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Vibrational Circular Dichroism versus Optical Rotation Dispersion and Electronic Circular Dichroism for diastereomers: the stereochemistry of 3-(1′-hydroxyethyl)-1-(3′-phenylpropanoyl)-azetidin-2-one

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Gussem, Ewoud De Bultinck, Patrick Feledziak, Marion [UCL] Marchand-Brynaert, Jacqueline [UCL] Stevens, Christian V. Herrebout, Wouter

The absolute configuration of a relatively large and conformationally flexible chiral compound, 3-(1′-hydroxyethyl)-1-(3′-phenylpropanoyl) -azetidin-2-one, is determined using Vibrational Circular Dichroism (VCD) spectroscopy, Optical Rotation Dispersion (ORD) and Electronic Circular Dichroism (ECD). To that end a state of the art experimental VCD spectrum is compared to a theoretical spectrum and the absolute configuration is assigned. ORD and ECD are also used in the assignment to investigate the complementarity of the three techniques. VCD spectroscopy is found to have important advantages over ORD and ECD for diastereomers. The concept of robust modes is applied to this conformationally flexible molecule, showing that its use is limited for such large and flexible molecules.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 2012
Language Anglais
Journal information "Physical Chemistry Chemical Physics" - Vol. 14, no.24, p. 8562 (2012)
Peer reviewed yes
Publisher Royal Society of Chemistry ((United Kingdom) [S.l.])
issn 1463-9076
e-issn 1463-9084
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Links
  1. Hutt A. G., O'Grady J., Drug chirality: a consideration of the significance of the stereochemistry of antimicrobial agents, 10.1093/jac/37.1.7
  2. Allenmark Stig, Gawronski Jacek, Determination of absolute configuration—An overview related to this Special Issue, 10.1002/chir.20524
  3. Magyarfalvi Gábor, Tarczay György, Vass Elemér, Vibrational circular dichroism, 10.1002/wcms.39
  4. Barron Laurence D., Buckingham A. David, Vibrational optical activity, 10.1016/j.cplett.2010.03.090
  5. Flack H. D., Bernardinelli G., Absolute structure and absolute configuration, 10.1107/s0108767399004262
  6. Flack H. D., Bernardinelli G., The use of X-ray crystallography to determine absolute configuration, 10.1002/chir.20473
  7. Stephens Philip J., Theory of vibrational circular dichroism, 10.1021/j100251a006
  8. Stephens P. J., Devlin F. J., Chabalowski C. F., Frisch M. J., Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields, 10.1021/j100096a001
  9. Stephens P. J., Devlin F. J., Cheeseman J. R., Frisch M. J., Calculation of Optical Rotation Using Density Functional Theory, 10.1021/jp0105138
  10. Muñoz Marcelo A., Muñoz Orlando, Joseph-Nathan Pedro, Absolute Configuration of Natural Diastereoisomers of 6β-Hydroxyhyoscyamine by Vibrational Circular Dichroism, 10.1021/np060133j
  11. Muñoz Marcelo A., Muñoz Orlando, Joseph-Nathan Pedro, Absolute configuration determination and conformational analysis of (−)-(3S,6S)-3α,6β-diacetoxytropane using vibrational circular dichroism and DFT techniques, 10.1002/chir.20734
  12. Muñoz Marcelo A., Chamy Cristina, Carrasco Alvaro, Rovirosa Juana, San Martín Aurelio, Joseph-Nathan Pedro, Diastereoisomeric assignment in a pacifenol derivative using vibrational circular dichroism, 10.1002/chir.20801
  13. Debie Elke, Kuppens Tom, Vandyck Koen, Van der Eycken Johan, Van Der Veken Benjamin, Herrebout Wouter, Bultinck Patrick, Vibrational circular dichroism DFT study on bicyclo[3.3.0]octane derivatives, 10.1016/j.tetasy.2006.11.046
  14. Yang, Chirality, 22, 734 (2010)
  15. Kuppens T., Vandyck K., Van der Eycken J., Herrebout W., van der Veken B. J., Bultinck P., Determination of the Absolute Configuration of Threeas-Hydrindacene Compounds by Vibrational Circular Dichroism, 10.1021/jo050666h
  16. Longhi Giovanna, Abbate Sergio, Scafato Patrizia, Rosini Carlo, A vibrational circular dichroism approach to the determination of the absolute configuration of flexible and transparent molecules: fluorenone ketals of 1,n-diols, 10.1039/b913213a
