PUBLICATIONS

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SELECTED PUBLICATIONS:

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Exploring the origins of selectivity in soluble Epoxide Hydrolase from Bacillus megaterium

Serrano-Hervás, E.; Garcia-Borràs, M.*; Osuna, S*. , Org. Biomol. Chem. 2017, accepted for publication.

http://dx.doi.org/10.1039/C7OB01847A

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Exploring the reversal of enantioselectivity on a Zinc-dependent Alcohol Dehydrogenase

Maria-Solano, M. A., Romero-Rivera, A., Osuna, S.*, Org. Biomol. Chem. 201715, 4122 – 4129.

Our article has been selected as HOT, and thus is part of the themed collections: 2017 Hot Articles in Organic and Biomolecular Chemistry

http://pubs.rsc.org/en/content/articlelanding/2017/ob/c7ob00482f#!divAbstract

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figure2_chemcomm_fortalk_notext-copiaComputational tools for the evaluation of laboratory-engineered biocatalysts

Romero-Rivera, A., Garcia-Borràs, M., Osuna, S.*, Chem. Commun. 2017, 53, 284-297.

http://pubs.rsc.org/en/


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TOC_accountsMolecular Dynamics Explorations of Active Site Structure in Designed and Evolved Enzymes

Osuna, S; Jiménez-Osés, G.; Noey, L.; Houk, K. N. Acc. Chem. Res. 2015, 48, 1080-1089.

http://pubs.acs.org/doi/abs/10.1021/ar500452qlines

TOC_v2The Role of Distant Mutations and Allosteric Regulation on LovD Active Site Dynamics

Jiménez-Osés, G.†; Osuna, S.†; Gao, X.†; Sawaya, M.R.; Gilson, L.; Collier, S. J.; Huisman, G.H.; Yeates, T.O.; Tang, Y.; Houk, K.N. Nature Chem. Biol. 2014, 10,431-436 (†: The authors have equally contributed to the work). http://www.nature.com/nchembio/journal/v10/n6/full/nchembio.1503.htmllines

FULL LIST OF PUBLICATIONS:

59. Serrano-Hervás, E.; Garcia-Borràs, M.*; Osuna, S*. Exploring the origins of selectivity in soluble Epoxide Hydrolase from Bacillus megaterium, Org. Biomol. Chem. 2017, accepted for publication. 

58. López-Andarias, J.; H. Mejías, S.; Sakurai, T.; Matsuda, W.; Seki, S.; Feixas, F.; Osuna, S.; Atienza, C.; Martín, N.; Cortajarena, A. L. Toward bioelectronic nanomaterials: photoconductivity in protein-porphyrin hybrids wrapped around SWCNT, Adv. Funct. Mat. 2017, accepted for publication.  

57. Vidal, S.; Izquierdo, M.; Alom, S.; Garcia-Borràs, M.; Filippone, S.; Osuna, S.; Solà, M.; Whitby, R. J.; Martín, N. Effect of incarcerated HF on the exohedral chemical reactivity of HF@C60, Chem. Commun., 201753, 10993

56. Li, G.; Maria-Solano, M. A., Romero-Rivera, A., Osuna, S.*, Reetz, M.* Inducing High Activity of a Thermophilic Enzyme At Ambient Temperature by Directed Evolution, Chem. Commun. 2017, 53, 9454- 9457

55. Garcia-Borràs, M.*, Luis, J. M., Solà, M.*, Osuna, S.* The Key Role of aromaticity in the structure and reactivity of C60 and endohedral metallofullerenes,‎ Inorg. Chim. Acta 2017, special Issue dedicated to Prof. Echegoyen, accepted for publication.

54. Maria-Solano, M. A., Romero-Rivera, A., Osuna, S.*, Exploring the reversal of enantioselectivity on a Zinc-dependent Alcohol Dehydrogenase, Org. Biomol. Chem. 201715, 4122 – 4129. 

53. Garcia-Borràs, M., Osuna, S., Luis, J. M., Solà, M.,Rationalizing the Relative Abundances of Trimetallic Nitride Template-based Endohedral Metallofullerenes from Aromaticity Measures,  Chem. Commun. 2017, 53, 4140 – 4143.

52. Romero-Rivera, A., Garcia-Borràs, M., Osuna, S.* Computational tools for the evaluation of laboratory-engineered biocatalysts, Chem. Commun. 2017, 53, 284-297.

