigated. The study revealed that the enantiomers react identically with thioacetic acid since there are no chiral components in our reaction. By using diastereoisomers, we could conclude that the reaction of galacto-configured sugar with thioacetic acid is more beneficial than that of the gluco-configured one. The electron-withdrawing substituents decrease the electron density of the double bond which affects the yield negatively. We also found out that the initiator is being consumed, so irradiating the mixture many times while freshly adding the initiator again is the most efficient way to ensure the continuity of the chain reaction. By exploiting these findings, a series of thioglycoside derivatives can be prepared with high yield and complete stereoselectivity, leading to utilize these carbohydrate memetics more in the pharmaceutical industry.hu_HU
dc.description.correctorhbk
dc.description.courseBiochemical Engineeringhu_HU
dc.description.degreeBSc/BAhu_HU
dc.format.extent31hu_HU
dc.identifier.urihttp://hdl.handle.net/2437/324730
dc.language.isoenhu_HU
dc.subjecta-glycosyl thiolshu_HU
dc.subjectthiol-ene addition reactionhu_HU
dc.subject2-substituted glycalshu_HU
dc.subject.dspaceDEENK Témalista::Kémiahu_HU
dc.titleStereoselective synthesis of a-glycosyl thiols by photoinitiated thiol-ene additionhu_HU
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