Derivatizacija flavonoida kvercetina s biološki aktivnim peptidom Leu-enkefalinom

master's thesis

• Title (english): Derivation of flavonoid quercetin with biologically active peptide Leu-enkephalin
• Author: Jelena Batinić
• 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: 2009-12-04, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Ovaj diplomski rad obuhvaća derivatizaciju flavonoida kvercetina s endogenim opioidnim peptidom Leu-enkefalinom. Zaštićeni Leu-enkefalin potreban u sintezi priređen je u dva stupnja. U prvom stupnju iz Z-Tyr(Bzl)-OH i H-Gly-Gly-OH sintetiziran je tripeptid Z-Tyr(Bzl)-Gly-Gly-OH (1), a zatim u drugom stupnju produženjem peptidnog lanca s H-Phe-Leu-OH dobiven je pentapeptid ZTyr( Bzl)-Gly-Gly-Phe-Leu-OH (2). Reakcija između kvercetina i zaštićenog pentapeptida 2 daje 2-{3-hidroksi-4- [benziloksikarbonil-L-tirozil(benzil)glicilglicil-L-fenilalanil-L-leucil]fenil}-3,5,7-trihidroksi- 4H-1-benzopiran-4-on (3) iz kojeg u reakciji skidanja zaštite pored očekivanog nezaštićenog produkta 2-[3-hidroksi-4-(L-tirozilglicilglicil-L-fenilalanil-L-leucil)fenil]-3,5,7-trihidroksi-4H- 1-benzopiran-4-ona (4) nastaje i produkt transesterifikacije 2-[3-L-tirozilglicilglicil-Lfenilalanil- L-leucil)-4-hidroksifenil]-3,5,7-trihidroksi-4H-1-benzopiran-4-on (5).

Abstract (english)

This graduate thesis includes derivation of flavonoid quercetin with endogenous opioid peptide Leu-enkephalin. Protected Leu-enkephalin required in the synthesis was prepared in two stages. In the first stage from Z-Tyr(Bzl)-OH and H-Gly-Gly-OH tripeptide Z-Tyr(Bzl)-Gly-Gly-OH (1) was synthesized and then in the second stage peptide chain was elongated with H -Phe-Leu-OH to obtaine pentapeptide Z-Tyr(Bzl)-Gly-Gly-Phe-Leu-OH (2). Reaction between quercetin and protected pentapeptide 2 gave 2-{3-hydroxy-4- [benzyloxycarbonyl-L-tyrosyl(benzyl)glycylglycyl-L-fenylalanyl-L-leucyl]phenyl)-3,5,7- trihydroxy-4H-1-benzopyran-4-on (3) which after the reaction of deprotection gave deprotected product 2-[3-hydroxy-4-(L-tyrosylglycylglycyl-L-fenylalanyl-L-leucyl) phenyl]- 3,5,7-trihydroxy-4H-1-benzopyran-4-on (4) and 2-[3-(L-tyrosylglycylglycyl-L-fenylalanyl-Lleucyl)- 4-hydroxyfenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-on (5) as a product of transesterification.

• Keywords: flavonoidi; kvercetin; Leu-enkefalin; peptidi
• Keywords (english): flavonoids; quercetin; Leu-enkephalin; peptide
• Language: croatian
• URN:NBN: urn:nbn:hr:159:792552
• 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: 2017-09-01 08:45:24