51. Li, Y., Osuna, S., Garcia-Borràs, M., Qi, X., Liu, S., Houk, K. N., Lan, Y. Reactivity of Single-Walled Carbon Nanotubes in the Diels–Alder Cycloaddition Reaction: Distortion–Interaction Analysis along the Reaction Pathway, Chem. Eur. J. 2016, 22, 12819-12824.

50. Martínez, J. P.; Garcia-Borràs, M.; Osuna, S.; Poater, J.; Bickelhaupt, F. M.; Solà, M. Reaction Mechanism and Regioselectivity of the Bingel-Hirsch Addition of Dimethyl Bromomalonate to La@C2v-C82, Chem. Eur. J. 201622, 5953-5962.

49. Garcia-Borràs, M.; Cerón, M. R.; Osuna, S.; Izquierdo, M.; Luis, J. M.; Echegoyen, L.; Solà, M. The Regioselectivity of Bingel-Hirsch Cycloadditions on IPR Endohedral Metallofullerenes, Angew. Chem. Int. Ed. 2016, 55, 2374-2377.

48. Martínez, J. P.; Langa, F.; Bickelhaupt, F. M.; Osuna, S.; Solà, M. (4+2) and (2+2) Cycloadditions of Benzyne to C60 and Zig-Zag Single-Walled Carbon Nanotubes: The Effect of Curvature, J. Phys. Chem. C 2016, 120, 1716-1726

47. Noey, E. L.; Tibrewal, N.; Jiménez-Osés, G.; Osuna, S.; Park, J.; Bond, C.; Cascio, D.; Liang, J.; Zhang, X.; Huisman, G.; Tang, Y.; Houk, K. N. Origins of Stereoselectivity in Evolved Ketoredutases, Proc. Natl. Acad. Sci. USA 2015, 112, E7065-E7072.

46. Cerón, M. R.; Izquierdo, M.; Garcia-Borràs, M.; Lee, S. S.; Stevenson, S.; Osuna, S.*; Echegoyen, L.* Bis-1,3-Dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih-C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control, J. Am. Chem. Soc. 2015, 137, 11775–11782.

45. Osuna, S; Jiménez-Osés, G.; Noey, L.; Houk, K. N. Molecular Dynamics Explorations of Active Site Structure in Designed and Evolved Enzymes, Acc. Chem. Res. 2015, 48, 1080-1089.

44. Maroto, E. E.; Mateos, J.; Garcia-Borràs, M.; Osuna, S.*; Filippone,S.*; Herranz, M. A.; Murata, Y.; Solà, M.*; Martín, N.* Enantiospecific cis-trans Isomerization in Chiral Fulleropyrrolidines: H-Bonding assistance in the carbanion stabilization in H2O@C60 J. Am. Chem. Soc. 2015137, 1190-1197.

43. Martínez, J. P.; Osuna, S.; Solà, M.; Voityuk, A. Extent of charge separation and exciton delocalization for electronically excited states in a triphenylamine C60 donor-acceptor conjugate: a combined molecular dynamics and TD-DFT study, Theor. Chem. Acc. 2015, 134, 1.

42. Aroua, S.; Garcia-Borràs, M.; Bölter, M.; Osuna, S.*; Yamakoshi, Y.* Endohedral Metal-induced Regioselective Formation of Bis- Prato Adduct of Y3N@Ih-C80 and Gd3N@Ih-C80 J. Am. Chem. Soc. 2015, 137, 58–61.

41. Beltran-Alvarez, P.; Feixas, F.;† Osuna, S.;† Díaz-Hernández, R.; Brugada, R.; Pagans, S. Interplay between R513 methylation and S516 phosphorylation of the cardiac voltage-gated sodium channel, Amino Acids 2015, 47, 429-434. (†: the authors have equally contributed)

40. García-Simón,C.; Garcia-Borràs, M.; Gómez, L.; Parella, T.; Osuna, S.; Juanhuix, J.; Imaz, I.; Maspoch, D.; Costas, M.; Ribas, X., Sponge-like molecular cage for purification of fullerenes, Nature Commun. 2014, 5, art. nr. 5557.

