Sinteza i inhibitorni učinak ferocenskih manozida

master's thesis

• Title (english): Synthesis and inhibitory effect of ferrocene mannosides
• Author: Antonija Sučić
• Mentor: Veronika Kovač (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2015-09-30, 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: ferocen; manoza; E.coli; fimbrije tipa 1; hemaglutinacija
• Keywords (english): ferrocene; mannose; E.coli; type 1 fimbriae; hemagglutination
• Language: croatian
• URN:NBN: urn:nbn:hr:159:960219
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-04-28 09:06:56