Sinteza N-glukodipeptida aminokiselinske sekvencije L-Trp-L-Phe

master's thesis

• Title (english): Synthesis of N-glucodipeptides with amino acid sequence L-Trp-L-Phe
• Author: Antonija Trontel
• 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: 2006-12-01, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

S ciljem dobivanja modelnih spojeva, a u svrhu ispitivanja neenzimskih reakcija za koje se pretpostavlja da se odvijaju in vivo, sintetizirani su 2-(N-tert-butiloksikarbonil-L-triptofanil-L-fenilalanilamido)-2-deoksi-D-glukopiranoza 11 i 6-(N-tert-butiloksikarbonil-L-triptofanil-L-fenilalanilamido)-6-deoksi-D-glukopiranoza 14. Sinteza polazi od priprave 2-(N-tert-butiloksikarbonil-L-fenilalanilamido)-2-deoksi-D-glukopiranoze 8 i 6-(N-tert-butiloksikarbonil-L-fenilalanilamido)-6-deoksi-D-glukopiranoze 12 i to kondenzacijom N-tert-butiloksikarbonil-L-fenilalanina 6 sa 2-amino-2-deoksi- 7, odnosno 6-amino-6-deoksi-D-glukopiranozom 4 (metodama mješovitog anhidrida i aktivnog estera). Deprotekcijom produkata 8 i 12, te kondenzacijom sa N-sukcinimidnim esterom N-tert-butiloksikarbonil-L-triptofana 10 dobiveni su N-glukokonjugati 11 i 14. Produkti su izolirani kromatografijom na stupcu silikagela, te karakterizirani NMR spektroskopijom, elementnom analizom, talištem i optičkim skretanjem.

Abstract (english)

In order to obtain the model compounds for the study of non-enzymatic reactions which are supposed to take place in vivo, 2-(N-tert-butyloxycarbonyl-L-tryptophanyl-L-phenylalanylamido)-2-deoxy-D-glucopyranose 11 and 6-(N-tert-butyloxycarbonyl-L-tryptophanyl-L-phenylalanylamido)-6-deoxy-D-glucopyranose 14 were synthesized. The synthesis started with the preparation of 2-(N-tert-butyloxycarbonyl-L-phenylalanylamido)-2-deoxy-D-glucopyranose 8 and 6-(N-tert-butyloxycarbonyl-L-phenylalanylamido)-6-deoxy-D-glucopyranose 12 by the reaction of N-tert-butyloxycarbonyl-L-phenylalanine 6 with 2-amino-2-deoxy- 7 and 6-amino-6-deoxy-D-glucopyranose 4, respectively (through the mixed anhydride and active ester methods). Deprotection of the products 8 and 12, following with the condensation with N-succinimide ester of N-tert-butyloxycarbonyl-L-tryptophane 10 gave N-glucoconjugates 11 and 14. All compounds prepared were characterized by NMR spectroscopy, elemental analysis, melting point and optical rotation.

• Keywords: aminošećeri; endomorfin; N-glikokonjugati
• Keywords (english): aminosugars; endomorphin; N-glycoconjugates
• Language: croatian
• URN:NBN: urn:nbn:hr:159:041447
• 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: 2017-09-08 08:04:32