39. Aroua, S.; Garcia-Borràs, M.; Osuna, S.;* Yamakoshi, Y.*, Essential Factors for Control of the Equilibrium in the Reversible Rearrangement of M3N@Ih-C80, Chem. Eur. J. 2014, 20, 14032-14039.

38. Cao, Y.; Liang, Y.; Zhang, L.; Osuna, S.; Hoyt, A.-L. M.; Briseno, A. L.; Houk, K. N. Why bistetracenes are much less reactive than pentacenes in Diels-Alder reactions with fullerenes, J. Am. Chem. Soc. 2014, 136, 10743-10751.

37. Garcia-Borràs, M.; Osuna, S.*; Swart, M.; Luis, J. M.*; Solà, M.*, The role of aromaticity in the molecular structure and reactivity of (endohedral metallo)fullerenes,  Chem. Soc. Rev. 2014, 43, 5089-5105.

36. Jiménez-Osés, G.†; Osuna, S.†; Gao, X.†; Sawaya, M.R.; Gilson, L.; Collier, S. J.; Huisman, G.H.; Yeates, T.O.; Tang, Y.; Houk, K.N. The Role of Distant Mutations and Allosteric Regulation on Active Site Dynamics and Catalysis, Nature Chem. Biol. 2014, 10, 431-436. (†: The authors have equally contributed to the work)

35. Parker, M. F. L.; Osuna, S.; Bollot, G.; Vaddypally, S.; Zdilla, M. J.; Houk, K. N.; Schafmeister, C. E. Acceleration of an Aromatic Claisen Rearrangement via a Designed Spiroligozyme Catalyst that Mimics the Ketosteroid Isomerase Catalytic Dyad, J. Am. Chem. Soc. 2014, 136, 3817-3827.

34. Cao, Y.; Osuna, S.; Liang, Y.; Haddon, R.; Houk, K. N.; Diels-Alder Reactions of Graphene: Computational Predictions of Products and Sites of Reaction, J. Am. Chem. Soc. 2013, 135, 17643–17649.

33. Osuna, S.*; Dermenci, A.; Miller, S. J.; Houk, K. N.* The Roles of Counter-ion and Water in a Stereoselective Cysteine-Catalyzed Rauhut-Currier Reaction: A Challenge for Computational Chemistry, Chem. Eur. J. 2013, 19, 14245-14253.

32. Garcia-Borràs, M.; Osuna, S.; Luis, J. M.; Swart, M.; Solà, M. A Complete Guide on the Influence of Metal Clusters in the Diels-Alder Regioselectivity of Ih-C80 Endohedral Metallofullerenes, Chem. Eur. J. 2013, 19, 14931-14940.

31. Garcia-Borràs, M.; Osuna, S.; Swart, M.; Luis, J.M.; Solà, M. Aromaticity as Driving Force for the Stability of non-IPR Endohedral Metallofullerene Bingel-Hirsch Adducts, Chem. Commun. 2013, 49, 8767-8769.

30. Fang, L.; Liu, P.; Sveinbjornsson,B. R.; Atahan-Evrenk, S.; Vandewal, K.; Osuna, S.; Jiménez-Osés, G.; Shrestha, S.; Giri, G.; Wei, P.; Salleo, A.; Aspuru-Guzik, A.; Grubbs, R. H.; Houk, K. N.; Bao, Z. Confined Organization of Fullerene Units Along High Polymer Chains, J. Mater. Chem. C 2013, 1, 5747-5755.

29. Garcia-Borràs, M.; Osuna, S.; Swart, M.; Luis, J. M.; Solà, M. Maximum Aromaticity as a Guiding Principle for the Most Suitable Hosting Cages in Endohedral Metallofullerenes, Angew. Chem. Int. Ed. 2013, 52, 9275-9278.

28. Bian, S.; Scott, A. M.; Cao, Y.; Liang, Y.; Osuna, S.; Houk, K. N.; Braunschweig, A. B. Covalently Patterned Graphene Surfaces by a Force-Accelerated Diels-Alder Reaction, J. Am. Chem. Soc. 2013, 135, 9240-9243.

27. Wang, H.; Mei, J.; Liu, P.; Schmidt, K.; Jiménez-Osés, G.; Osuna, S.; Fang, L.;Tassone, C. J.; Zoombelt, A. P.; Sokolov, A. N.; Houk, K. N.; Toney, M. F.; Bao, Z. Scalable and Selective Dispersion of Semiconducting Arc-Discharged Carbon Nanotubes by Dithiafulvalene/Thiophene Copolymers for Thin Film Transistors, ACS nano 2013, 7, 2659-2668.

