Nuno Manuel Xavier

 

Researcher at Centro de Química Estrutural (CQE-Ciências)

    Faculty of Sciences, University of Lisbon (FCUL)

    Member of the Carbohydrate Chemistry Group of CQE-Ciências

 

b. 2. Nov. 1982, Vila Real, Portugal

 

ORCID ID: 0000-0001-8739-8768

Affiliation: Centro de Química Estrutural, Faculdade de Ciências, Universidade de Lisboa, Ed. C8, 5º Piso, Campo Grande, 1749-016 Lisboa, Portugal

E-mail: nmxavier@fc.ul.pt

 

Academic Formation

2005 Graduated in Chemistry (Licenciatura em Química) − FCUL, University of Lisbon

Sept. 2007 to Dec. 2007 Visiting Research Student at the University of Hamburg (Germany), Institute of Organic Chemistry (advisor: Prof. Dr. Joachim Thiem).

May 2011 Ph. D. degree in Chemistry (Organic Chemistry) from the University of Lisbon (advisor: Prof. Dr. Amélia P. Rauter) and in  Chemistry (Speciality Chemistry) from the National Institute of Applied Sciences of Lyon (INSA Lyon, advisor: Dr. Yves Queneau)

Ph.D. Thesis entitled: Synthesis of new sugar derivatives containing an α,β-unsaturated carbonyl system in their structure and biological evaluation.

 

Professional Positions and Membership in Research Units

June 2011 to May 2012  Postdoctoral Research Fellow at the University of Natural Resources and Life Sciences of Vienna (BOKU, Austria), Department of Chemistry (group of Prof. Dr. Paul Kosma).

June 2012 to Dec. 2013  Postdoctoral Research Fellow at FCUL, Center of Chemistry and Biochemistry (group of Prof. Dr. Amélia P. Rauter).

Jan. 2013 to Dec. 2019 Integrated Member of the Center of Chemistry and Biochemistry, FCUL

Jan. 2014 to Dec. 2018  Researcher at FCUL (FCT Investigator), contracted under the 2013 FCT (Portuguese Foundation for Science and Technology) Investigator Programme.

Since Dec. 2017 Integrated Member of Centro de Química Estrutural, FCUL.

Since July 2020 Assistant Researcher at Centro de Química Estrutural, FCUL, selected under the FCT 2018 Individual Call to Scientific Employment Stimulus.

Research Interests 

Organic Chemistry; Medicinal Chemistry; Glycosciences.

Development of innovative, efficient and clean synthetic approaches towards new potentially bioactive sugar derivatives.

A current focus of research is the synthesis and design of nucleoside analogs and nucleotide mimics of potential therapeutic interest as inhibitors of relevant disease-associated enzymes or nucleotide-dependent events.


Teaching

Organic Chemistry I (theoretical-practical courses, 1st year of the Bachelor’s degree programs of Chemistry and of Technological Chemistry)

Medicinal Chemistry of Nucleosides and Nucleotides (1st year of Master in Chemistry and  Master in Chemistry, Health and Nutrition)

Faculty of Sciences, University of Lisbon.

  

Publications

Peer-Reviewed Articles:

30. “Synthesis of triazole‐containing furanosyl nucleoside analogs and their phosphate, phosphoramidate or phoshonate derivatives as potential sugar diphosphate or nucleotide mimetics”, A. Fortuna, P. J. Costa, M. F. M. Piedade, M. C. Oliveira, N. M. Xavier, ChemPlusChem 2020, 85, 1676–1691.

29. “Special Issue "Carbohydrates 2018"”, A. P. Rauter, N. M. Xavier, Pharmaceuticals 2020, 13(1), 5.

28. “Synthesis and biological evaluation of structurally varied 5ʹ-/6ʹ-isonucleosides and theobromine-containing N-isonucleosidyl derivatives”, N. M. Xavier, E. C. de Sousa, M. P. Pereira, A. Loesche, I. Serbian, R. Csuk, M. C. Oliveira, Pharmaceuticals 2019, 12(3), 103.

