Dr Vittorio Caprio

Academic and professional qualifications

Vittorio Caprio graduated with a degree in Chemistry from The University of Reading in 1994 and a PhD, in Organic Synthesis, from the same institution, in 1998. He subsequently moved to The University of Auckland, New Zealand to carry out postdoctoral work followed by a lectureship in 2001.

In 2009 he relocated back to the UK to take up his current post at Manchester Metropolitan University.

Other academic service (administration and management)

Research expertise

The main research interests of the Caprio group are focused on the development of novel synthetic routes to bioactive natural products and their use in interdisciplinary studies in chemical biology/drug lead generation. We have special interests in:

1. The use of nitrones in organic synthesis. We have developed routes tochiral, non-racemic nitrone derivatives of 3-hydroxypiperidines and functionalised tetrahydroisoquinolines which provide access to a range of sterodefined products

2. Construction of spirocyclic alkaloid scaffolds. The group utilize an intramolecular cycloaddition/oxidative ring opening strategy to access core structure analogues of a range of spirocyclic alkaloids including pinnaic acid, halichlorine and histrionicotoxin.

3. Biocatalysis in the total synthesis of complex alkaloids. We have pioneered the coupling of a transaminase mediated-reductive amination/aza-Michael cascade for the highly efficient enantioselective preparation of alkaloid scaffolds.

4. Development of drug leads which to disrupt a number of antiinflammatory mechanisms included inhibition of CRP dissociation, Il-1 antagonism and inhibition of PLA2 activity.

Academic collaborations

1. Transaminase-mediated RA/IMAMR cascades for the preparation of alkaloid scaffolds. With Elaine O'Reilly (Uni. of Nottingham), Beatriz Macia Ruiz (MMU).

2. Development of azaspirocycles as novel antiinflammatories, antimicrobials and treatments for chronic wound healing. With Jason Ashworth, Kathryn Whitehead

3. Development of small molecules to prevent  pCRP to mCRP dissociation and inhibitors of IL-1 receptor. With Prof Mark Slevin.

Publications

• Books (authored/edited/special issues)

  V. Caprio, J. Williams, . Caprio, Williams (2009). Catalysis in Asymmetric Synthesis. John Wiley & Sons.

• Journal articles

  H. Eastman, J. Ryan, V. Caprio, B. Maciá, E. O'Reilly (2019). Alcohol Dehydrogenase Triggered Oxa‐Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans. ChemCatChem. 11(16), pp.3760-3762.

  J. Flores-Ferrándiz, N. Carter, MJ. González-Soria, M. Wasinska, D. Gill, et al. B. Maciá, V. Caprio. (2018). Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides. Organic and Biomolecular Chemistry. 16(38), pp.6961-6968.

  J. Ryan, M. Šiaučiulis, A. Gomm, B. Maciá, E. O’Reilly, et al. V. Caprio. (2016). Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds. Journal of the American Chemical Society. 138(49), pp.15798-15800.

  G. Archibald, CP. Lin, P. Boyd, D. Barker, V. Caprio (2012). A divergent approach to 3-piperidinols: A concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton. Journal of Organic Chemistry. 77(18), pp.7968-7980.

  LA. Stubbing, FF. Li, DP. Furkert, VE. Caprio, MA. Brimble (2012). Access to 2-alkyl chromanones via a conjugate addition approach. Tetrahedron. 68(34), pp.6948-6956.

  V. Caprio, J. Ward, A. Johnson, G. Clark (2009). The Synthesis of Functionalised Bicyclo[3.3.1]nonanes Related to Huperzine A. Synthesis. 2009(20), pp.3411-3418.

  A. Ashoorzadeh, G. Archibald, V. Caprio (2009). Synthetic evaluation of an enantiopure tetrahydropyridine N-oxide. Synthesis of (+)-febrifugine. Tetrahedron. 65(24), pp.4671-4680.

  V. Caprio, J. Ward (2009). Synthesis of the Bicyclo[3.3.1]nonane Core of Huperzine A and Novel Pyridine-Fused Tricycles by Cyclisation of Pyridine-Based Radicals. HETEROCYCLES. 79(1), pp.791-791.

