Effect of Solvent on the Optical Rotation of Azatryptophan Derivatives.
NMR
azatryptophan derivatives
hydrogen bonding
specific optical rotation
Journal
Magnetic resonance in chemistry : MRC
ISSN: 1097-458X
Titre abrégé: Magn Reson Chem
Pays: England
ID NLM: 9882600
Informations de publication
Date de publication:
24 Sep 2024
24 Sep 2024
Historique:
revised:
19
08
2024
received:
14
06
2024
accepted:
03
09
2024
medline:
24
9
2024
pubmed:
24
9
2024
entrez:
24
9
2024
Statut:
aheadofprint
Résumé
Chirally pure enantiomers of differently protected 7-azatryptophan derivatives (R-3c, S-3c, R-3i, S-3i, R-3m, S-3m, R-3aa, and S-3aa) were synthesized, which showed solvent-dependent optical rotation. The obtained results not only exhibited changes in the values but also showed the variation in sign (- or +) with the different solvents studied. The change in optical rotation value was essentially attributed to the electron-donating property, which can be correlated to the donor number of the solvents. There are two types of hydrogen bonds, intramolecular (i.e., form within the structure) and intermolecular (i.e., form with external groups such as solvents). These hydrogen bonds are responsible for the value and sign variations, and
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Informations de copyright
© 2024 John Wiley & Sons, Ltd.
Références
B. Vig and J. Rautio, “Amino Acid Prodrugs for Oral Delivery: Challenges and Opportunities,” Therapeutic Delivery 2, no. 8 (2011): 959–962.
P. Conti, L. Tamborini, A. Pinto, et al., “Drug Discovery Targeting Amino Acid Racemases,” Chemical Reviews 111 (2011): 6919–6946.
A. Stevenazzi, M. Marchini, G. Sandrone, B. Vergani, and M. Lattanzio, “Amino Acidic Scaffolds Bearing Unnatural Side Chains: An Old Idea Generates New and Versatile Tools for the Life Sciences,” Bioorganic & Medicinal Chemistry Letters 24, no. 23 (2014): 5349–5356.
N. Qvit, J. S. Rubin, T. J. Urban, D. Mochly‐Rosen, and E. R. Gross, “Peptidomimetic Therapeutics: Scientific Approaches and Opportunities,” Drug Discovery Today 22, no. 2 (2017): 454–462.
M. A. T. Blaskovich, “Unusual Amino Acids in Medicinal Chemistry,” Journal of Medicinal Chemistry 59, no. 24 (2016): 10807–10836.
V. D. Filippis, S. D. Boni, E. D. Dea, D. Dalzoppo, C. Grandi, and A. Fontana, “Incorporation of the Fluorescent Amino Acid 7‐Azatryptophan Into the Core Domain 1‐47 of Hirudin as a Probe of Hirudin Folding and Thrombin Recognition,” Protein Science 13, no. 6 (2004): 1489–1502.
S. Lepthien, B. Wiltschi, B. Bolic, and N. Budisa, “In Vivo Engineering of Proteins With Nitrogen‐Containing Tryptophan Analogs,” Applied Microbiology and Biotechnology 73, no. 4 (2006): 740–754.
Y. N. Roshan, V. Devaiah, K. Prakasam, et al., “Synthesis of Differentially Protected Azatryptophan Analogs via Pd2(dba)3/XPhos Catalyzed Negishi Coupling ofN‐Ts Azaindole Halides With Zinc Derivative From Fmoc‐Protected tert‐Butyl (R)‐2‐Amino‐3‐Iodopropanoate,” Journal of Organic Chemistry 85, no. 17 (2020): 11519–11530.
T. Steiner, “The Hydrogen Bond in the Solid State,” Angewandte Chemie, International Edition 41 (2002): 48–76.
C. S. Hudson and J. M. Johnson, “The Isomeric Tetracetates of Xylose, and Observations Regarding the Acetates of Melibiose, Trehalose and Sucrose,” Journal of the American Chemical Society 37 (1915): 2748–2753.
A. Levene and I. Bencowitz, “The Influence of Solvent and of Concentration on the Optical Rotation of the Pentacetates of Glucose and Mannose,” Journal of Biological Chemistry 73 (1927): 679–694.
G. R. Desiraju and T. Steiner, “The Weak Hydrogen Bond In Structural Chemistry and Biology (International Union of Crystallography, Monographs on Crystallography, 9),” Journal of the American Chemical Society 123, no. 1 (2001): 191–192.
