Martina De Angelis

Dottoressa di ricerca

ciclo: XXXIII



Titolo della tesi: Stereocontrolled Total Synthesis of Iminosugars and Their Derivatives with Potential Therapeutic Activities

Iminosugars are polyhydroxylated compounds which differ from the carbohydrates in the presence of the endocyclic nitrogen atom in place of the oxygen. Iminosugars are able to interact with numerous fundamental enzymes by mimicking the sugars, hence, they have tremendous potential applicability as therapeutics in a vast array of disease, such as cancer, diabetes, lysosomal storage disorders and viral infections. The significant biomedical implications of iminosugars has aroused the interest in the research of new strategies aimed at obtaining them. In this work, I report our stereocontrolled total synthetic approach which provides the access to several classes of diastereomeric iminosugars from a common precursor, while controlling the four contiguous stereocenters. The control of the four contiguous stereocenters is achieved through an opportune sequence of stereocontrolled key steps: the asymmetric Sharpless epoxidation, the asymmetric dihydroxylation (or amino hydroxylation), and the epoxide ring opening with suitable nucleophiles. Through the opportune sequence of the key steps listed above, the choice of the chiral ligands and the suitable nucleophiles in the epoxide ring opening, after the optimization of some crucial steps, is possible to obtain a large library of iminosugars and their derivatives, starting from a common precursor. Once obtained, the iminosugars will be tested for their biological activity. Furthermore, the possibility to anchor iminosugars to magnetic nanoparticles will enable further studies regarding their applicability in the drug delivery field.

Produzione scientifica

11573/1700797 - 2024 - Stereoselectivity in electrosprayed confined volumes: asymmetric synthesis of warfarin by diamine organocatalysts in microdroplets and thin films
De Angelis, Martina; Managò, Marta; Pepi, Federico; Salvitti, Chiara; Troiani, Anna; Villani, Claudio; Ciogli, Alessia - 01a Articolo in rivista
rivista: RSC ADVANCES (London: Royal Society of Chemistry) pp. 1576-1580 - issn: 2046-2069 - wos: WOS:001135870900001 (0) - scopus: 2-s2.0-85181778604 (0)

11573/1702295 - 2024 - A C3‐Symmetric Amino Organocatalyst for Asymmetric Synthesis of Warfarin and Analogues: Mechanistic Insight from ESI‐MS Spectrometry and Computational Calculations
Sorato, Andrea; De Angelis, Martina; Oljira, Shilashi Badasa; Pierini, Marco; Mazzoccanti, Giulia; Donzello, Maria Pia; Ciogli, Alessia - 01a Articolo in rivista
rivista: CHEMCATCHEM (Weinheim : Wiley-VCH) pp. - - issn: 1867-3880 - wos: (0) - scopus: (0)

11573/1693710 - 2023 - Stereocontrolled synthesis of new iminosugar lipophilic derivatives and evaluation of biological activities
De Angelis, Martina; Primitivo, Ludovica; Sappino, Carla; Centrella, Barbara; Lucarini, Claudia; Lanciotti, Lucrezia; Petti, Alessia; Odore, Davide; D'annibale, Andrea; Macchi, Beatrice; Stefanizzi, Valeria; Cirigliano, Angela; Rinaldi, Teresa; Righi, Giuliana; Ricelli, Alessandra - 01a Articolo in rivista
rivista: CARBOHYDRATE RESEARCH (Elsevier Science Limited:Oxford Fulfillment Center, PO Box 800, Kidlington Oxford OX5 1DX United Kingdom:011 44 1865 843000, 011 44 1865 843699, EMAIL: asianfo@elsevier.com, tcb@elsevier.co.UK, INTERNET: http://www.elsevier.com, http://www.elsevier.com/locate/shpsa/, Fax: 011 44 1865 843010) pp. - - issn: 0008-6215 - wos: WOS:001119492200001 (0) - scopus: 2-s2.0-85177497569 (0)