26. Osuna, S.; Kim, S.; Bollot, G.; Houk, K. N. Aromatic Claisen Rearrangements of O-prenylated Tyrosine and Model Prenyl Aryl Ethers: Computational Study of the Role of Water on Acceleration of Claisen rearrangements, Eur. J. Org. Chem. 2013, 2823-2831.

25. Garcia-Borràs, M.; Osuna, S.; Swart, M.; Luis, J. M.; Solà, M. Electrochemical Control of the Regioselectivity in the Exohedral Functionalization of C60: the Role of Aromaticity, Chem. Commun. 2013, 49, 1220-1222.

24. García-Simón, C.; Garcia-Borràs, M.; Gómez, L.; Garcia-Bosch, I.; Osuna, S.; Swart, M.; Luis, J. M.; Rovira, C.; Almeida, M.; Imaz, I.; Maspoch, D.; Costas, M.; Ribas, X. Self-Assembled Tetragonal Prismatic Molecular Cage Highly Selective for Anionic π Guests, Chem. Eur. J. 2013, 19, 1445–1456.

23. Osuna, S.; Valencia, R.; Rodríguez-Fortea, A.; Swart, M.; Solà, M.; Poblet, J. M. Full Exploration of the Diels–Alder Cycloaddition on Metallofullerenes M3N@C80 (M=Sc, Lu, Gd): The D5h versus Ih Isomer and the Influence of the Metal Cluster, Chem. Eur. J. 2012, 18, 8944–8956.

22. Garcia-Borràs, M.; Osuna, S.; Luis, J. M.; Swart, M.; Solà, M. The Exohedral Diels–Alder Reactivity of the Titanium Carbide Endohedral Metallofullerene Ti2C2@D3h-C78: Comparison with D3h-C78 and M3N@D3h-C78 (M=Sc and Y) Reactivity, Chem. Eur. J. 2012, 18, 7141–7154.

21. Garcia-Borràs, M.; Romero-Rivera, A.; Osuna, S.; Luis, J. M.; Swart, M.; Solà, M. The Frozen Cage Model: A Computationally Low-Cost Tool for Predicting the Exohedral Regioselectivity of Cycloaddition Reactions Involving Endohedral Metallofullerenes, J. Chem. Theory Comput. 2012, 8, 1671–1683.

20. Osuna, S.; Rodríguez-Fortea, A.; Poblet, J. M.; Solà, M.; Swart, M. Product Formation in the Prato Reaction on Sc3N@D5h-C80: Preference for [5,6]-bonds, and not Pyracylenic Bonds, Chem. Commun. 2012, 48, 2486-2488.

19. Osuna, S.; Swart, M; Solà, M. Dispersion Corrections Are Essential for the Study of Chemical Reactivity in Fullerenes, J. Phys. Chem. A 2011, 115, 3491-3496.

18. Osuna, S.; Swart, M.; Solà, M. The Reactivity of Endohedral Fullerenes. What Can Be Learnt from Computational Studies? Phys. Chem. Chem. Phys., 2011, 13, 3585-3603.

17. Osuna, S.; Torrent-Sucarrat, M.; Solà, M.; Geerlings, P.; Ewels, C. P.; Van Lier, G. Reaction Mechanisms for Graphene and Carbon Nanotube Fluorination, J. Phys. Chem. C 2010, 114, 3340–3345.

16. Osuna, S.; Swart, M.; Solà, M., On the Mechanism of the Superoxide Dismutation Involving Fullerene Derivatives. Chem. Eur. J. 2010, 16, 3207-3214.

15. Dachs, A.; Osuna, S.; Roglans, A.; Solà, M. A Density Functional Theory Study of the [2+2+2] Cyclotrimerization of Acetylene Catalyzed by the Wilkinson’s Catalyst, RhCl3(PPh3)3. The effect of replacing PPh3 for PH3, Organometallics 2010, 29, 562-569.

14. Izquierdo, M.; Osuna, S.; Filippone, S.; Martín-Domenech, A. ; Solà, M.; Martín, N. On the Regioselective Intramolecular Nucleophilic Addition of Thiols to C60. Eur. J. Org. Chem. 2009, 6231-6238.