27. “Novel dodecyl-containing azido and glucuronamide-based nucleosides exhibiting anticancer potential”, N. M. Xavier, R. Goncalves-Pereira, R. Jorda, D. Hendrychová, M. C. Oliveira,  Pure Appl. Chem. 2019, 91, 1085-1105.

26. “Sugar-based bactericides targeting phosphatidylethanolamine-enriched membranes”, C. Dias, J. P. Pais, R. Nunes, M.-T. Blázquez-Sánchez, J. T. Marquês, A. F. Almeida, P. Serra, N. M. Xavier, D. Vila-Viçosa, M. Machuqueiro, A. S. Viana, A. Martins, M. S. Santos, A. Pelerito, R. Dias, R. Tenreiro, M. C. Oliveira, M. Contino, N. Colabufo, R. F. M. Almeida, A. P. Rauter, Nat. Commun. 2018, 9, 4857, 1-12.

25. “Furanosyl nucleoside analogs embodying triazole or theobromine units as potential lead molecules for Alzheimer's disease”, R. G. Pereira, M. P. Pereira, S. G. Serra, A. Loesche, R. Csuk, S. Silvestre, P. J. Costa, M. C. Oliveira, N. M. Xavier, Eur. J. Org. Chem. 2018, 2667-2681. (In Special Issue dedicated to the EurJOC 20th Anniversary)

24. “Synthesis of 1,5-anhydro-D-glycero-D-gluco-heptitol derivatives as potential inhibitors of bacterial heptose biosynthetic pathways”, M. Blaukopf, D. Atamanyuk, N. M. Xavier, V. Gerusz, P. Kosma, Synthesis, 2017, 49, 5320-5334.

23. “Exploitation of new structurally diverse D-glucuronamide-containing N-glycosyl compounds: synthesis and anticancer potential”, N. M. Xavier, A. Porcheron, D. Batista, R. Jorda, E. Řezníčková, V. Kryštof, M. C. Oliveira, Org. Biomol. Chem. 2017, 15, 4667-4680.

22. “Liquid crystalline glycosteroids and acyl steroid glycosides (ASG)", Z. Yang, R. Xu, F. Ali-Rachedi, S. Chambert, N. M. Xavier, L. Soulère, M. Ahmar, G. Mackenzie, E. J. Davis, J. W. Goodby, S. J. Cowling, Y. Queneau, Liq. Cryst, 2017, 44, 2089–2107.

21. “Synthesis and antiproliferative evaluation of novel azido nucleosides and their phosphoramidate derivatives”, N. M. Xavier, R. G. Pereira, R. Jorda, E. Řezníčková, V. Kryštof, M. C. Oliveira, Pure Appl. Chem. 2017, 89(9), 1267–1281.

20. “Synthesis of glucopyranos-6′-yl purine and pyrimidine isonucleosides as potential cholinesterase inhibitors. Access to pyrimidine-linked pseudodisaccharides through Mitsunobu reaction", D. Batista, S.Schwarz,  A. Loesche, R.Csuk, P. J. Costa, M. C. Oliveira, N. M. Xavier, Pure Appl. Chem. 2016, 88(4), 363-379.

19. “Synthesis and evaluation of the biological profile of novel analogs of nucleosides and of potential mimetics of sugar phosphates and nucleotides", N. M. Xavier, S. D. Lucas, R. Jorda, S. Schwarz, A. Loesche, R. Csuk, M. C. Oliveira, Synlett 2015, 26, 2663-2672.

18. “Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation”, R. Xu, F. Ali-Rachedi, N. M. Xavier, S. Chambert, F. Ferkous, Y. Queneau, S. J. Cowling, E. J. Davis, J. W. Goodby, Org. Biomol. Chem. 2015, 13, 783-792.

