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master's thesis
Sinteza i inhibitorni učinak ferocenskih manozida
Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology, 2015. urn:nbn:hr:159:960219
Sučić, Antonija
University of Zagreb
Faculty of Food Technology and Biotechnology
Department of Chemistry and Biochemistry
Laboratory for Organic Chemistry

Institutional repository: Repository of the Faculty of Food Technology and Biotechnology

Cite this document

Sučić, A. (2015). Sinteza i inhibitorni učinak ferocenskih manozida (Master's thesis). Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:159:960219

Sučić, Antonija. "Sinteza i inhibitorni učinak ferocenskih manozida." Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, 2015. https://urn.nsk.hr/urn:nbn:hr:159:960219

Sučić, Antonija. "Sinteza i inhibitorni učinak ferocenskih manozida." Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, 2015. https://urn.nsk.hr/urn:nbn:hr:159:960219

Sučić, A. (2015). 'Sinteza i inhibitorni učinak ferocenskih manozida', Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, accessed 09 September 2024, https://urn.nsk.hr/urn:nbn:hr:159:960219

Sučić A. Sinteza i inhibitorni učinak ferocenskih manozida [Master's thesis]. Zagreb: University of Zagreb, Faculty of Food Technology and Biotechnology; 2015 [cited 2024 September 09] Available at: https://urn.nsk.hr/urn:nbn:hr:159:960219

A. Sučić, "Sinteza i inhibitorni učinak ferocenskih manozida", Master's thesis, University of Zagreb, Faculty of Food Technology and Biotechnology, Zagreb, 2015. Available at: https://urn.nsk.hr/urn:nbn:hr:159:960219

Metadata
TitleSinteza i inhibitorni učinak ferocenskih manozida
Title (english)Synthesis and inhibitory effect of ferrocene mannosides
AuthorAntonija Sučić
MentorVeronika Kovač (mentor)
GranterUniversity of Zagreb
Faculty of Food Technology and Biotechnology
(Department of Chemistry and Biochemistry)
(Laboratory for Organic Chemistry)
Zagreb
Defense date and country2015-09-30, Croatia
Scientific / art field,
discipline and subdiscipline		BIOTECHNICAL SCIENCES
Biotechnology
Abstract
Prema postupcima opisanim u literaturi pripravljene su g-ferocenbutanska kiselina (3, 80%) i d-ferocenpentanska kiselina (4, 74%). Djelovanjem smjese NEt3/ClCOOEt, uz naknadni dodatak NaN3/ H2O, ti su spojevi pretvoreni u odgovarajuće acil-azide 7 (78%) i 8 (75%). Pregradnjom azida 7 i 8 u t-BuOH dobiveni su Boc-zaštićeni amini 9 (75%) i 10 (62%), koji su djelovanjem HCl (g) i kasnijom obradom s NEt3 prevedeni u amine 11 (72%) i 12 (60%). Primjenom HOBt/EDCpostupka kondenziran je manozid 13 s ferocenskim aminima 11 i 12, te su dobivene α, β anomerne smjese amidnih konjugata 14 (58%) i 15 (50%). O-debenziliranjem hidroksilnih skupina α- anomera spojeva 14 i 15 djelovanjem vodika uz Pd-C, pripravljeni su ferocenski manozidi 16 (32%) i 17 (59%), koji su zatim testirani kao inhibitori manoza-specifične adhezije bakterije E. coli na eritrocite zamorčića (test inhibicije hemaglutinacije). Strukture svih sintetiziranih spojeva potvrđene su spektroskopskim metodama (IR, 1H-NMR i 13C-NMR).
Abstract (english)
Following the procedures described in the literature g-ferrocenebutanoic acid (3, 80%) i d- ferrocenepentanoic acid (4, 74%) were prepared. After reacting with the mixture of NEt3/ClCOOEt, and with the addition of NaN3/H2O, these compounds were converted into the corresponding acyl azide 7 (78%) and 8 (75%). By rearranging the azide 7 and 8 in t-BuOH Boc-protected amine 9 (75%) and 10 (62%) were obtained which reacted with HCl (g) and were subsequently treated with NEt3 to be converted to the amines 11 (72%) and 12 (60%). By using the HOBt/EDC procedure, mannoside 13 has been condensed with ferrocene amines 11 and 12 and the α, β anomeric mixtures of amide conjugates 14 (58%) and 15 (50%) were obtained. Ferrocene mannosides 16 (32%) and 17 (59%) were obtained by O-debenzylation of the hydroxyl groups of the compounds 14a and 15a by reacting with hydrogen along with Pd-C. Compounds 16 and 17 were then tested as the inhibitors of the mannosespecific adhesion of the bacteria E.coli to guinea pig erythrocytes (Inhibition Hemagglutination Test). The structures of all the synthesized compounds were confirmed by spectroscopic methods (IR, 1H NMR and 13C NMR).
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:159:960219
Study programmeTitle: Molecular Biotechnology
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra inženjer/inženjerka molekularne biotehnologije (magistar/magistra inženjer/inženjerka molekularne biotehnologije)
Type of resourceText
File originBorn digital
Access conditionsAccess restricted to students and staff of home institution
Terms of useLicence In copyright icon
Created on2017-04-28 09:06:56