Towards myo-inositol based hydrogelators

In this master’s thesis, the literature part focuses on the structural aspects, properties, and importance of myo-inositol in numerous biological functions. In addition, the potential and challenges of functionalizing myo-inositol and its ability to act as a gelator in low molecular weight gels a...

Full description

Bibliographic Details
Main Author: Orava, Sarita
Other Authors: Faculty of Sciences, Matemaattis-luonnontieteellinen tiedekunta, Department of Chemistry, Kemian laitos, University of Jyväskylä, Jyväskylän yliopisto
Format: Master's thesis
Language:eng
Published: 2024
Subjects:
Online Access: https://jyx.jyu.fi/handle/123456789/94776
_version_ 1826225769816260608
author Orava, Sarita
author2 Faculty of Sciences Matemaattis-luonnontieteellinen tiedekunta Department of Chemistry Kemian laitos University of Jyväskylä Jyväskylän yliopisto
author_facet Orava, Sarita Faculty of Sciences Matemaattis-luonnontieteellinen tiedekunta Department of Chemistry Kemian laitos University of Jyväskylä Jyväskylän yliopisto Orava, Sarita Faculty of Sciences Matemaattis-luonnontieteellinen tiedekunta Department of Chemistry Kemian laitos University of Jyväskylä Jyväskylän yliopisto
author_sort Orava, Sarita
datasource_str_mv jyx
description In this master’s thesis, the literature part focuses on the structural aspects, properties, and importance of myo-inositol in numerous biological functions. In addition, the potential and challenges of functionalizing myo-inositol and its ability to act as a gelator in low molecular weight gels are discussed. The aim of the experimental part was to prepare myo-inositol based amphiphilic low molecular weight gelators and investigate their gelling properties in biocompatible gels. The myo-inositol based derivatives designed in this work were 2-O-benzyl-myo-inositol and 2-O-Fmoc-myo inositol. The functionalizations were carried out according to a three-step retrosynthesis plan: regio- and stereoselective protection of myo-inositol, regioselective functionalization with the selected target molecule, and removal of the protecting groups. Benzylated myo-inositol derivative was successfully synthesized, and the reaction conditions of this reaction were optimized. Functionalization with Fmoc-moiety was performed under two different reaction conditions, but the desired Fmoc derivative could not be synthesized. In gelation experiments for benzylated myo-inositol, flake formation and partial gel were observed by increasing the concentration. Based on this result, some amphiphilic myo-inositol derivatives may have the potential to act as a gelator in biocompatible gels, but further studies are required to confirm this hypothesis. Tämän Pro gradu -tutkielman kirjallisessa osassa keskitytään myo-inositolin rakenteeseen, ominaisuuksiin ja siihen, mikä tekee myo-inositolista merkityksellisen yhdisteen biologisissa ympäristöissä. Lisäksi tarkastellaan myo-inositolin funktionalisoinnin mahdollisuuksia ja haasteita sekä sen kykyä toimia gelaattorina alhaisen molekyylipainon geeleissä. Tutkielman kokeellisessa osassa tavoitteena oli valmistaa myo-inositolipohjaisia amfifiilisiä alhaisen molekyylipainon gelaattoreita ja tutkia niiden geeliytymisominaisuuksia bioyhteensopivissa geeleissä. Työn suunnitellut johdannaiset olivat 2-O-bentsyyli-myo inositoli ja 2-O-Fmoc-myo-inositoli. Funktionalisoinnit toteutettiin kolmivaiheisen retrosynteesisuunnitelman mukaisesti: myo-inositolin paikka- ja stereoselektiivinen suojaus, paikkaselektiivinen funktionalisointi valitulla kohdemolekyylillä ja suojausryhmien poisto. Työssä onnistuttiin syntetisoimaan bentsyloitua myo-inositolin johdannaista ja optimoimaan kyseisen reaktion reaktio-olosuhteita. Funktionalisointi Fmoc-osan kanssa suoritettiin kahdessa eri reaktio-olosuhteessa, mutta haluttua Fmoc-johdannaista ei onnistuttu syntetisoimaan. Bentsyloidulle myo-inositolille suoritetuissa geeliytymistesteissä havaittiin hiutaleiden muodostumista ja pitoisuutta kasvattamalla osittaista geelin muodostumista. Tämän tuloksen perusteella joillakin myo-inositolin amfifiilisillä johdannaisilla voisi olla potentiaalia toimia gelaattorina bioyhteensopivissa geeleissä, mutta hypoteesin vahvistamiseksi lisätutkimukset ovat välttämättömiä.
