Prikaz osnovnih podataka o disertaciji
Pirolidinski derivati u organokatalitičkim transformacijama
Pyrrolidine derivatives in organocatalytic transformations
dc.contributor.advisor | Savić, Vladimir | |
dc.contributor.other | Tešević, Vele | |
dc.contributor.other | Ferjančić, Zorana | |
dc.contributor.other | Maslak, Veselin | |
dc.contributor.other | Nikodinović-Runić, Jasmina | |
dc.creator | Jovanović, Predrag M. | |
dc.date.accessioned | 2017-06-17T08:53:11Z | |
dc.date.available | 2017-06-17T08:53:11Z | |
dc.date.available | 2020-07-03T10:16:23Z | |
dc.date.issued | 2017-04-07 | |
dc.identifier.uri | http://eteze.bg.ac.rs/application/showtheses?thesesId=5057 | |
dc.identifier.uri | https://nardus.mpn.gov.rs/handle/123456789/8300 | |
dc.identifier.uri | https://fedorabg.bg.ac.rs/fedora/get/o:15788/bdef:Content/download | |
dc.identifier.uri | http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=49041935 | |
dc.description.abstract | Hiralni, polisupstituisani derivati pirolidina, dobijeni cikloadicionim reakcijama azometinskih ilida, proučavani su kao organokatalizatori u Michael-ovoj reakciji aldehida/ketona i vinil-sulfona. Pod optimalnim reakcionim uslovima, u kojima se koristilo 10 mol % katalizatora u vlažnom metilen-hloridu prinosi reakcija su generalno bili dobri dok je enantioselektivnost varirala dostižući 52 %. Razvijen je efikasan biokatalizator za asimetričnu Michael-ovu adiciju acetaldehida na β- nitrostiren na bazi celih ćelija koja eksprimira 4-oksalokrotonat tautomerazu (4-OT). Utvrđen je optimalan odnos supstrata i biokatalizatora. Kada je kao supstrat korišćen β-nitrostiren dobijena je odlična enantioselektivnost (e.e. >99%) uz prinos reakcije do 60%. Biokatalizator je manje efikasan sa p-hlor-, o-hlor- i p-fluor-β-nitrostirenom gde su dobijeni prinosi od 38%, 51%, 31% i e.e. 84%, 88%, 94%... | sr |
dc.description.abstract | Chiral, polysubstituted pirrolydines derivatives, obtained via cycloaddition reactions of azomethine ylides, were studied as organocatalysts in the Michael reaction of aldehydes/ketones and vinylsulphones. Under optimised reaction conditions employing 10 mol % of the catalyst in wet CH2Cl2, the yields of the products were generally good while the enantioselectivity varied, reaching up to 52 %. A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to β-nitrostyrenes. Optimal ratio of substrates and biocatalyst was determined. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with β-nitrostyrene substrate. The biocatalyst exhibited lower reaction rates with pchloro-, o-chloro- and p-fluoro-β-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively... | en |
dc.format | application/pdf | |
dc.language | sr | |
dc.publisher | Универзитет у Београду, Хемијски факултет | sr |
dc.rights | openAccess | en |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Универзитет у Београду | sr |
dc.subject | organokataliza | sr |
dc.subject | organocatalysis | en |
dc.subject | proline derivatives | en |
dc.subject | thiourea derivatives | en |
dc.subject | 4-Oxalocrotonate tautomerase | en |
dc.subject | Michael reaction | en |
dc.subject | enantioselectivity | en |
dc.subject | biocatalysis | en |
dc.subject | Escherichia coli | en |
dc.subject | derivati prolina | sr |
dc.subject | derivati tiouree | sr |
dc.subject | 4-oksalokrotonat tautomeraza | sr |
dc.subject | Michael-ova reakcija | sr |
dc.subject | enantioselektivnost | sr |
dc.subject | biokataliza | sr |
dc.subject | Escherichia coli | sr |
dc.title | Pirolidinski derivati u organokatalitičkim transformacijama | sr |
dc.title.alternative | Pyrrolidine derivatives in organocatalytic transformations | en |
dc.type | doctoralThesis | en |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Савић, Владимир; Ферјанчић, Зорана; Никодиновић-Рунић, Јасмина; Тешевић, Веле; Маслак, Веселин; Јовановић, Предраг М.; Пиролидински деривати у органокаталитичким трансформацијама; Пиролидински деривати у органокаталитичким трансформацијама; | |
dc.identifier.fulltext | https://nardus.mpn.gov.rs/bitstream/id/30386/Disertacija.pdf | |
dc.identifier.fulltext | https://nardus.mpn.gov.rs/bitstream/id/30387/IzvestajKomisije10980.pdf | |
dc.identifier.fulltext | http://nardus.mpn.gov.rs/bitstream/id/30386/Disertacija.pdf | |
dc.identifier.fulltext | http://nardus.mpn.gov.rs/bitstream/id/30387/IzvestajKomisije10980.pdf | |
dc.identifier.rcub | https://hdl.handle.net/21.15107/rcub_nardus_8300 |