{"id":{"repo_id":"qu-belfast","oai_identifier":"oai:pure.qub.ac.uk/portal:studenttheses/699b19b0-6576-4d48-9592-93ba3c636bd4"},"canonical_url":"https://search.dev.ndltd.org/etd/qu-belfast/oai:pure.qub.ac.uk/portal:studenttheses/699b19b0-6576-4d48-9592-93ba3c636bd4","repository":{"repo_id":"qu-belfast","name":"Queen's University Belfast","base_url":"https://pureadmin.qub.ac.uk/ws/oai"},"display":{"title":"Synthetic efforts towards the total synthesis of the Nucleoside Antibiotic, (+)-Amicetin","abstract":"(+)-Amicetin is a hexopyranosyl cytosine, a relatively unexplored class of RNA-binding natural products, which are a sub-group of peptidyl transferase antibiotics. As a peptidyl transferase antibiotic, (+)-Amicetin acts as a universal antibiotic, however it has been shown to be particularly effective against Gram-positive and acid-fast bacteria, especially Mycobacterium, while having also shown antiviral activity.
Due to these properties (+)-Amicetin is of great interest, however to date there is no known total synthesis of (+)-Amicetin, and despite being known for several decades, few other hexopyranosyl cytosines have been synthesised in the lab.
While (+)-Amicetin was not synthesised within the given time, we believe that from a methodological perspective this work has revealed significant knowledge that could prove useful to whomever decides to assume the mantle next.
A number of routes were developed which lead to the amicetamine skeleton both via an α(1→4) glycosidic linkage strategy or starting from a maltoside with the key linkage pre-formed. Both of these routes provide different advantages, with one of the key goals in this project being the ability to synthesise analogues for future development. Both of these routes incorporate this belief, and allow for derivatisation at specific sites within the amicetamine fragment.
Further to this a route to the cytimidine fragment was well developed, with a limitation in the coupling sequence revealed of significant importance to any future chemist aspiring to synthesise (+)-Amicetin.","abstract_html":"(+)-Amicetin is a hexopyranosyl cytosine, a relatively unexplored class of RNA-binding natural products, which are a sub-group of peptidyl transferase antibiotics. As a peptidyl transferase antibiotic, (+)-Amicetin acts as a universal antibiotic, however it has been shown to be particularly effective against Gram-positive and acid-fast bacteria, especially Mycobacterium, while having also shown antiviral activity. <br/><br/>Due to these properties (+)-Amicetin is of great interest, however to date there is no known total synthesis of (+)-Amicetin, and despite being known for several decades, few other hexopyranosyl cytosines have been synthesised in the lab. <br/><br/>While (+)-Amicetin was not synthesised within the given time, we believe that from a methodological perspective this work has revealed significant knowledge that could prove useful to whomever decides to assume the mantle next.<br/><br/>A number of routes were developed which lead to the amicetamine skeleton both via an α(1→4) glycosidic linkage strategy or starting from a maltoside with the key linkage pre-formed. Both of these routes provide different advantages, with one of the key goals in this project being the ability to synthesise analogues for future development. Both of these routes incorporate this belief, and allow for derivatisation at specific sites within the amicetamine fragment.<br/><br/>Further to this a route to the cytimidine fragment was well developed, with a limitation in the coupling sequence revealed of significant importance to any future chemist aspiring to synthesise (+)-Amicetin.","abstract_has_math":false,"creators":["Mackle, Ryan"],"institution":"Queen's University Belfast","degree_name":"Doctor of Philosophy","degree_level":"Doctoral Thesis","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["De Silva, Amilra","Muldoon, Mark"],"committee_chairs":[],"committee_members":[],"year":2022,"date_issued":"2022-7","date_published":"2022-7","updated_at":"2026-07-24T03:56:18Z","subjects":[],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["oai:pure.qub.ac.uk/portal:studenttheses/699b19b0-6576-4d48-9592-93ba3c636bd4"],"render_values":[{"text":"oai:pure.qub.ac.uk/portal:studenttheses/699b19b0-6576-4d48-9592-93ba3c636bd4","href":null,"code":true}]}]},"links":{"outbound_url":"https://pure.qub.ac.uk/en/studentTheses/699b19b0-6576-4d48-9592-93ba3c636bd4","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["De Silva, Amilra","Muldoon, Mark"]},{"key":"dc:contributor.sponsor","label":"Sponsor","values":["Northern Ireland Department for the Economy"]},{"key":"dc:creator","label":"Author","values":["Mackle, Ryan"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2022-7"]},{"key":"dc:date.issued","label":"Date","values":["2022-7"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["School of Chemistry and Chemical Engineering"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["Queen's University Belfast"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://pure.qub.ac.uk/en/studentTheses/699b19b0-6576-4d48-9592-93ba3c636bd4"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["Doctoral Thesis"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["Doctor of Philosophy"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["oai:pure.qub.ac.uk/portal:studenttheses/699b19b0-6576-4d48-9592-93ba3c636bd4","https://pure.qub.ac.uk/en/studentTheses/699b19b0-6576-4d48-9592-93ba3c636bd4"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://pure.qub.ac.uk/files/304348765/Synthetic_Efforts_Towards_the_Total_Synthesis_of_the_Nucleoside_Antibiotic_Amicetin.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["(+)-Amicetin is a hexopyranosyl cytosine, a relatively unexplored class of RNA-binding natural products, which are a sub-group of peptidyl transferase antibiotics. As a peptidyl transferase antibiotic, (+)-Amicetin acts as a universal antibiotic, however it has been shown to be particularly effective against Gram-positive and acid-fast bacteria, especially Mycobacterium, while having also shown antiviral activity.