17. “Enantioselective synthesis in carbohydrate-based drug discovery: imino sugars, alkaloids and macrolide antibiotics”, N. M. Xavier, A. P. Rauter, Curr. Top. Med. Chem., 2014, 14, 1235–1243.

16. “Synthesis of purine nucleosides from D-glucuronic acid derivatives and evaluation of their cholinesterase inhibitory activities”, N. M. Xavier, S. Schwarz, P. D. Vaz, R. Csuk, A. P. Rauter, Eur. J. Org. Chem. 2014, 2014, 2770-2779.

15. “A "natural" approach: synthesis and cytoxicity of monodesmosidic glycyrrhetinic acid glycosides”, S. Schwarz, B. Siewert, N. M. Xavier, A. R. Jesus, A. P. Rauter, R. Csuk, Eur. J. Med. Chem. 2014, 72, 78-83.

14. “Efficient and first regio- and stereoselective direct C-glycosylation of a flavanone catalysed by Pr(OTf)3 under conventional heating or ultrasound irradiation”, R. G. Santos, N. M. Xavier, J. C. Bordado, A. P. Rauter, Eur. J.  Org. Chem. 2013, 2013, 1441–1447.

13. “Environmentally friendly approaches to the synthesis of new antibiotics from sugars" N. M. Xavier, A. P. Rauter, Pure Appl. Chem. 2012, 84, 3, 803–816.

12. “Synthesis of sugars embodying conjugated carbonyl systems and related triazole derivatives from carboxymethyl glycoside lactones. Evaluation of their antimicrobial activity and toxicity”, N. M. Xavier, M. Goulart,  A. Neves,  J. Justino, S. Chambert, A. P. Rauter, Y. Queneau, Bioorg. Med. Chem. 2011, 19, 926−938.

11. “Exploitation of furanoid 5-azido-3-C-branched-chain sugars towards highly functionalized nitrogen-containing carbohydrate derivatives”, N. M. Xavier, Y. Queneau, A. P. Rauter, Eur. J. Org. Chem. 2011, 2011, 713−720.

10. “Carbohydrate-based lactones: synthesis and applications” N. M. Xavier, A. P. Rauter, Y. Queneau, Top. Curr. Chem. 2010, 295, 19–62.

9. “Zeolites and other silicon-based promoters in carbohydrate chemistry”, A. P. Rauter, N. M. Xavier, S. D. Lucas, M. Santos, Adv. Carbohydr. Chem. Biochem. 2010, 63, 29-99.

8. “Furanose C-C-linked γ-lactones: a combined ESI FT-ICR MS and semi-empirical calculations study", P. J. A. Madeira, N. M. Xavier, A. P. Rauter, M. H. Florêncio, J. Mass Spectrom. 2010, 45, 1167–1178.

 7. “Electrospray ionization mass spectrometry analysis of newly synthesized α,β-unsaturated γ-lactones fused to sugars”, P. J. A. Madeira, A. M. Rosa, N. M. Xavier, A. P. Rauter, M. H. Florêncio, Rapid Comm. Mass Spectrom. 2010, 24, 1049–1058.

6. “Zeolites as efficient catalysts for key transformations in carbohydrate chemistry”, N. M. Xavier, S. D. Lucas, A. P. Rauter, J. Mol. Cat. A: Chemical 2009, 305, 84–89.

5. “Synthetic approaches to novel thiosugar scaffolds containing α,β-unsaturated carbonyl groups”, N. M. Xavier, P. J. A. Madeira, M. H. Florêncio, A. P. Rauter, Eur. J. Org. Chem. 2009, 2009, 4983−4991.

4. “Sugars containing α,β-unsaturated carbonyl systems: synthesis and their usefulness as scaffolds in carbohydrate chemistry”, N. M. Xavier, A. P. Rauter, Carbohydr. Res. 2008, 343, 1523–1539.

3. “Synthesis and biological evaluation of sugars containing α,β-unsaturated γ -lactones”, N. M. Xavier, S. Silva, P. J. A. Madeira, M. H. Florêncio, F. V. M. Silva, J. Justino, J. Thiem, A. P. Rauter, Eur. J. Org. Chem. 2008, 2008, 6134–6143.