S. K. Mishra and N. Suryaprakash, “Organic Fluorine Involved Intramolecular Hydrogen Bonds in the Derivatives of Imides: NMR Evidence Corroborated by DFT Based Theoretical Calculations,” RSC Advances 5 (2015): 86013–86022.
Y. Yong, Y. Z. Yong, Y. P. Yi, et al., “Helical Molecular Duplex Strands: Multiple Hydrogen‐Bond‐Mediated Assembly of Self‐Complementary Oligomeric Hydrazide Derivatives,” Journal of Organic Chemistry 72 (2007): 4936–4946.
F. Reinscheid and U. M. Reinscheid, “Stereochemical Analysis of (+)‐Limonene Using Theoretical and Experimental NMR and Chiroptical Data,” Journal of Molecular Structure 1106 (2016): 141–153.
J. Neugebauer, “Induced Chirality in Achiral Media—How Theory Unravels Mysterious Solvent Effects,” Angewandte Chemie, International Edition 46 (2007): 7738–7740.
G. M. Giovanni, A. Osipov, and G. P. Spada, “A Study of Solvent Effect on the Optical Rotation of Chiral Biaryls,” Journal of Physical Chemistry 95 (1991): 3879–3884.
B. Mennucci, J. Tomasi, R. Cammi, et al., “Polarizable Continuum Model (PCM) Calculations of Solvent Effects on Optical Rotations of Chiral Molecules,” Journal of Physical Chemistry. A 106 (2002): 6102–6113.
A. T. Fischer, R. N. Compton, and R. M. Pagni, “Solvent Effects on the Optical Rotation of (S)‐(−)‐α‐Methylbenzylamine,” Journal of Physical Chemistry. A 110 (2006): 7067–7071.
K. Ruud and R. Zanasi, “The Importance of Molecular Vibrations: The Sign Change of the Optical Rotation of Methyloxirane,” Angewandte Chemie, International Edition 44 (2005): 3594–3596.
F. Lipparini, F. Egidi, C. Cappelli, and V. Barone, “The Optical Rotation of Methyloxirane in Aqueous Solution: A Never Ending Story?” Journal of Chemical Theory and Computation 9 (2013): 1880–1884.
P. Mukhopadhyay, G. Zuber, M. R. Goldsmith, P. Wipf, and D. N. Beratan, “Solvent Effect on Optical Rotation: A Case Study of Methyloxirane in Water,” ChemPhysChem 7 (2006): 2483–2486.
M. C. Caputo, S. Pelloni, and P. Lazzeretti, “Theoretical Prediction of the Optical Rotation of Chiral Molecules in Ordered Media: A Computational Study of (Ra)‐1,3‐Dimethylallene, (2R)‐2‐Methyloxirane, and (2R)‐N‐Methyloxaziridine,” International Journal of Quantum Chemistry 115 (2015): 900–906.
P. Mukhopadhyay, “Theoretical Simulations of Optical Rotation and Raman Optical Activity of Molecules in Solution,” Department of Chemistry in the Graduate School of Duke University, (2008).
J. W. Emsley, “NMR in Anisotropic Systems, Theory,” in Encyclopaedia of Spectroscopy and Spectrometry, vol. 2 (UK: University of Southampton, Elsevier Ltd., 1999), 1521–1527.
P. Lesot, C. Aroulanda, P. Berdague, et al., “Multinuclear NMR in Polypeptide Liquid Crystals: Three Fertile Decades of Methodological Developments and Analytical Challenges,” Progress in Nuclear Magnetic Resonance Spectroscopy 116 (2020): 85–154.
P. Lesot, C. Aroulanda, H. Zimmermann, and Z. Luz, “Enantiotopic Discrimination in the NMR Spectrum of Prochiral Solutes in Chiral Liquid Crystals,” Chemical Society Reviews 44 (2015): 2330–2375.
M. Sarfati, P. Lesot, D. Merlet, and J. Courtieu, “Theoretical and Experimental Aspects of Enantiomeric Differentiation Using Natural Abundance Multinuclear NMR Spectroscopy in Chiral Polypeptide Liquid Crystals,” Chemical Communications 21 (2000): 2069–2081.
T. Williams, R. G. Pitcher, P. Bommer, J. Gutzwiller, and M. Uskokovc, “Diastereomeric Solute‐Solute Interactions of Enantiomers in Achiral Solvents. Nonequivalence of the Nuclear Magnetic Resonance Spectra of Racemic and Optically Active Dihydroquinine,” Journal of the American Chemical Society 91 (1969): 1871–1872.