first_indexed 2024-05-13T20:00:45Z
format Pro gradu
free_online_boolean 1
fullrecord [{"key": "dc.contributor.advisor", "value": "Nissinen, Maija", "language": null, "element": "contributor", "qualifier": "advisor", "schema": "dc"}, {"key": "dc.contributor.advisor", "value": "Sitsanidis, Efstratios", "language": null, "element": "contributor", "qualifier": "advisor", "schema": "dc"}, {"key": "dc.contributor.author", "value": "Orava, Sarita", "language": "", "element": "contributor", "qualifier": "author", "schema": "dc"}, {"key": "dc.date.accessioned", "value": "2024-05-13T05:00:01Z", "language": null, "element": "date", "qualifier": "accessioned", "schema": "dc"}, {"key": "dc.date.available", "value": "2024-05-13T05:00:01Z", "language": null, "element": "date", "qualifier": "available", "schema": "dc"}, {"key": "dc.date.issued", "value": "2024", "language": null, "element": "date", "qualifier": "issued", "schema": "dc"}, {"key": "dc.identifier.uri", "value": "https://jyx.jyu.fi/handle/123456789/94776", "language": null, "element": "identifier", "qualifier": "uri", "schema": "dc"}, {"key": "dc.description.abstract", "value": "In this master\u2019s thesis, the literature part focuses on the structural aspects, properties, and \nimportance of myo-inositol in numerous biological functions. In addition, the potential and \nchallenges of functionalizing myo-inositol and its ability to act as a gelator in low molecular \nweight gels are discussed. \nThe aim of the experimental part was to prepare myo-inositol based amphiphilic low molecular \nweight gelators and investigate their gelling properties in biocompatible gels. The myo-inositol \nbased derivatives designed in this work were 2-O-benzyl-myo-inositol and 2-O-Fmoc-myo\ninositol. The functionalizations were carried out according to a three-step retrosynthesis plan: \nregio- and stereoselective protection of myo-inositol, regioselective functionalization with the \nselected target molecule, and removal of the protecting groups. Benzylated myo-inositol \nderivative was successfully synthesized, and the reaction conditions of this reaction were \noptimized. Functionalization with Fmoc-moiety was performed under two different reaction \nconditions, but the desired Fmoc derivative could not be synthesized. \nIn gelation experiments for benzylated myo-inositol, flake formation and partial gel were \nobserved by increasing the concentration. Based on this result, some amphiphilic myo-inositol \nderivatives may have the potential to act as a gelator in biocompatible gels, but further studies \nare required to confirm this hypothesis.", "language": "en", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.abstract", "value": "T\u00e4m\u00e4n Pro gradu -tutkielman kirjallisessa osassa keskityt\u00e4\u00e4n myo-inositolin rakenteeseen, \nominaisuuksiin ja siihen, mik\u00e4 tekee myo-inositolista merkityksellisen yhdisteen biologisissa \nymp\u00e4rist\u00f6iss\u00e4. Lis\u00e4ksi tarkastellaan myo-inositolin funktionalisoinnin mahdollisuuksia ja \nhaasteita sek\u00e4 sen kyky\u00e4 toimia gelaattorina alhaisen molekyylipainon geeleiss\u00e4. \nTutkielman kokeellisessa osassa tavoitteena oli valmistaa myo-inositolipohjaisia amfifiilisi\u00e4 \nalhaisen \nmolekyylipainon gelaattoreita ja tutkia niiden geeliytymisominaisuuksia \nbioyhteensopivissa geeleiss\u00e4. Ty\u00f6n suunnitellut johdannaiset olivat 2-O-bentsyyli-myo\ninositoli \nja \n2-O-Fmoc-myo-inositoli. Funktionalisoinnit toteutettiin kolmivaiheisen \nretrosynteesisuunnitelman mukaisesti: myo-inositolin paikka- ja stereoselektiivinen suojaus, \npaikkaselektiivinen funktionalisointi valitulla kohdemolekyylill\u00e4 ja suojausryhmien poisto. \nTy\u00f6ss\u00e4 onnistuttiin syntetisoimaan bentsyloitua myo-inositolin johdannaista ja optimoimaan \nkyseisen reaktion reaktio-olosuhteita. Funktionalisointi Fmoc-osan kanssa suoritettiin kahdessa \neri reaktio-olosuhteessa, mutta haluttua Fmoc-johdannaista ei onnistuttu syntetisoimaan. \nBentsyloidulle myo-inositolille suoritetuissa geeliytymistesteiss\u00e4 havaittiin hiutaleiden \nmuodostumista ja pitoisuutta kasvattamalla osittaista geelin muodostumista. T\u00e4m\u00e4n tuloksen \nperusteella joillakin myo-inositolin amfifiilisill\u00e4 johdannaisilla voisi olla potentiaalia toimia \ngelaattorina bioyhteensopivissa geeleiss\u00e4, mutta hypoteesin vahvistamiseksi lis\u00e4tutkimukset \novat v\u00e4ltt\u00e4m\u00e4tt\u00f6mi\u00e4.", "language": "fi", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Submitted by Paivi Vuorio (paelvuor@jyu.fi) on 2024-05-13T05:00:01Z\nNo. of bitstreams: 0", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Made available in DSpace on 2024-05-13T05:00:01Z (GMT). No. of bitstreams: 0\n Previous issue date: 2024", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.format.extent", "value": "104", "language": "", "element": "format", "qualifier": "extent", "schema": "dc"}, {"key": "dc.language.iso", "value": "eng", "language": null, "element": "language", "qualifier": "iso", "schema": "dc"}, {"key": "dc.rights", "value": "In Copyright", "language": "en", "element": "rights", "qualifier": null, "schema": "dc"}, {"key": "dc.subject.other", "value": "myo-inositol", "language": "", "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.subject.other", "value": "myo-inositol