  17. Cherblanc Fanny, Lo Ya-Pei, De Gussem Ewoud, Alcazar-Fuoli Laura, Bignell Elaine, He Yanan, Chapman-Rothe Nadine, Bultinck Patrick, Herrebout Wouter A., Brown Robert, Rzepa Henry S., Fuchter Matthew J., On the Determination of the Stereochemistry of Semisynthetic Natural Product Analogues using Chiroptical Spectroscopy: Desulfurization of Epidithiodioxopiperazine Fungal Metabolites, 10.1002/chem.201101129
  18. Gordillo-román Bárbara, Camacho-ruiz Jorge, Bucio María A., Joseph-Nathan Pedro, Chiral recognition of diastereomeric 6-cedrols by vibrational circular dichroism, 10.1002/chir.21036
  19. Batista João M., Batista Andrea N. L., Mota Jonas S., Cass Quezia B., Kato Massuo J., Bolzani Vanderlan S., Freedman Teresa B., López Silvia N., Furlan Maysa, Nafie Laurence A., Structure Elucidation and Absolute Stereochemistry of Isomeric Monoterpene Chromane Esters, 10.1021/jo1025089
  20. Batista João Marcos, Batista Andrea N.L., Rinaldo Daniel, Vilegas Wagner, Cass Quezia B., Bolzani Vanderlan S., Kato Massuo J., López Silvia N., Furlan Maysa, Nafie Laurence A., Absolute configuration reassignment of two chromanes from Peperomia obtusifolia (Piperaceae) using VCD and DFT calculations, 10.1016/j.tetasy.2010.09.004
  21. Debie Elke, Jaspers Lize, Bultinck Patrick, Herrebout Wouter, Veken Benjamin Van Der, Induced solvent chirality: A VCD study of camphor in CDCl3, 10.1016/j.cplett.2007.11.064
  22. Debie, Phys. Chem. Chem. Phys., 3948 (2008)
  23. Nicu Valentin Paul, Baerends Evert Jan, Effects of Complex Formation on Vibrational Circular Dichroism Spectra, 10.1021/jp710201q
  24. Góbi Sándor, Magyarfalvi Gábor, Reliability of computed signs and intensities for vibrational circular dichroism spectra, 10.1039/c1cp21645g
  25. Feledziak Marion, Michaux Catherine, Urbach Allan, Labar Geoffray, Muccioli Giulio G., Lambert Didier M., Marchand-Brynaert Jacqueline, β-Lactams Derived from a Carbapenem Chiron Are Selective Inhibitors of Human Fatty Acid Amide Hydrolase versus Human Monoacylglycerol Lipase, 10.1021/jm9008532
  26. Nafie Laurence A., Dual Polarization Modulation: A Real-Time, Spectral-Multiplex Separation of Circular Dichroism from Linear Birefringence Spectral Intensities, 10.1366/0003702001948664
  27. Halgren Thomas A., Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94, 10.1002/(sici)1096-987x(199604)17:5/6<490::aid-jcc1>3.0.co;2-p
  28. Halgren Thomas A., MMFF VII. Characterization of MMFF94, MMFF94s, and other widely available force fields for conformational energies and for intermolecular-interaction energies and geometries, 10.1002/(sici)1096-987x(199905)20:7<730::aid-jcc8>3.0.co;2-t
  29. Clark Matthew, Cramer Richard D., Van Opdenbosch Nicole, Validation of the general purpose tripos 5.2 force field, 10.1002/jcc.540100804
  30. Goto Hitoshi, Osawa Eiji, Corner flapping: a simple and fast algorithm for exhaustive generation of ring conformations, 10.1021/ja00206a046
  31. Gotō Hitoshi, Ōsawa Eiji, An efficient algorithm for searching low-energy conformers of cyclic and acyclic molecules, 10.1039/p29930000187
  32. Becke Axel D., A new mixing of Hartree–Fock and local density‐functional theories, 10.1063/1.464304
  33. Lee Chengteh, Yang Weitao, Parr Robert G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, 10.1103/physrevb.37.785
  34. Dunning Thom H., Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen, 10.1063/1.456153
  35. Tomasi Jacopo, Cammi Roberto, Mennucci Benedetta, Medium effects on the properties of chemical systems: An overview of recent formulations in the polarizable continuum model (PCM), 10.1002/(sici)1097-461x(1999)75:4/5<783::aid-qua44>3.0.co;2-g
  36. Tomasi Jacopo, Mennucci Benedetta, Cammi Roberto, Quantum Mechanical Continuum Solvation Models, 10.1021/cr9904009
  37. Schellman John A., Circular dichroism and optical rotation, 10.1021/cr60295a004
  38. Stephens, Chirality, 22, 229 (2010)
