amino acids peptidomimetics peptides protein interactions

Selected Publications

Raffaella Bucci, Sabrina Giofré, Francesca Clerici, Alessandro Contini, Andrea Pinto,
Emanuela Erba, Raffaella Soave, Sara Pellegrino, and Maria Luisa Gelmi; Tetrahydro‑4H‑(pyrrolo[3,4‑d]isoxazol-3-yl)methanamine: A Bicyclic Diamino Scaffold Stabilizing Parallel Turn Conformations; J. Org. Chem. 2018, 83, 19, 11493-11501.

 

Nicolo Tonali, Julia Kaffy, Jean-Louis Soulier, Maria Luisa Gelmi, Emanuela Erba,Myriam Taverna, Carine van Heijenoort, Tap Ha-Duong  Sandrine Ongeri; Structure-activity relationships of beta-hairpin mimics as modulators of amyloid beta-peptide aggregation, European Journal of Medicinal Chemistry, 154 (2018) 280-293.

 

Alessandro Contini, Nicola Ferri, Raffaella Bucci, Maria Giovanna Lupo, Emanuela Erba, Maria Luisa Gelmi, Sara Pellegrino, Peptide modulators of Rac1/Tiam1 protein-protein interaction:
An alternative approach for cardiovascular diseases, Biopolymers. 2017;e23089

Bucci R., Bonetti A., Clerici F., Nava D., Pellegrino S. Tessaro D., Gelmi M.L., Tandem Tetrahydroisoquinoline-4-carboxylic Acid/β-Alanine as a New Construct Able to Induce a Flexible Turn  , Chem. Eur. J., 2017, 23, 10822.

 

Bucci R, Das P., Iannuzzi F., Feligioni M., Gandolfi R., Gelmi M. L., Reches M., Pellegrino S. Self-assembly of an amphipathic ααβ-tripeptide into cationic spherical particles for intracellular delivery, Org. Biomolecular Chem., 2017, 15, 6773.

 

S. Pellegrino, N. Tonali, E. Erba, J. Kaffy, M. Taverna, A. Contini, M. Taylor, D. Allsop, M. L. Gelmia and S. Ongeri, beta-Hairpin mimics containing a piperidine–pyrrolidine scaffold modulate the beta-amyloid aggregation process preserving the monomer species, Chem. Sci., 2017, 8, 1295–1302.

 

F. Selmin, G. Magri, C.G.M. Gennari, S. Marchianò, N. Ferri, S. Pellegrini, Development of poly(lactide-co-glycolide) nanoparticles functionalized with a mitochondria penetrating peptide, J. Pept. Sci. 2017, DOI 10.1002/psc.2952

 

F. Clerici, E. Erba, M.L. Gelmi, S. Pellegrino, Non-standard amino acids and peptides: From self-assembly to nanomaterials,Tetrahedron Letters 57 (2016) 5540–5550.

 

Emanuela Erba, Concetta La Rosa, A novel synthetic approach to the racemic Neuraminidase inhibitor Peramivir, Tetrahedron 72 (2016) 7975-7981.

 

Chiara G. M. Gennari, Silvia Franzè, Sara Pellegrino, Emanuela Corsini, Giulio Vistoli, Luisa Montanari, Paola Minghetti, and Francesco Cilurzo, Skin Penetrating Peptide as a Tool to Enhance the Permeation of Heparin through Human Epidermis, Biomacromolecules, 2016, 17 (1), 46–55.

 

Alessandro Ruffoni,  Maria V. Cavanna, Simona Argentiere, Silvia Locarno, Sara Pellegrino,a Maria Luisa Gelmia and Francesca Clerici, Aqueous self-assembly of short hydrophobic peptides containing norbornene amino acid into supramolecular structures with spherical shape, RSC Adv., 2016,6, 90754-90759.

 

Sara Pellegrino, Giorgio Facchetti, Alessandro Contini, Maria Luisa Gelmi, Emanuela Erba, Raffaella Gandolfi and Isabella Rimoldi, Ctr-1 Mets7 motif inspiring new peptide ligands for Cu(I)-catalyzed asymmetric Henry reactions under green conditions, RSC Adv., 2016,6, 71529-71533.

 

Roberto Benoni, Thelma A. Pertinhez, Francesca Spyrakis, Silvia Davalli, Sara Pellegrino, Gianluca Paredi, Angelica Pezzotti, Stefano Bettati, Barbara Campanini, Andrea Mozzarelli, Structural insight into the interaction of O-acetylserine sulfhydrylase with competitive, peptidic inhibitors by saturation transfer difference-NMR, FEBS Letters,  590 (7), 2016, 943–953.

 

Andrea Bonetti, Sara Pellegrino, Priyadip Das, Sivan Yuran, Raffaella Bucci, Nicola Ferri,Fiorella Meneghetti, Carlo Castellano,Meital Reches, and Maria Luisa Gelmi, Dipeptide Nanotubes Containing Unnatural Fluorine-Substituted β2,3-Diarylamino Acid and L‑Alanine as Candidates for Biomedical Applications,  Org. Lett., 2015, 17 (18), pp 4468–4471

 

Pellegrino S., Bonetti A., Clerici F., Contini A., Moretto A., Soave R., Gelmi M.L.,  1H-Azepin-Oxo-5-amino-5carboxylic acid: a 3-10 helix inducer and an effective tool for functionalized gold nanoparticles, Journal of Organic Chemistry, 2015, 80, 5507-5516.

