Reaktivnost amino-skupina lizina u Maillardovoj reakciji

master's thesis

• Title (english): Reactivity of the amino groups of lysine in the Maillard reaction
• Author: Danijela Mikulčić
• 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: 2006-06-05, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

U okviru ovog diplomskog rada sintetiziran je i okarakteriziran pentapeptid aminokiselinskog slijeda H-Lys-Gly-Gly-Phe-Leu-OH (5). Proučavana je reakcija neenzimske glikacije peptida 5 s Dglukozom kao šećernom komponentom. Istraživanja su obuhvatila ispitivanje reaktivnosti Nα- i Nε- amino-skupina lizinskog ostatka u metanolu kao otapalu pri različitim koncentracijama monosaharidne komponente te izolaciju i karakterizaciju produkata uz uporabu metoda koje uključuju primjenu tekućinske kromatografije i NMR spektroskopije. Ustanovljeno je da reakcija slobodnih amino-skupina peptida 5 s karbonilnom skupinom aldoheksoze rezultira nastajanjem Amadorijevih spojeva Nα-(1-deoksi-D-fruktoz-1-il)-L-lizilglicilglicil- L-fenilalanil-L-leucina (6), Nε-(1-deoksi-D-fruktoz-1-il)-L-lizil-glicilglicil-L-fenilalanil-L-leucina (7) i Nα,Nε-di-(1-deoksi-D-fruktoz-1-il)-L-lizil-glicilglicil-L-fenilalanil-L-leucina (8).

Abstract (english)

As a part of this Graduated paper, pentapeptide H-Lys-Gly-Gly-Phe-Leu-OH (5) has been synthesized and characterized. Nonenzymatic glycation reaction of peptide 5 with D-glucose as a sugar moiety has been studied. The research was focused on the examination of the reactivity of Nα- and Nε-amino groups of lysyl residue in methanol as a solvent in the presence of different concentrations of carbohydrate moiety. The structure and distribution of the generated products were assessed by RP HPLC method as well as by NMR spectroscopy. It was demonstrated that reaction of the free amino groups of peptide 5 with the carbonyl group of the aldohexose results in the formation of Amadori compounds Nα-(1-deoxy-D-fructos-1- yl)-L-lysyl-glycylglycyl-L-phenylalanyl-L-leucine (6), Nε-(1-deoxy-D-fructos-1-yl)-L-lysyl-glycylglycyl-Lphenylalanyl- L-leucine (7) and Nα,Nε-di-(1-deoxy-D-fructos-1-yl)-L-lysyl-glycylglycyl-L-phenylalanyl- L-leucine (8).

• Keywords: Amadorijev spoj; Maillardova reakcija; neenzimska glikacija; lizin; D-glukoza
• Keywords (english): Amadori compound; Maillard reaction; nonenzymatic glycation; lysine; D-glucose
• Language: croatian
• URN:NBN: urn:nbn:hr:159:063403
• 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: 2017-09-07 11:10:22