Sinteza glukozilnog etera L-tirozil-L-serina

master's thesis

• Title (english): Synthesis of glucopyranosyl ether of L-tyrosyl-L-serine
• Author: Nataša Vlaisavljević
• Mentor: Jasna Vorkapić-Furač (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Biochemical Engineering); (Laboratory for Cell Technology, Application and Biotransformations); Zagreb
• Defense date and country: 2005-10-07, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

O-Glikozidi čine važnu skupinu prirodnih spojeva u kojima je ugljikohidratna komponenta eterskim tipom veze vezana na peptid ili protein. Ovaj tip veze u kojem je D- -glukoza vezana na hidroksilnu skupinu L-tirozina nalazimo u glikogeninu, autokatalitičkom proteinu koji pokreće sintezu glikogena, ali i u glikoproteinskom omotaču bakterija. Cilj ovog diplomskog rada je sinteza N-benziloksikarbonil-O-(2,3,4,6-tetra-O- -benzil-β-D-glukopiranozil)-L-tirozil-L-serin benzilnog estera. Sinteza je provedena na dva načina: vezanjem odgovarajuće zaštićenog L-serina na N-benziloksikarbonil-O-(2,3,4,6- -tetra-O-benzil-β-D-glukopiranozil)-L-tirozin (indirektna metoda) i O-glukoziliranjem N-benziloksikarbonil-L-tirozil-L-serin benzilnog estera (direktna metoda). Produkti su izolirani kromatografijom na stupcu silikagela, te karakterizirani NMR spektroskopijom, elementnom analizom, talištem i optičkim skretanjem.

Abstract (english)

O-Glycosides in which the carbohydrate moiety is through ether type of linkage attached to a peptide or a protein, are the part of an important group of natural compounds. This type of linkage in which D-glucose is bound to the hydroxyl group of L-tyrosine, is found in glycogenin, the protein primer for glycogen synthesis, as also in the surface-layer glycoprotein of bacteria. The aim of this work was the synthesis of N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O- -benzyl-β-D-glucopyranosyl)-L-tyrosyl-L-serine benzyl ester. Two different ways for the synthesis were examined: coupling of properly protected L-serine with N-benzyloxycarbonyl- -O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-tyrosine (indirect method) and by O-glucosylation of N-benzyloxycarbonyl-L-tyrosyl-L-serine benzyl ester (direct method). All compounds prepared were characterized by NMR spectroscopy, elemental analysis, melting point and optical rotation.

• Keywords: O-glukokonjugati; peptidna sinteza
• Keywords (english): O-glucoconjugates; peptide synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:323589
• Study programme: Title: Biotechnology; specializations in: Biochemical Engineering; Course: Biochemical Engineering; Study programme type: university; Study level: graduate; Academic / professional title: diplomirani inženjer biotehnologije; smjer biokemijsko inženjerstvo (diplomirani inženjer biotehnologije; smjer biokemijsko inženjerstvo)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Access restricted to students and staff of home institution
• Created on: 2017-09-11 09:58:46