  S-H. Yang, GR. Clark, V. Caprio (2009). A concise approach to the core structures of pinnaic acid and halichlorine. Organic & Biomolecular Chemistry. 7(14), pp.2981-2981.

  M. Brimble, D. Crimmins, I. Dimitrov, P. O’Connor, V. Caprio (2008). A Facile Synthesis of a Spironitrone and a Study of Its Cycloaddition and Nucleophilic Addition Reactions. Synthesis. 2008(20), pp.3319-3325.

  V. Caprio, S-H. Yang (2007). A Concise and Flexible Synthesis of the Core Structure of Pinnaic Acid. Synlett. 2007(08), pp.1219-1222.

  H. Peng, C. Soeller, NA. Vigar, V. Caprio, J. Travas-Sejdic (2007). Label-free detection of DNA hybridization based on a novel functionalized conducting polymer. Biosens Bioelectron. 22(9-10), pp.1868-1873.

  V. Caprio (2006). Recent Advances in Organocopper Chemistry. Letters in Organic Chemistry. 3(5), pp.339-349.

  J. Ward, V. Caprio (2006). A radical mediated approach to the core structure of huperzine A. Tetrahedron Letters. 47(4), pp.553-556.

  V. Caprio, A. Ashoorzadeh (2005). A Convergent Enantioselective Synthesis of the Anti-Malarial Agent (+)-Febrifugine. Synlett. pp.346-348.

  V. Caprio, MA. Brimble, DP. Furkert (2001). Synthesis of the novel 1,7,9-trioxadispiro[4.1.5.2]-tetradecane ring system present in the spirolides. Tetrahedron. 57(18), pp.4023-4034.

  MA. Brimble, V. Caprio, AD. Johnston, M. Sidford (2001). Synthesis of Arylspiroketals Related to the Papulacandins via Generation of Phthalide Oxycarbenium Ions. Synthesis. 2001(06), pp.0855-0862.

  MA. Brimble, V. Caprio, AD. Johnston, M. Sidford (2001). Synthesis of arylspiroketals related to the papulacandins via generation of phthalide oxycarbenium ions. Synthesis. pp.855-862.

  VE. Caprio, MW. Jones, MA. Brimble (2001). 1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl) propanal O-methyloxime. Molecules. 6(3),

  VE. Caprio, MW. Jones, MA. Brimble (2001). 1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol. Molecules. 6(3),

  VE. Caprio, MW. Jones, MA. Brimble (2001). 1-(Pyridin-3-yl)but-2-yn-1,4-diol. Molecules. 6(3),

  VE. Caprio, MW. Jones, MA. Brimble (2001). Pyridine-3-carboxaldehyde O-methyloxime. Molecules. 6(3),

  VE. Caprio, MW. Jones, MA. Brimble (2001). tert-Butyl methoxy(2-propynyl)carbamate. Molecules. 6(3),

  V. Caprio, B. Guyen, Y. Opoku-Boahen, J. Mann, SM. Gowan, et al. LM. Kelland, MA. Read, S. Neidle. (2000). A novel inhibitor of human telomerase derived from 10H-indolo[3,2-b]quinoline. Bioorg Med Chem Lett. 10(18), pp.2063-2066.

  MA. Brimble, VE. Caprio, AD. Johnston, MH. Sidford (2000). Synthesis of aryl spiroketals related to the papulacandins via allylation of phthalides. Tetrahedron Letters. 41(20), pp.3955-3958.

  A. Baron, V. Caprio, J. Mann (1999). Synthesis of key intermediates for a concise and convergent approach to the marine natural product eleutherobin. Tetrahedron Letters. 40(52), pp.9321-9324.

  V. Caprio, J. Mann (1998). Synthesis of novel chromeno[3,4-b]pyridinones. Journal of the Chemical Society, Perkin Transactions 1. pp.3151-3156.

• Chapters in books

  V. Caprio (2008). Pyridines and their benzo derivatives: Reactivity of substituents. In: Comprehensive Heterocyclic Chemistry III. pp.101-169.

  V. Caprio (2004). Ketones: Dialkyl ketones. In: Comprehensive Organic Functional Group Transformations II. pp.135-214.

• Reports

Other distinctions