 

 Ferri, N. ; Facchetti, G. ; Pellegrino, S. ; Ricci, C. ; Curigliano, G. ; Pini, E. ; Rimoldi, I. “Promising antiproliferative platinum(II) complexes based on imidazole moiety: synthesis, evaluation in HCT-116 cancer cell line and interaction with Ctr-1 Met-rich domain”; Bioorganic & Medicinal Chemistry, 2015,  Volume: 23 Issue: 10 Pages: 2538-2547

 

Maffucci, I. ; Pellegrino, S. ; Clayden, J. ; Contini, A. “Mechanism of Stabilization of Helix Secondary Structure by Constrained C alpha-Tetrasubstituted alpha-Amino Acids” Journal of Physical Chemistry B , 2015, Volume: 119 , Issue: 4 , Pages: 1350-1361

 

Ruffoni, A. ; Contini, A. ; Soave, R. ; Lo Presti, L. ; Esposto, I. ; Maffucci, I.; Nava, D. ; Pellegrino, S. ; Gelmi, ML. ; Clerici, F. “Model peptides containing the 3-sulfanylnorbornene amino acid, a conformationally constrained cysteine analogue effective inducer of 3(10)-helix secondary structures” RSC Advances ,2015, Volume: 5, Issue: 41, Pages: 32643-32656

 

Pellegrino, S.; Ronda, L.; Annoni, C. ; Contini, A.; Erba, E.; Gelmi, ML. ; Piano, R.; Paredi, G.; Mozzarelli, A.; Bettati, S. “Molecular insights into dimerization inhibition of c-Maf transcription factor” Biochimica et Biophysica Acta-Proteins and Proteomics ,2014, Volume: 1844 , Issue: 12, Pages: 2108-2115

 

Bonetti, A. ; Clerici, F. ; Foschi, F.; Nava, D.; Pellegrino, S.; Penso, M.; Soave, R.; Gelmi, ML. “syn/anti Switching by Specific Heteroatom-Titanium Coordination in the Mannich-Like Synthesis of 2,3-Diaryl-beta-amino Acid Derivatives”, European Journal of  Organic Chemistry , Volume: 2014 , Issue: 15 , Pages: 3203-3209

 

Pellegrino, S.; Contini, A.; Gelmi, ML.; Lo Presti, L. ; Soave, R ; Erba, E. “Asymmetric Modular Synthesis of a Semirigid Dipeptide Mimetic by Cascade Cycloaddition/Ring Rearrangement and Borohydride Reduction”, Journal of Organic Chemistry , 2014, Volume: 79, Issue: 7, Pages: 3094-3102

 

Ruffoni, A. ; Ferri, N.; Bernini, SK.; Ricci, C. ; Corsini, A.; Maffucci, I.; Clerici, F.; Contini, A., “2-Amino-3-(phenylsulfanyl)norbornane-2-carboxylate: An Appealing Scaffold for the Design of Rac1 Tiam1 Protein-Protein Interaction Inhibitors”, Journal of  Medicinal Chemistry, 2014, Volume: 57, Issue: 7,Pages: 2953-2962

 

Maffucci, I.; Contini, A.,  “Explicit Ligand Hydration Shells Improve the Correlation between MM-PB/GBSA Binding Energies and Experimental Activities”, Journal of Chemical Theory and Computation, Volume: 9, Issue: 6, Pages: 2706-2717

 

Pellegrino, S.; Ruscica, M.; Magni, P. ; Vistoli, G.; Gelmi, ML. “Antiproliferative activity on human prostate carcinoma cell lines of new peptidomimetics containing the spiroazepinoindolinone scaffold”, Bioorganic & Medicinal Chemistry , 2013, Volume: 21, Issue: 17, Pages: 5470-5479

 

Alessandro Ruffoni, Alessandro Casoni, Maria Luisa Gelmi, Sara Pellegrino, Francesca Clerici “Hydroarylation of Substituted Norbornene Amino Acids: Studies on Long-Range Stereo-Electronic Effects on the Regioselectivity of the Addition” Current Organic Chemistry, 2012, 16, 2724-2738.

 

Greco, C. M.; Camera, M.; Facchinetti, L.; Brambilla, M.; Pellegrino, S.; Gelmi, M. L.; Tremoli, E.; Corsini, A.; Ferri, N. “Chemotactic effect of prorenin on human aortic smooth muscle cells: a novel function of the (pro)renin receptor” Cardiovascular research, 2012

 

Pellegrino, S.; Contini, A.; Clerici, F.; Gori, A.; Nava, D.; Gelmi, M. L. “1H-Azepine-4-amino-4-carboxylic acid: a new a,a disubstituted ornithine analogue capable of inducing helix conformations in short Ala-Aib pentapeptides” Chemistry- a European Journal, 2012 doi: 10.1002/chem.201104023

 

Pellegrino, S.; Annoni, C.; Contini, A.; Clerici, F.; Gelmi, M. L. “Expedient chemical synthesis of 75mer DNA binding domain of MafA: an insight on its binding to insulin enhancer” Amino Acids, 2012 doi: 10.1007/s00726-012-1274-2

 

Penso, M.; Foschi, F.; Pellegrino, S.; Testa, A.; Gelmi, M. L. “Diastereoselective protocols for the synthesis of 2,3 trans- and 2,3 cis 6-methoxy-morpholine-2-carboxylic acid derivatives” J. Org. Chem.  2012,  77,  3454-3461.