A. Dobashi, N. Saito, Y. Motoyama, and S. Hara, “Self‐Induced Nonequivalence in the Association of D‐ and L‐Amino Acid Derivatives,” Journal of the American Chemical Society 108 (1986): 307–308.
C. Luchinat and S. Roelens, “Group IVA Organometallic Reagents. 2. Enantiomeric Purity Determination of 1,2‐Diols Through NMR Spectroscopy Without Chiral Auxiliaries,” Journal of the American Chemical Society 108 (1986): 4873–4878.
E. L. Eliel and E. Brunet, “Quantitative Relationship Between Optical Rotation and Conformation,” Journal of Organic Chemistry 56 (1991): 1668–1670.
S. Deguchi, K. Shimatani, T. Tada, K. Nakashima, and T. Yasuda, “Solvent Dependence of Optical Rotation of (S)‐N‐[1‐(2‐Fluorophenyl)‐3,4,6,7‐Tetrahydro‐4‐Oxo‐Pyrrolo‐[3,2,1‐jk][1,4]Benzodiazepine‐3‐Yl]‐1H‐Indole‐2‐Carboxamide,” Journal of Pharmaceutical Sciences 82 (1993): 734–736.
V. K. Vashistha, “Chiral Analysis of Pharmaceuticals Using NMR Spectroscopy: A Review,” Asian The Journal of Organic Chemistry 11 (2022): e202200544.
S. Haghdani, B. H. Hoff, H. Koch, and P. Astrand, “Solvent Effects on Optical Rotation: On the Balance Between Hydrogen Bonding and Shifts in Dihedral Angles,” Journal of Physical Chemistry. A 121 (2017): 4765–4777.
R. D'Cunha and T. D. Crawford, “Modeling Complex Solvent Effects on the Optical Rotation of Chiral Molecules: A Combined Molecular Dynamics and Density Functional Theory Study,” Journal of Physical Chemistry. A 125 (2021): 3095–3108.
M. D. Kundrat and J. Autschbach, “Computational Modeling of the Optical Rotation of Amino Acids: A New Look at an Old Rule for pH Dependence of Optical Rotation,” Journal of the American Chemical Society 130 (2008): 4404–4414.
J. T. Sorfleet and J. W. Shin, “Polarimetry Study of the Intrinsic Rotation of (1R,4R)‐(+)‐Camphor in Organic Solvents,” Chemical Physics 571 (2023): 111904.
D. P. Eyman and R. S. Drago, “Nuclear Magnetic Resonance Studies of Hydrogen Bonding,” Journal of the American Chemical Society 88 (1966): 1617–1620.
T. Matsuo, “Studies of the Solvent Effect on the Chemical Shifts in NMR Spectroscopy. II. Solutions of Succinic Anhydride, Maleic Anhydride, and the N‐Substituted Imides,” Canadian Journal of Chemistry 45 (1967): 1829–1835.
M. A. Weinberger and R. M. Heggie, “Solvent Effects in the Nuclear Magnetic Resonance Spectra of Benzalmalononitriles,” Canadian Journal of Chemistry 43 (1965): 2585–2593.
J. V. Hatton and R. E. Richards, “Solvent Effects in N.M.R. Spectra of Amide Solutions,” Molecular Physics 5 (1962): 139–152.
C. Djerassi, “Optical Rotatory Dispersion,” Endeavour 20 (1961): 138–145.
J. Zheng, K. Kwak, X. Chen, J. B. Asbury, and M. D. Fayer, “Formation and Dissociation of Intra−Intermolecular Hydrogen‐Bonded Solute−Solvent Complexes: Chemical Exchange Two‐Dimensional Infrared Vibrational Echo Spectroscopy,” Journal of the American Chemical Society 128 (2006): 2977–2987.
P. Dhanishta, P. S. S. Kumar, S. K. Mishra, and N. Suryaprakash, “Intramolecular Hydrogen Bond Directed Stable Conformations of Benzoyl Phenyl Oxalamides: Unambiguous Evidence From Extensive NMR Studies and DFT‐Based Computations,” RSC Advances 8 (2018): 11230–11240.
H. F. Ji, “A General Method to Predict Optical Rotations of Chiral Molecules From Their Structures,” RSC Advances 13 (2023): 4775–4780.