CHEMICALS FROM BIOMASS The challenges of a sustainable development includes the availability of renewable raw materials employing natural sources,associated to the reduction of energetic consumption and limiting the environmental impact. In the chemical language this concept is well expressed by the term “Green Chemistry”.1 Vegetable plants and wood deriving biomass is mainly based on cellulose composition, in addition to lignin, terpenesand resins. They are employed as a source of fuels by termochemical conversion, by a process furnishing a viscous bio-oil containing several chemical species which are a potential gold-mine of peculiar organic compounds. On the opposite side to oil-refineries related to petroleum chemistry, biorefineries involve chemicals deriving from renewable natural sources. Their main activities arerelated to the production of biofuels,but also of compounds having a high value-added in terms of molecular complexity, usable as fine chemicals difficult to be obtained in other ways. The advantages related to biorefineries represent a topic currently of interest in academia, industry,economy and politics. PRODUCTION OF LAC BY CELLULOSE PYROLYSIS Quantitative pyrolysis of cellulose catalyzed by titanium alluminate nanoparticlesafforded a mixture of known anhydrosugars with a previously left in the shadowshydroxylactone(LAC), now obtained in improved amount in comparison with other catalyticsystems and fully characterized.2 Optimized chromatographic purification allowed to obtain LAC in gram-scale with12% yield from cellulose. Experiments have been planned in order to obtain LAC from pyrolysis of lingo-cellulosic materials. This research activity is carried out in Ravenna atCentro Interdipartimentale di Ricerca Industriale Energia e Ambiente, Universityof Bologna, which provides the compound LAC forits further application in organic synthesis. LAC AS CHIRAL BUILDING BLOCK IN THE SYNTHESIS OF BIOACTIVE MOLECULES LAC has been recognized as an interesting chiral building block to be used in the synthesis of biologically active molecules.3 Its chiral features make it a suitable candidate for the access to single stereoisomers, respecting the essential requirement for the interactions with biological receptors, as known for the specific therapeutic action of many drugs. Recently LAC has been used for the production of a new furanoidaminoacid,3useful for peptidomimetic applications and currently employed for obtaining analogues of the natural muscarine to be studied for their biological activities.In fact compounds having muscarine-like activity are of great interest in order to achieve new selective agents in the therapeutic treatment of Alzheimer’s disease.Another application of LAC is related to the synthesis of new molecules as potential antiviral agents, with a nucleoside structure able to inhibit HIV and hepatitis C. Thesenew derived compounds preserve the chiral unit present in LAC, which is linked to purine or triazole moieties. These synthetic strategies involve eco-friendly methods, as reactions assisted by microwave irradiation which replacesthe conventional heating and avoidslong reaction times as well as the presence of solvents.2 This research activity is carried out at the University of Trento, currently granted by ENAM project (ProvinciaAutonoma di Trento-CNR di Napoli). REFERENCES 1 -Noyori R. Chemical Communications, 2005, 14, 1807 – 1811. 2 - FabbriD., TorriC., ManciniI.Green Chemistry, 2007, 9, 1374-1379. 3- Defant A., Mancini I., Torri C.,Malferrari D., Fabbri D. AminoAcids, 2011, 40, 633-640.

FROM BIOMASS TO MEDICINES: THE APPLICATION OF A PRODUCT FROM CELLULOSE PYROLYSIS IN THE PRODUCTION OF BIOACTIVE MOLECULES

Dosi, Federico;Defant, Andrea;Mancini, Ines
2013

Abstract

CHEMICALS FROM BIOMASS The challenges of a sustainable development includes the availability of renewable raw materials employing natural sources,associated to the reduction of energetic consumption and limiting the environmental impact. In the chemical language this concept is well expressed by the term “Green Chemistry”.1 Vegetable plants and wood deriving biomass is mainly based on cellulose composition, in addition to lignin, terpenesand resins. They are employed as a source of fuels by termochemical conversion, by a process furnishing a viscous bio-oil containing several chemical species which are a potential gold-mine of peculiar organic compounds. On the opposite side to oil-refineries related to petroleum chemistry, biorefineries involve chemicals deriving from renewable natural sources. Their main activities arerelated to the production of biofuels,but also of compounds having a high value-added in terms of molecular complexity, usable as fine chemicals difficult to be obtained in other ways. The advantages related to biorefineries represent a topic currently of interest in academia, industry,economy and politics. PRODUCTION OF LAC BY CELLULOSE PYROLYSIS Quantitative pyrolysis of cellulose catalyzed by titanium alluminate nanoparticlesafforded a mixture of known anhydrosugars with a previously left in the shadowshydroxylactone(LAC), now obtained in improved amount in comparison with other catalyticsystems and fully characterized.2 Optimized chromatographic purification allowed to obtain LAC in gram-scale with12% yield from cellulose. Experiments have been planned in order to obtain LAC from pyrolysis of lingo-cellulosic materials. This research activity is carried out in Ravenna atCentro Interdipartimentale di Ricerca Industriale Energia e Ambiente, Universityof Bologna, which provides the compound LAC forits further application in organic synthesis. LAC AS CHIRAL BUILDING BLOCK IN THE SYNTHESIS OF BIOACTIVE MOLECULES LAC has been recognized as an interesting chiral building block to be used in the synthesis of biologically active molecules.3 Its chiral features make it a suitable candidate for the access to single stereoisomers, respecting the essential requirement for the interactions with biological receptors, as known for the specific therapeutic action of many drugs. Recently LAC has been used for the production of a new furanoidaminoacid,3useful for peptidomimetic applications and currently employed for obtaining analogues of the natural muscarine to be studied for their biological activities.In fact compounds having muscarine-like activity are of great interest in order to achieve new selective agents in the therapeutic treatment of Alzheimer’s disease.Another application of LAC is related to the synthesis of new molecules as potential antiviral agents, with a nucleoside structure able to inhibit HIV and hepatitis C. Thesenew derived compounds preserve the chiral unit present in LAC, which is linked to purine or triazole moieties. These synthetic strategies involve eco-friendly methods, as reactions assisted by microwave irradiation which replacesthe conventional heating and avoidslong reaction times as well as the presence of solvents.2 This research activity is carried out at the University of Trento, currently granted by ENAM project (ProvinciaAutonoma di Trento-CNR di Napoli). REFERENCES 1 -Noyori R. Chemical Communications, 2005, 14, 1807 – 1811. 2 - FabbriD., TorriC., ManciniI.Green Chemistry, 2007, 9, 1374-1379. 3- Defant A., Mancini I., Torri C.,Malferrari D., Fabbri D. AminoAcids, 2011, 40, 633-640.
CONFERENZA INTERNAZIONALE SULLA RICERCA SULLA CHIMICA VERDE E BIOBASED ECONOMY “Green Chemistry, a first step towards Bioeconomy
D., Fabbri; D., Malferrari; Dosi, Federico; Defant, Andrea; Mancini, Ines
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11572/68098
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