11573/1699500 - 2023 - Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
Goggiamani, Antonella; Arcadi, Antonio; Ciogli, Alessia; De Angelis, Martina; Dessalvi, Stefano; Fabrizi, Giancarlo; Iavarone, Federica; Iazzetti, Antonia; Sferrazza, Alessio; Zoppoli, Roberta - 01a Articolo in rivista
rivista: RSC ADVANCES (London: Royal Society of Chemistry) pp. 10090-10096 - issn: 2046-2069 - wos: WOS:000962421400001 (0) - scopus: 2-s2.0-85168759017 (0)

11573/1664751 - 2022 - Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy
Arcadi, A.; Berden, G.; Ciogli, A.; Corinti, D.; Crestoni, M. E.; De Angelis, M.; Fabrizi, G.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Marsicano, V.; Oomens, J.; Serraiocco, A. - 01a Articolo in rivista
rivista: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (Weinheim : Wiley-VCH-Verl.) pp. - - issn: 1099-0690 - wos: WOS:000884495100001 (1) - scopus: 2-s2.0-85142364350 (2)

11573/1643176 - 2022 - Preparation of a high-density vinyl silica gel to anchor cysteine via photo-click reaction and its applications in hydrophilic interaction chromatography
Ciogli, Alessia; Buonsenso, Fabio; Proietti, Noemi; Mazzoccanti, Giulia; Manetto, Simone; Calcaterra, Andrea; De Angelis, Martina; Gasparrini, Francesco - 01a Articolo in rivista
rivista: JOURNAL OF CHROMATOGRAPHY A (Elsevier BV:PO Box 211, 1000 AE Amsterdam Netherlands:011 31 20 4853757, 011 31 20 4853642, 011 31 20 4853641, EMAIL: nlinfo-f@elsevier.nl, INTERNET: http://www.elsevier.nl, Fax: 011 31 20 4853598) pp. - - issn: 0021-9673 - wos: WOS:000809820900010 (6) - scopus: 2-s2.0-85131091984 (7)

11573/1608565 - 2022 - Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar
De Angelis, M.; Primitivo, L.; Lizzio, F.; Agostinelli, S.; Sappino, C.; Ben Romdan, I.; Bonanni, L.; D'annibale, A.; Antonioletti, R.; Ricelli, A.; Righi, G. - 01a Articolo in rivista
rivista: CARBOHYDRATE RESEARCH (Elsevier Science Limited:Oxford Fulfillment Center, PO Box 800, Kidlington Oxford OX5 1DX United Kingdom:011 44 1865 843000, 011 44 1865 843699, EMAIL: asianfo@elsevier.com, tcb@elsevier.co.UK, INTERNET: http://www.elsevier.com, http://www.elsevier.com/locate/shpsa/, Fax: 011 44 1865 843010) pp. 108484- - issn: 0008-6215 - wos: WOS:000829967600001 (1) - scopus: 2-s2.0-85121206374 (1)

11573/1664752 - 2022 - Asymmetric Hydroarylation Reactions Catalyzed by Transition Metals: Last 10 Years in a Mini Review
De Angelis, Martina; Iazzetti, Antonia; Serraiocco, Andrea; Ciogli, Alessia - 01a Articolo in rivista
rivista: CATALYSTS (Basel: Molecular Diversity Preservation International) pp. 1289- - issn: 2073-4344 - wos: WOS:000872708500001 (3) - scopus: 2-s2.0-85140835097 (3)

11573/1544065 - 2021 - Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin
De Angelis, M.; Sappino, C.; Mandic, E.; D'alessio, M.; De Dominicis, M. G.; Sannino, S.; Primitivo, L.; Mencarelli, P.; Ricelli, A.; Righi, G. - 01a Articolo in rivista
rivista: TETRAHEDRON (Elsevier Science Limited:Oxford Fulfillment Center, PO Box 800, Kidlington Oxford OX5 1DX United Kingdom:011 44 1865 843000, 011 44 1865 843699, EMAIL: asianfo@elsevier.com, tcb@elsevier.co.UK, INTERNET: http://www.elsevier.com, http://www.elsevier.com/locate/shpsa/, Fax: 011 44 1865 843010) pp. 131837- - issn: 0040-4020 - wos: WOS:000604923900013 (4) - scopus: 2-s2.0-85097797551 (5)

