Sinteza ferocenskih konjugata D-glukoze i N-acetil-D-glukozamina

master's thesis

• Title (english): Synthesis of ferrocene conjugates of D-glucose and N-acetyl-D-glucosamine
• Author: Franko Pahović
• Mentor: Đani Škalamera (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Biserka Prugovečki (član povjerenstva)
• Committee member: Vesna Petrović Peroković (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2023-12-20, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom diplomskom radu provedena je sinteza D-glukoznih mono- i bis-konjugata ferocena, odnosno N-acetil-D-glukozaminskog mono-konjugata ferocena. Da bi se osigurala konformacijska fleksibilnost te samim time i stvaranje jakih vodikovih veza među ugljikohidratnim prstenovima, planirana je etilenska poveznica između ferocena i šećernih dijelova molekule. Kod monosupstituiranih derivata nije moguća indukcija helikalne kiralnosti ferocena, s obzirom na to da je na samo jedan njegov prsten vezana šećerna jedinica, uslijed čega ovi derivati zapravo služe samo za usporedbu. Očekuje se da će u disupstituirani derivatima, sa šećernim jedinicama vezanim na gornji i donji prsten ferocena, doći do ostvarivanja intramolekulskih vodikovih veza, što bi zbog kiralnosti šećera trebalo inducirati helikalnu kiralnost ferocena. Sinteza D-glukoznih derivata provedena je izravnom metodom glikozilacije peracetilirane D-glukoze uz 2-brometanol kao akceptor glikozidne veze, a u slučaju N-acetil- D-glukozaminskog derivata sinteza je provedena glikozilacijom oksazolinskog međuprodukta 2-brometanolom. Nastali bromidi supstituirani su azidom koji je zatim redukcijom preveden u amin u svrhu kondenzacije s ferocenskom (di)karboksilnom kiselinom. Karakterizacija produkata provedena je uporabom spektroskopskih metoda (IR, NMR).

Abstract (english)

In this diploma thesis, the synthesis of D-glucose mono- and bis-conjugates of ferrocene was carried out, and also an N-acetyl-D-glucosamine mono-conjugate of ferrocene. To ensure conformational flexibility and thus the formation of strong hydrogen bonds between the carbohydrate rings, an ethylene link was planned between ferrocene and the sugar parts of the molecule. In the case of monosubstituted derivatives, the induction of helical chirality of ferrocene is not possible, given that only one of its rings has a sugar unit attached, thus these derivatives serve only for comparison. It is expected that in disubstituted derivatives, with sugar units attached to the both rings of ferrocene, intramolecular hydrogen bonds will form, which should induce helical chirality of ferrocene due to the chirality of the sugar. The synthesis of D-glucose derivatives was carried via direct glycosylation of peracetylated D-glucose with 2-bromoethanol as a glycosidic bond acceptor, and in the case of the N-acetyl-D-glucosamine derivative, the synthesis was performed by glycosylation of the oxazoline intermediate with 2-bromometalnol. The resulting bromides were substituted with an azide, which was then reduced to the amine for the purpose of condensation with ferrocene (di)carboxylic acid. Product characterization was carried out using spectroscopic methods (IR, NMR).

• Keywords: enantioselektivna kataliza; ferocenski peptidi; glikozilacija; helikalna kiralnost
• Keywords (english): enantioselective catalysis; ferrocene peptides; glycosylation; helical chirality
• Language: croatian
• URN:NBN: urn:nbn:hr:217:015937
• Study programme: Title: Graduate university studies in chemistry; specializations in: Graduate university studies in chemistry; Course: Graduate university studies in chemistry; Study programme type: university; Study level: graduate; Academic / professional title: sveučilišni/a magistar/magistra kemije (sveučilišni/a magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-12-20
• Created on: 2024-01-11 13:50:33