13. Delgado, J. L.; Osuna, S.; Bouit, P. A.; Martínez-Álvarez, R.; Espíldora, E.; Solà, M.; Martín, N. Competitive Retro-Cycloaddition Reaction in Fullerene Dimers connected through pyrrolidino-pyrazolino Rings, J. Org. Chem. 2009, 74, 8174-8180.

12. Izquierdo, M.; Osuna, S.; Filippone, S.; Martín-Domenech, A.; Solà, M.; Martín, N. Regioselective Intramolecular Nucleophilic Addition of Alcohols to C60: One-step Formation of a cis-1 Bicyclic-fused Fullerene, J. Org. Chem. 2009, 74, 6253-6259.

11. Osuna, S.; Swart, M.; Baerends, E. J.; Bickelhaupt, F. M.; Solà, M., Homolytic versus Heterolytic Dissociation in Diatomic Alkalimetal Halides. The effect of microsolvation. Chem. Phys. Chem. 2009, 10, 2955-2967.

10. Osuna, S.; Swart, M.; Solà, M., Reactivity and Regioselectivity of Noble Gas Endohedral Fullerenes Ng2@C60 (Ng = He–Xe). Chem. Eur. J. 2009, 15, 13111-13123.

9. Osuna, S.; Houk, K. N., Cycloaddition Reactions of Butadiene and 1,3-dipoles to Curved Arenes, Fullerenes, and Nanotubes: Theoretical Evaluation of the Role of Distortion Energies on Activation Barriers. Chem. Eur. J. 2009, 15, 13219-13231.

8. Osuna, S.*; Torrent-Sucarrat, M.; Ewels, C. P.; Solà, M.; Geerlings, P.; Van Lier, G., Local Aromaticity of Pristine and Fluorinated Carbon Nanotubes. J. Nanosci. Nanotech. 2009, 9, 6078-6083.

7. Osuna, S.; Morera, J.; Cases, M.; Morokuma, K.; Solà, M., The Diels-Alder Reaction between Cyclopentadiene and C60: An Analysis of the Performance of the ONIOM Method for the Study of Chemical Reactivity in Fullerenes and Nanotubes. J. Phys. Chem. A 2009, 113, 9721-9726.

6. Dachs, A.; Torrent, A.; Roglans, A.; Parella, T.; Osuna, S.; Solà, M., Rhodium(I)-Catalysed Intramolecular [2+2+2] Cyclotrimerisations of 15-, 20- and 25-Membered Azamacrocycles: Experimental and Theoretical Mechanistic Studies. Chem. Eur. J. 2009, 15, 5289-5300.

5. Izquierdo, M.; Osuna, S.; Filippone, S.; Martín-Domenech, A.; Solà, M.; Martín, N., H-Bond-Assisted Regioselective (cis-1) Intramolecular Nucleophilic Addition of the Hydroxyl Group to [60]Fullerene. J. Org. Chem. 2009, 74, 1480-1487.

4. Osuna, S.; Swart, M.; Solà, M., The Diels Alder Reaction on the Endohedral Y3N@C78: The Importance of the Fullerene Strain Energy. J. Am. Chem. Soc. 2009, 131, 129-139.

3. Filippone, S. §; Barroso, M. I.; Martín-Domenech, A.; Osuna, S. §; Solà, M.; Martín, N., On the mechanism of the thermal retrocycloaddition of pyrrolidinofullerenes (retro-Prato reaction). Chem. Eur. J. 2008, 14, 5198-5206. (§: The authors contributed equally to the work: Correction. Chem. Eur. J. 2008, 14, 5709).

2. Osuna, S.; Swart, M.; Campanera, J.; Poblet, J.; Solà, M., Chemical Reactivity of D3h C78 (Metallo) Fullerene: Regioselectivity Changes Induced by Sc3N Encapsulation. J. Am. Chem. Soc. 2008, 130, 6206-6214.

1. Osuna, S.; Poater, J.; Bofill, J. M.; Alemany, P.; Solà, M., Are nucleus-independent (NICS) and 1H NMR chemical shifts good indicators of aromaticity in p-stacked polyfluorenes? Chem. Phys. Lett. 2006, 428, 191-195.

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