11573/1608286 - 2021 - Preparation and Asymmetric Induction Evaluation of the First Ephedrine-Based Ligands Immobilized on Magnetic Nanoparticles
Primitivo, L.; Sappino, C.; De Angelis, M.; Righi, F.; Iannoni, M.; Lucci, G.; Luzzitelli, G.; Suber, L.; Leonelli, F.; Ricelli, A.; Righi, G. - 01a Articolo in rivista
rivista: ACS OMEGA (Washington, D.C. : American Chemical Society, 2016-) pp. 35641-35648 - issn: 2470-1343 - wos: WOS:000733830700001 (2) - scopus: 2-s2.0-85122002549 (3)

11573/1560253 - 2021 - Fine-tuning synthesis of fluorescent silver thiolate nanoclusters
Suber, Lorenza; Pilloni, Luciano; Khanna, Kshitij; Righi, Giuliana; Primitivo, Ludovica; De Angelis, Martina; Caschera, Daniela - 01a Articolo in rivista
rivista: JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY (Stevenson Ranch Calif.: American Scientific Publishers, 2001-) pp. 2816-2823 - issn: 1533-4880 - wos: (0) - scopus: (0)

11573/1415939 - 2020 - Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol
De Angelis, M.; Primitivo, L.; Lucarini, C.; Agostinelli, S.; Sappino, C.; Ricelli, A.; Righi, G. - 01a Articolo in rivista
rivista: CARBOHYDRATE RESEARCH (Elsevier Science Limited:Oxford Fulfillment Center, PO Box 800, Kidlington Oxford OX5 1DX United Kingdom:011 44 1865 843000, 011 44 1865 843699, EMAIL: asianfo@elsevier.com, tcb@elsevier.co.UK, INTERNET: http://www.elsevier.com, http://www.elsevier.com/locate/shpsa/, Fax: 011 44 1865 843010) pp. 1-6 - issn: 0008-6215 - wos: WOS:000537685600006 (8) - scopus: 2-s2.0-85084386786 (8)

11573/1466407 - 2020 - Antioxidant and biological activities of hydroxytyrosol and homovanillic alcohol obtained from olive mill wastewaters of extra-virgin olive oil production
Ricelli, Alessandra; Gionfra, Fabio; Percario, Zulema; De Angelis, Martina; Primitivo, Ludovica; Bonfantini, Veronica; Antonioletti, Roberto; Bullitta, Simonetta Maria; Saso, Luciano; Incerpi, Sandra; Pedersen, Jens Zacho - 01a Articolo in rivista
rivista: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (American Chemical Society:1155 Sixteenth Street Northwest:Washington, DC 20036:(800)227-5558, EMAIL: service@acs.org, INTERNET: http://www.pubs.acs.org, Fax: (614)447-3671) pp. 1-11 - issn: 0021-8561 - wos: WOS:000605190400008 (7) - scopus: 2-s2.0-85098795727 (10)

11573/1469688 - 2020 - Linear β-amino alcohol catalyst anchored on functionalized magnetite nanoparticles for enantioselective addition of dialkylzinc to aromatic aldehydes
Sappino, C.; Primitivo, L.; De Angelis, M.; Righi, Francesco; Di Pietro, F.; Iannoni, M.; Pilloni, L.; Vecchio Ciprioti, S.; Suber, L.; Ricelli, A.; Righi, G. - 01a Articolo in rivista
rivista: RSC ADVANCES (London: Royal Society of Chemistry) pp. 29688-29695 - issn: 2046-2069 - wos: WOS:000561946700009 (5) - scopus: 2-s2.0-85093087690 (6)