2. “Easy and stereoselective approach to α,β-unsaturated-γ-lactones fused to pyranoses from furanose scaffolds”, N. M. Xavier, A. P. Rauter, Org. Lett. 2007, 9, 3339−3341.

1. “Acid zeolites as efficient catalysts for O- and S-glycosylation”, A. P. Rauter, T. Almeida, N. M. Xavier, F. Siopa, A. I. Vicente, S. D. Lucas, J. P. Marques, F. Ramôa-Ribeiro,  M. J. Ferreira, M. Guisnet,  J. Mol. Cat. A: Chemical 2007, 275, 206−213.

 

Book Chapters:

8. “Recent developments in synthetic methods for sugar phosphate analogs”, A. Fortuna, N. M. Xavier, In Recent Trends in Carbohydrate Chemistry, Vol. 1, Synthesis, Structure and Function of Carbohydrates  (A. P. Rauter, B. E. Christensen, L. Somsák, P. Kosma, R. Adamo, eds), 2020, chapter 8, pp. 301-329, Elsevier.

7. “Synthesis and biological properties of D-glucuronamide-containing compounds”, N. M Xavier, A. Fortuna, In Elsevier Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (J. Reedijk, ed.), Waltham, MA: Elsevier. 2019, DOI: 10.1016/B978-0-12-409547-2.11098-4.

 6. “Recent advances in the synthesis of N-glycosyl compounds”, N. M. Xavier, R. Nunes, In Advances in Organic Synthesis (Atta-ur-Rahman, ed.), 2018, vol. 10, chapter 3, pp 99-138, Bentham Science Publishers, Sharjah, UAE.  

5. “Recent Advances on Nucleotide Analogs and Mimetics: Synthesis and Biological Properties”, N. M. Xavier, In Elsevier Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (J. Reedijk, ed.), Waltham, MA: Elsevier. 2017, 1-15.

4. “Preparation of a tosylhydrazidyl N-glycosyl derivative of D-glucuronic acid via tosylhydrazone formation and intramolecular ring closure”, N. M. Xavier. In Comprehensive Organic Chemistry Experiments for the Laboratory Classroom (C. A. M. Afonso, R. Franzén, B. Tan, N. R. Candeias, D. Simão, A. Trindade, J. Coelho, eds),  2016, 72, 282-284.  Royal Society of Chemistry, UK.

3. “Triazole-containing carbohydrate mimetics: synthesis and biological applications”, N. M Xavier, S. D. Lucas. In Targets in Heterocyclic Systems: Chemistry and Properties (O. Attanasi, R. Noto, D.Spinelli, eds), 2014, 18, 214-235, Italian Society of Chemistry, Rome, Italy.

2. “Triterpene/steroid glycoconjugates: natural occurrence, synthesis and biological activities”, S. Schwarz, N. M. Xavier, R. Csuk, A. P. Rauter. In Specialist Periodical Reports: Carbohydrate Chemistry (A. P. Rauter, T. Lindhorst, eds.), 2012, 37, 326-373, RSC, London, UK.

1. “Pyranose-fused butenolides: an expedient preparation from furanose synthons”, N. M. Xavier, S. Kopitzki, A. P. Rauter.  In Carbohydrate Chemistry: Proven Synthetic Methods (P. Kováč, ed.), 2011, vol. 1, chapter 15, pp. 137-157, CRC Press, Taylor & Francis, Boca Raton, Florida, USA.

 

Book, Edited

“Carbohydrates 2018”, MDPI, Basel, Switzerland, ISBN 978-3-03928-317-0.

 

Patents:

 2. “(N-Alkylcarbamoyl)methyl enulosides and related pyranoside containing an α,β,γ,δ-unsaturated ester, their preparation and their efficacy as antibacterial agents”, A. P. Rauter, N. M. Xavier, J. Justino, A. Neves, M. Goulart, Y. Queneau.