  39. Nicu Valentin Paul, Debie Elke, Herrebout Wouter, Van der Veken Benjamin, Bultinck Patrick, Baerends Evert Jan, A VCD robust mode analysis of induced chirality: The case of pulegone in chloroform, 10.1002/chir.20817
  40. Nicu Valentin Paul, Baerends Evert Jan, On the origin dependence of the angle made by the electric and magnetic vibrational transition dipole moment vectors, 10.1039/c1cp21442j
  41. Polavarapu Prasad L., Scalmani Giovanni, Hawkins Edward K., Rizzo Carmelo, Jeirath Neha, Ibnusaud Ibrahim, Habel Deenamma, Nair Divya Sadasivan, Haleema Simimole, Importance of Solvation in Understanding the Chiroptical Spectra of Natural Products in Solution Phase: Garcinia Acid Dimethyl Ester, 10.1021/np100512w
  42. Finley J.W., Stephens P.J., Density functional theory calculations of molecular structures and harmonic vibrational frequencies using hybrid density functionals, 10.1016/0166-1280(95)04333-8
  43. Debie Elke, De Gussem Ewoud, Dukor Rina K., Herrebout Wouter, Nafie Laurence A., Bultinck Patrick, A Confidence Level Algorithm for the Determination of Absolute Configuration Using Vibrational Circular Dichroism or Raman Optical Activity, 10.1002/cphc.201100050
  44. Stephens P. J., Devlin F. J., Gasparrini F., Ciogli A., Spinelli D., Cosimelli B., Determination of the Absolute Configuration of a Chiral Oxadiazol-3-one Calcium Channel Blocker, Resolved Using Chiral Chromatography, via Concerted Density Functional Theory Calculations of Its Vibrational Circular Dichroism, Electronic Circular Dichroism, and Optical Rotation, 10.1021/jo070302k
  45. Stephens P. J., Aamouche A., Devlin F. J., Superchi S., Donnoli M. I., Rosini C., Determination of Absolute Configuration Using Vibrational Circular Dichroism Spectroscopy:  The Chiral Sulfoxide 1-(2-methylnaphthyl) Methyl Sulfoxide, 10.1021/jo001403k
  46. Stephens P.J, Devlin F.J, Cheeseman J.R, Frisch M.J, Mennucci B, Tomasi J, Prediction of optical rotation using density functional theory: 6,8-dioxabicyclo[3.2.1]octanes, 10.1016/s0957-4166(00)00178-6
  47. Kuppens Tom, Herrebout Wouter, Van Der Veken Benjamin, Corens David, De Groot Alex, Doyon Julien, Van Lommen Guy, Bultinck Patrick, Elucidation of the absolute configuration of JNJ-27553292, a CCR2 receptor antagonist, by vibrational circular dichroism analysis of two precursors, 10.1002/chir.20297
  48. Kuppens T., Langenaeker W., Tollenaere J. P., Bultinck P., Determination of the Stereochemistry of 3-Hydroxymethyl-2,3-dihydro-[1,4]dioxino[2,3-b]- pyridine by Vibrational Circular Dichroism and the Effect of DFT Integration Grids, 10.1021/jp021822g
  49. Nicu Valentin Paul, Baerends Evert Jan, Robust normal modes in vibrational circular dichroism spectra, 10.1039/b823558a
  50. POLAVARAPU PRASAD, Ab initio molecular optical rotations and absolute configurations, 10.1080/00268979709482744
  51. Polavarapu Prasad L., Zhao Chunxia, A comparison of ab initio optical rotations obtained with static and dynamic methods, 10.1016/s0009-2614(98)01009-4
  52. Caldwell Dennis J., Eyring Henry, Optical Rotation, 10.1103/revmodphys.35.577
  53. Kondru Rama K., Wipf Peter, Beratan David N., Structural and Conformational Dependence of Optical Rotation Angles, 10.1021/jp990697e
  54. Wood William W., Fickett Wildon, Kirkwood John G., The Absolute Configuration of Optically Active Molecules, 10.1063/1.1700491
  55. Karunakaran Venugopal, Denisov Ilia, Sligar Stephen G., Champion Paul M., Investigation of the Low Frequency Dynamics of Heme Proteins: Native and Mutant Cytochrome P450camand Redox Partner Complexes, 10.1021/jp112298y
Bibliographic reference Gussem, Ewoud De ; Bultinck, Patrick ; Feledziak, Marion ; Marchand-Brynaert, Jacqueline ; Stevens, Christian V. ; et. al. Vibrational Circular Dichroism versus Optical Rotation Dispersion and Electronic Circular Dichroism for diastereomers: the stereochemistry of 3-(1′-hydroxyethyl)-1-(3′-phenylpropanoyl)-azetidin-2-one. In: Physical Chemistry Chemical Physics, Vol. 14, no.24, p. 8562 (2012)
Permanent URL http://hdl.handle.net/2078.1/124639