 

Ruffoni, A., Casoni, A., Pellegrino, S., Gelmi, M.L., Soave, R., Clerici, F. “Sulfanyl-methylene-5(4H)-oxazolones and β-sulfanyl-α-nitroacrylates as appealing dienophiles for the synthesis of conformationally constrained cysteine analogues” Tetrahedron, 2012, 68, 1951-1962.

 

Lanza G., Chiacchio U., Motta S., Pellegrino S., Broggini G. “On the Stability of Polyalanines  Secondary Structures: the Role of Polyproline II Helix” Chem. Phys. Chem. 2011, 12, 2724-2727

 

Gassa, F.; Contini, A.; Fontana, G.; Pellegrino, S.; Gelmi, M.L. “A Highly Diastereoselective “Synthesis of a-Hydroxy-b-amino Acid Derivatives via a Lewis Acid Catalyzed Three-Component Condensation Reaction.”    J. Org. Chem.  2010,  75,  7099-7106.

 

Pellegrino, S.; Ferri, N.; Colombo, N.;  Cremona, E.;Corsini, A.; Fanelli, R.; Gelmi, M. L.; Cabrele C. “Synthetic peptides containing a conserved sequence motif of the Id protein family modulate vascular smooth muscle cell phenotype” Bioorg. Med. Chem. Lett., 2009, 19, 6298–6302.

 

  1. Pellegrino, F. Clerici, M. L. Gelmi “b-Hydroxynorbornane amino acid derivatives: valuable synthons for the diastereoselective synthesis preparation of substituted cyclopentylglycines derivatives” Tetrahedron 2008, 64, 5657-566

 

  1. L. Gelmi, F. Clerici, R. Gandolfi, S. Pellegrino “A new efficient synthesis of enantiopure diasteromeric 3’-aminocyclopentylglycines” Tetrahedron-Asymmetry 2008, 19, 584-592

 

  1. L. Gelmi, C. Cattaneo, S. Pellegrino, F. Clerici, M. Montali, C. Martini “An efficient route to all stereoisomeric enantiopure 6-amino-3-alkyl-3-azabicyclo[3.2.1]octane-6-carboxylic acids” J. Org. Chem. 2007, 72, 9811-9814.

 

  1. L. Gelmi, F. Caputo, F. Clerici, S. Pellegrino, G. Giannaccini, L. Betti, L. Fabbrini, L. Schmid, L. Palego, A. Lucacchini “1-Aminocyclopentane-1,2,4-tricarboxylic acids screening on glutamatergic and serotonergic systems” Bioorg. Med. Chem., 2007, 15, 7581–7589

 

F.Caputo, C. Cattaneo, F. Clerici, M.L. Gelmi, S. Pellegrino “a,g-Diamino Acids: Asymmetric Synthesis of New Constrained 6-Amino-3 azabicyclo[3.2.1] octane-6-carboxylic Acids” J. Org. Chem. 2006, 71, 8467-8472.

 

  1. Caputo, F. Clerici, M.L Gelmi, S. Pellegrino, D. Pocar “An efficient synthesis of new diastereomeric enantiopure 1-aminocyclopentane-1,2,4-tricarboxylic acids” Tetrahedron:Asymmetry, 2006, 17, 1430-1436.

 

  1. Cabrele, F. Clerici, M.L. Gelmi, R. Gandolfi, F. Molinari, S. Pellegrino “Chemoenzymatic resolution of epimeric cis 3-carboxycylopentylglycine derivatives” Tetrahedron, 2006, 62, 3502-3508

 

  1. Caputo, F. Clerici, M.L Gelmi, S. Pellegrino, T. Pilati “Enantioselective Synthesis of Epimeric cis  3-Carboxycylopentylglycines” Tetrahedron:Asymmetry, 2006, 17, 61-67.

 

  1. Caputo, F. Clerici, M. L. Gelmi, D. Nava, S. Pellegrino “Uncatalyzed Solventless Diels-Alder Reaction of 2-Amino-3-nitroacrylate: Synthesis of New Epimeric 2-Amino-3-nitro-norbornene- and norbornane-2-carboxylic Acids” Tetrahedron, 2006, 62,1288-1294

 

  1. Clerici, M. L. Gelmi, S. Pellegrino, T. Pilati “3-Formylcyclopent-3-enyl- and 3-carboxycyclopentylglycine Derivatives: a New Stereocontrolled Approach via Retro-aldol or Retro-Claisen Reactions” J. Org. Chem. 2003, 68, 5286.

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