Due to these properties (+)-Amicetin is of great interest, however to date there is no known total synthesis of (+)-Amicetin, and despite being known for several decades, few other hexopyranosyl cytosines have been synthesised in the lab.
While (+)-Amicetin was not synthesised within the given time, we believe that from a methodological perspective this work has revealed significant knowledge that could prove useful to whomever decides to assume the mantle next.
A number of routes were developed which lead to the amicetamine skeleton both via an α(1→4) glycosidic linkage strategy or starting from a maltoside with the key linkage pre-formed. Both of these routes provide different advantages, with one of the key goals in this project being the ability to synthesise analogues for future development. Both of these routes incorporate this belief, and allow for derivatisation at specific sites within the amicetamine fragment.
Further to this a route to the cytimidine fragment was well developed, with a limitation in the coupling sequence revealed of significant importance to any future chemist aspiring to synthesise (+)-Amicetin."]},{"key":"dc:title","label":"Title","values":["Synthetic efforts towards the total synthesis of the Nucleoside Antibiotic, (+)-Amicetin"]}]}],"canonical_facts":{"dc:contributor.advisor":["De Silva, Amilra","Muldoon, Mark"],"dc:contributor.sponsor":["Northern Ireland Department for the Economy"],"dc:creator":["Mackle, Ryan"],"dc:date":["2022-7"],"dc:date.issued":["2022-7"],"dc:description.abstract":["(+)-Amicetin is a hexopyranosyl cytosine, a relatively unexplored class of RNA-binding natural products, which are a sub-group of peptidyl transferase antibiotics. As a peptidyl transferase antibiotic, (+)-Amicetin acts as a universal antibiotic, however it has been shown to be particularly effective against Gram-positive and acid-fast bacteria, especially Mycobacterium, while having also shown antiviral activity.
Due to these properties (+)-Amicetin is of great interest, however to date there is no known total synthesis of (+)-Amicetin, and despite being known for several decades, few other hexopyranosyl cytosines have been synthesised in the lab.
While (+)-Amicetin was not synthesised within the given time, we believe that from a methodological perspective this work has revealed significant knowledge that could prove useful to whomever decides to assume the mantle next.
A number of routes were developed which lead to the amicetamine skeleton both via an α(1→4) glycosidic linkage strategy or starting from a maltoside with the key linkage pre-formed. Both of these routes provide different advantages, with one of the key goals in this project being the ability to synthesise analogues for future development. Both of these routes incorporate this belief, and allow for derivatisation at specific sites within the amicetamine fragment.
Further to this a route to the cytimidine fragment was well developed, with a limitation in the coupling sequence revealed of significant importance to any future chemist aspiring to synthesise (+)-Amicetin."],"dc:identifier":["oai:pure.qub.ac.uk/portal:studenttheses/699b19b0-6576-4d48-9592-93ba3c636bd4","https://pure.qub.ac.uk/en/studentTheses/699b19b0-6576-4d48-9592-93ba3c636bd4"],"dc:identifier.uri":["https://pure.qub.ac.uk/files/304348765/Synthetic_Efforts_Towards_the_Total_Synthesis_of_the_Nucleoside_Antibiotic_Amicetin.pdf"],"dc:language":["eng"],"dc:publisher.department":["School of Chemistry and Chemical Engineering"],"dc:publisher.institution":["Queen's University Belfast"],"dc:relation.isreferencedby":["https://pure.qub.ac.uk/en/studentTheses/699b19b0-6576-4d48-9592-93ba3c636bd4"],"dc:title":["Synthetic efforts towards the total synthesis of the Nucleoside Antibiotic, (+)-Amicetin"],"dc:type":["Thesis"],"dc:type.qualificationlevel":["Doctoral Thesis"],"dc:type.qualificationname":["Doctor of Philosophy"]},"updated_at":"2026-07-24T03:56:18Z"}