Strukturna svojstva potpuno zaštićene muraminske kiseline

undergraduate thesis

• Title (english): The structural properties of novel fully protected muramic acid
• Author: Tanita Petričević
• Mentor: Lidija Barišić (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: 2013-07-10, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Food Technology

Abstract

U ovom su radu opisana strukturna svojstva potpuno zaštićene muraminske kiseline 1(N-Boc-Mur-OMe, Mur = muraminska kiselina) izvedene iz komercijalno dostupnog N-acetilglukozamina. Ugljikohidratna aminokiselina 1 podvrgnuta je strukturnoj analizi primjenom IR- i 1H NMR-spektroskopiju cilju utvrđivanja njezinih konformacijskih svojstava. Spektroskopski podaci dobiveni za Boc-zaštićenu muraminsku kiselinu 1 uspoređeni su s odgovarajućim eksperimentalnim vrijednostima ranije opisanog Ac-zaštićenog analoga 2 da bi se ispitalo utječe li zamjena zaštitne skupine na konformacijska svojstva muraminske kiseline. Pri tomu se pokazalo da uvođenjem glomazne karbamatne zaštitne skupine (Boc) umjesto sterički manje zahtjevne acetamidne skupine (Ac) obrazac intramolekulskih vodikovih veza ostaje očuvan.

Abstract (english)

This final work describes the structural properties of novel fully protected muramic acid 1 (N-Boc-Mur-OMe, Mur = muramic acid) prepared from commercially available N-acetylglycosamine. Novel sugar amino acid 1 was conducted to IR and NMR spectroscopic analysis in order to improve its conformational properties. The spectroscopic data obtained for novel Boc-protected 1 were compared with corresponding experimental values of its previously described Ac-protected analogue 2 in order to examine if the replacement of the protecting groups influences the conformational properties. It was shown that intramolecular hydrogen bonding pattern was preserved upon introduction of sterically hindered carbamate protecting group (Boc) instead of sterically less demanding acetamide group (Ac)

• Keywords: muraminska kiselina; zaštitna skupina; konformacijska analiza; intramolekulske vodikove veze
• Keywords (english): muramic acid; protecting group; conformational analysis; intramolecular hydrogen bond
• Language: croatian
• URN:NBN: urn:nbn:hr:159:912603
• Study programme: Title: Food Technology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-05-03 11:15:41