-WO2012095793-A2, international application nr PCT/IB2012/050125, submitted in 10.01.2012, published in 19.07.2012;

1. “(N-Alquilcarbamoil)metil enulósidos e piranosida relacionada contendo um éster α,β,γ,δ-insaturado, sua preparação e sua eficácia como agentes antibacterianos, A. P. Rauter, J. Justino, N. M. Xavier, A. Neves, M. Goulart.

- PT 105476 A, submitted in 11.01.2011, published in 11.07.2012.

 

Participation in Meetings/Symposia

 ca. 35 Oral Communications (as first author and presenter) in international and national conferences such as:

- XXIV International Carbohydrate Symposium, Oslo, Norway, July 2008

- 7th National Carbohydrate Symposium, Banff, Alberta, Canada, May 2011

- 16h European Carbohydrate Symposium, Sorrento (Naples), Italy, July 2011

- 43rd IUPAC World Chemistry Congress, San Juan, Puerto Rico, August 2011

- 17th European Carbohydrate Symposium, Tel-Aviv, Israel, July 2013

- XXVIII International Carbohydrate Symposium, New Orleans, USA, July 2016

- 46th IUPAC World Chemistry Congress, São Paulo, Brasil, July 2017

recent Invited Lectures at:

-7th Spanish-Portuguese-Japanese Organic Chemistry Symposium, Seville, Spain, June 2015.

-7th EuCheMS Organic Division Young Investigators Workshop (YIW), Aveiro, Portugal, July 2015 (selected as the Portuguese representative).

-11th International Meeting of the Portuguese Carbohydrate Group and 6th Iberian Carbohydrate Meeting, Viseu, Portugal, September 2015.

-3rd Glycobiology World Congress, London, UK, June 2017.

- 12ª Reunião do Grupo dos Glúcidos - Glupor 12 (12th Meeting of the Portuguese Carbohydrate Group), Aveiro, Portugal, September 2017 (Plenary Lecture).

- 29th International Carbohydrate Symposium (ICS 2018), Lisboa, Portugal, July 2018 (Young Scientist Invited Lecture).

ca. 65 Poster communications in international and national conferences.

 

Guest Editor and Reviewer for Scientific Journals

•  Topic Editor for Antibiotics (MDPI, ISSN 2079-6382), since November 2019.

• Guest Associate Editor for Frontiers in Chemistry (ISSN: 2296-2646), section Medicinal and Pharmaceutical Chemistry, since September 2019.

-          Topic Editor of the Research Topic “Carbohydrate-Based Molecules in Medicinal Chemistry” (currently)

• Guest Editor for Pharmaceuticals (MDPI, ISSN 1424-8247)

-          Special Issue "Glycomimetics and Glycoconjugates in Drug Discovery" (currently)

                                         

-          Special issue “Carbohydrates 2018” (2018/2019)

 • Reviewer profile at Publons.

  

Scientific Awards

01/2009  Young Researcher Award, attributed by the scientific committee of the international meeting Carbohydrate as Organic Raw Materials V, Lisboa, Portugal.

01/2010  Scientific Award of the  Groupe Lyonnais des Glycosciences (France).

03/2011  Recipient of the 2011 Alberta Ingenuity Centre for Carbohydrate Science (AICCS) Young Investigator Award (Canada).

05/2011  Recipient of an IUPAC Young Scientists Award from the organizers of the 43rd IUPAC World Chemistry Congress (IUPAC).

07/2012  Recipient of the Poster Award at the 6th Spanish-Portuguese-Japanese Organic Chemistry Symposium, attributed by the Portuguese Chemical Society.

07/2018  Recipient of the J. Pereira da Cruz Innovation Award at the 29th International Carbohydrate Symposium, Lisboa, Portugal.

 

Membership in Scientific Organizations


Since 2013: Member of IUPAC

Since 2015: Member of Sociedade Portuguesa de Química.