derivatives", "language": "", "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.subject.other", "value": "phosphorylated myo-inositols", "language": "", "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.subject.other", "value": "biocompatible gels", "language": "", "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.subject.other", "value": "myo-inositoli", "language": "", "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.title", "value": "Towards myo-inositol based hydrogelators", "language": "", "element": "title", "qualifier": null, "schema": "dc"}, {"key": "dc.type", "value": "master thesis", "language": null, "element": "type", "qualifier": null, "schema": "dc"}, {"key": "dc.identifier.urn", "value": "URN:NBN:fi:jyu-202405133547", "language": null, "element": "identifier", "qualifier": "urn", "schema": "dc"}, {"key": "dc.type.ontasot", "value": "Master\u2019s thesis", "language": "en", "element": "type", "qualifier": "ontasot", "schema": "dc"}, {"key": "dc.type.ontasot", "value": "Pro gradu -tutkielma", "language": "fi", "element": "type", "qualifier": "ontasot", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Faculty of Sciences", "language": "en", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Matemaattis-luonnontieteellinen tiedekunta", "language": "fi", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Department of Chemistry", "language": "en", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Kemian laitos", "language": "fi", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "University of Jyv\u00e4skyl\u00e4", "language": "en", "element": "contributor", "qualifier": "organization", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "Jyv\u00e4skyl\u00e4n yliopisto", "language": "fi", "element": "contributor", "qualifier": "organization", "schema": "dc"}, {"key": "dc.subject.discipline", "value": "Organic Chemistry", "language": "en", "element": "subject", "qualifier": "discipline", "schema": "dc"}, {"key": "dc.subject.discipline", "value": "Orgaaninen kemia", "language": "fi", "element": "subject", "qualifier": "discipline", "schema": "dc"}, {"key": "yvv.contractresearch.funding", "value": "0", "language": "", "element": "contractresearch", "qualifier": "funding", "schema": "yvv"}, {"key": "dc.type.coar", "value": "http://purl.org/coar/resource_type/c_bdcc", "language": null, "element": "type", "qualifier": "coar", "schema": "dc"}, {"key": "dc.rights.accesslevel", "value": "openAccess", "language": null, "element": "rights", "qualifier": "accesslevel", "schema": "dc"}, {"key": "dc.type.publication", "value": "masterThesis", "language": null, "element": "type", "qualifier": "publication", "schema": "dc"}, {"key": "dc.subject.oppiainekoodi", "value": "4035", "language": null, "element": "subject", "qualifier": "oppiainekoodi", "schema": "dc"}, {"key": "dc.subject.yso", "value": "orgaaninen kemia", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "geelit", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "hydrogeelit", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "organic chemistry", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "gels", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "hydrogels", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.rights.url", "value": "https://rightsstatements.org/page/InC/1.0/", "language": null, "element": "rights", "qualifier": "url", "schema": "dc"}]
id jyx.123456789_94776
language eng
last_indexed 2025-02-18T10:55:27Z
main_date 2024-01-01T00:00:00Z
main_date_str 2024
online_boolean 1
online_urls_str_mv {"url":"https:\/\/jyx.jyu.fi\/bitstreams\/bae6b4f6-9a48-4bee-8e7b-feb6c5437a3b\/download","text":"URN:NBN:fi:jyu-202405133547.pdf","source":"jyx","mediaType":"application\/pdf"}
publishDate 2024
record_format qdc
source_str_mv jyx
spellingShingle Orava, Sarita Towards myo-inositol based hydrogelators myo-inositol myo-inositol derivatives phosphorylated myo-inositols biocompatible gels myo-inositoli Organic Chemistry Orgaaninen kemia 4035 orgaaninen kemia geelit hydrogeelit organic chemistry gels hydrogels
title Towards myo-inositol based hydrogelators
title_full Towards myo-inositol based hydrogelators
title_fullStr Towards myo-inositol based hydrogelators Towards myo-inositol based hydrogelators
title_full_unstemmed Towards myo-inositol based hydrogelators Towards myo-inositol based hydrogelators
title_short Towards myo-inositol based hydrogelators
title_sort towards myo inositol based hydrogelators
title_txtP Towards myo-inositol based hydrogelators
topic myo-inositol myo-inositol derivatives phosphorylated myo-inositols biocompatible gels myo-inositoli Organic Chemistry Orgaaninen kemia 4035 orgaaninen kemia geelit hydrogeelit organic chemistry gels hydrogels
topic_facet 4035 Orgaaninen kemia Organic Chemistry biocompatible gels geelit gels hydrogeelit hydrogels myo-inositol myo-inositol derivatives myo-inositoli orgaaninen kemia organic chemistry phosphorylated myo-inositols
url https://jyx.jyu.fi/handle/123456789/94776 http://www.urn.fi/URN:NBN:fi:jyu-202405133547
work_keys_str_mv AT oravasarita towardsmyoinositolbasedhydrogelators