11573/1346610 - 2019 - Stereodivergent sinthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin by using the asymmetric dihydroxylation reaction as key step
De Angelis, Martina; Agostinelli, Sonia; Centrella, Barbara; Forte, Giorgia; Lanciotti, Lucrezia; Lucarini, Claudia; . Luciani, Alessandro; Odore, Davide; Righi, Giuliana - 04d Abstract in atti di convegno
congresso: XLIV "A. Corbella" International Summer School on Organic Synthesis - ISOS 2019, Gargnano 9-13 Giugno 2019 (Gargnano)
libro: XLIV "A. Corbella" International Summer School on Organic Synthesis - ISOS 2019 - ()

11573/1346629 - 2019 - Stereocontrolled synthesis of pyrrolidine iminosugars through asymmetric dihydroxylation reaction
De Angelis, Martina; Agostinelli, Sonia; Forte, Giorgia; Lucarini, Claudia; Sappino, Carla; Giuliana, Righi - 04d Abstract in atti di convegno
congresso: Merck Young Chemists’ Symposium 2019 (Rimini)
libro: Merck Young Chemists’ Symposium XIX edition - ()

11573/1346616 - 2019 - Stereocontrolled synthesis of pyrrolidine iminosugars’ lipophilic derivatives
De Angelis, Martina; Lanciotti, Lucrezia; Lucarini, Claudia; Forte, Giorgia; Odore, Davide; Ricelli, Alessandra; Righi, Giuliana - 04d Abstract in atti di convegno
congresso: XXXIX Convegno Nazionale della Divisione di Chimica Organica della Società Chimica Italiana, CDCO, Torino 8-12 Settembre 2019 (Torino)
libro: XXXIX Convegno Nazionale della Divisione di Chimica Organica della Società Chimica Italiana, CDCO, Torino 8-12 Settembre 2019 - ()

11573/1346633 - 2019 - Role of some food-grade synthesized flavonoids on the control of ochratoxin a in aspergillus carbonarius
Ricelli, A.; De Angelis, M.; Primitivo, L.; Righi, G.; Sappino, C.; Antonioletti, R. - 01a Articolo in rivista
rivista: MOLECULES (Basel: MDPI Berlin: Springer, 1996-) pp. 1-10 - issn: 1420-3049 - wos: WOS:000482303000036 (9) - scopus: 2-s2.0-85068925934 (10)

11573/1346674 - 2019 - Functionalized magnetic nanoparticles as catalysts for enantioselective Henry reaction
Sappino, Carla; Primitivo, Ludovica; De Angelis, Martina; Oneto Domenici, Marzia; Mastrodonato, Andrea; Ben Romdan, Ilaria; Tatangelo, Chiara; Suber, Lorenza; Pilloni, Luciano; Ricelli, Alessandra; Righi, Giuliana - 01a Articolo in rivista
rivista: ACS OMEGA (Washington, D.C. : American Chemical Society, 2016-) pp. 21809-21817 - issn: 2470-1343 - wos: WOS:000504635000018 (13) - scopus: 2-s2.0-85076630410 (16)

11573/1187855 - 2018 - Stereocontrolled synthesis of pyrrolidine iminosugars through asymmetric dihydroxylation of optically active olefins
De Angelis, Martina; Agostinelli, Sonia; Forte, Giorgia; Lucarini, Claudia; Righi, Giuliana; Sappino, Carla - 04f Poster
congresso: Spanish-Italian Symposium on Organic Chemistry, (SISOC-XII) (Ferrara)
libro: Book of Abstract - ()

11573/1188056 - 2018 - Regio- and stereocontrol in asymmetric aminohydroxylation reaction on unsaturated azido alcohols
De Angelis, Martina; Ben Romdan, Ilaria; Giorgia, Forte; Petti, Alessia; Giuliana, Righi - 04f Poster
congresso: XXXVIII Convegno Nazionale della Divisione di Chimica Organica della Società Chimica Italiana (Milano)
libro: Book of Abstract - ()

11573/1188028 - 2018 - Study of asymmetric aminohydroxylation reaction aimed at the synthesis of aminoiminosugars
De Angelis, Martina; Lanciotti, Lucrezia; Lizzio, Federica; Righi, Giuliana; Sappino, Carla - 04f Poster
congresso: XXII International Conference on Organic Synthesis – 22-ICOS (Firenze)
libro: Book of Abstract - ()

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