Publicação
Synthetic Approaches and Computational Studies of Naturally Occurring Phenolic Carbohydrate Esters as Lead Pharmaceutics
| Resumo: | Carbohydrates are vital for living systems and can contribute to the treatment of various diseases. However, more research is needed on sucrose-derived compounds due to their availability and low cost. Phenolic Sucrose Esters (PSEs), known for their antioxidant and anti-inflammatory properties, among others, are rarely synthesised, which, combined with the small amounts isolated from plants, limits their use in pharmacology. With this project, we explored one-step selective chemical methodologies, under Mitsunobu conditions, to synthesise a total of 14 biologically active sucrose esters: six mono- esters, which were our target compounds, resulting in a range of relatively good yields (17 – 33%), and additionally two per-acetylated mono-esters and six di-esters, all with promising applications. It is important to note that this is the first record of successfully synthesising 6,6’-di-O-feruloyl sucrose ester, 6,6’-di-O-sinapoyl sucrose ester, 6-O-syringyl sucrose ester, 6,6’-di-O-syringyl sucrose ester, 6-O-vanillyl sucrose ester, 6,6’-di-O-vanillyl sucrose ester and 1’,2,3,3’,4,4’,6’-hepta-O-acetil-6-O-benzoyl sucrose ester. A part of the project included a computational estimation of the radical scavenging effects of some of these compounds through different reaction pathways - hydrogen atom transfer (HAT), single electron transfer (SET) and radical adduct formation (RAF). Except for 6-O-benzoyl sucrose ester, all the mono-esters were able to deactivate the three free radicals used in the study (•ОСН3, •ООН, and •ООСН3) either in the HAT or in both HAT and RAF mechanisms. |
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| Autores principais: | Maciel, Verónica Raissa dos Santos |
| Assunto: | sucrose phenolic sucrose esters esterification Mitsunobu reaction computational studies radical scavenging |
| Ano: | 2024 |
| País: | Portugal |
| Tipo de documento: | dissertação de mestrado |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade Nova de Lisboa |
| Idioma: | inglês |
| Origem: | Repositório Institucional da UNL |
| Resumo: | Carbohydrates are vital for living systems and can contribute to the treatment of various diseases. However, more research is needed on sucrose-derived compounds due to their availability and low cost. Phenolic Sucrose Esters (PSEs), known for their antioxidant and anti-inflammatory properties, among others, are rarely synthesised, which, combined with the small amounts isolated from plants, limits their use in pharmacology. With this project, we explored one-step selective chemical methodologies, under Mitsunobu conditions, to synthesise a total of 14 biologically active sucrose esters: six mono- esters, which were our target compounds, resulting in a range of relatively good yields (17 – 33%), and additionally two per-acetylated mono-esters and six di-esters, all with promising applications. It is important to note that this is the first record of successfully synthesising 6,6’-di-O-feruloyl sucrose ester, 6,6’-di-O-sinapoyl sucrose ester, 6-O-syringyl sucrose ester, 6,6’-di-O-syringyl sucrose ester, 6-O-vanillyl sucrose ester, 6,6’-di-O-vanillyl sucrose ester and 1’,2,3,3’,4,4’,6’-hepta-O-acetil-6-O-benzoyl sucrose ester. A part of the project included a computational estimation of the radical scavenging effects of some of these compounds through different reaction pathways - hydrogen atom transfer (HAT), single electron transfer (SET) and radical adduct formation (RAF). Except for 6-O-benzoyl sucrose ester, all the mono-esters were able to deactivate the three free radicals used in the study (•ОСН3, •ООН, and •ООСН3) either in the HAT or in both HAT and RAF mechanisms. |
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