Application of the 2-deoxyglucose scaffold as a new chiral probe for elucidation of the absolute configuration of secondary alcohols
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Scientific Reports
ISSN: 2045-2322 - Publication year:
- 2022
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- Digital Object Identifier (open in new tab) https://doi.org/10.1038/s41598-022-21174-8
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- Dale, J. A, Mosher, H. S. Nuclear magnetic resonance enantiomer regents. configurational correlations via nuclear magnetic reso- nance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 1973, 95, 512-519. https:// doi. org/ 10. 1021/ ja007 83a034. open in new tab
- Ohtani, I., Kusumi, T., Ishitsuka, M. O., Kakisawa, H. Absolute configurations of marine diterpenes possessing a xenicane skeleton. An application of an advanced Mosher's method. Tetrahedron Lett. 1989, 30, 3147-3150. https:// doi. org/ 10. 1016/ S0040-4039(00) 99187-1. open in new tab
- Seco, J. M., Quiñoá, E. & Riguera, R. The assignment of absolute configuration by NMR. Chem. Rev. 104(1), 17-118. https:// doi. org/ 10. 1021/ cr000 665j (2004). open in new tab
- Kusumi, T., Fujita, Y., Ohtani, I. & Kakisawa, H. Anomaly in the modified Mosher's method: Absolute configurations of some marine cembranolides. Tetrahedron Lett. 32, 2923-2926. https:// doi. org/ 10. 1016/ 0040-4039(91) 80650-U (1991). open in new tab
- Ohtani, I., Kusumi, T., Kashman, Y., Kakisawa, H. A new aspect of the high-field NMR application of Mosher's method. The absolute configuration of marine triterpene sipholenol A. J. Org. Chem. 1991, 56, 1296-1298. https:// doi. org/ 10. 1021/ jo000 03a067. open in new tab
- Ichikawa, A., Hiradate, S., Sugio, A., Kuwahara, S., Watanabe, M., Harada, N. Absolute configuration of 2-methoxy-2-(2-naphthyl) propionic acid as determined by the 1 H NMR anisotropy method. Tetrahedron: Asymmetry 2000, 11, 2669-2675. https:// doi. org/ 10. 1016/ S0957-4166(00) 00233-0. open in new tab
- Cimmino, A., Masi, M., Evidente, M., Superchi, S. & Evidente, A. Application of Mosher's method for absolute configuration assignment to bioactive plants and fungi metabolites. J. Pharm. Biomed. Anal. 144, 59-89. https:// doi. org/ 10. 1016/J. JPBA. 2017. 02. 037 (2017). open in new tab
- Joshi, B. S., Newton, M. G., Lee, D. W., Barber, A. D. & Pelletier, S. W. Reversal of absolute stereochemistry of the pyrrolo[2,1-b] quinazoline alkaloids vasicine, vasicinone, vasicinol and vasicinolone. Tetrahedron Asymmetry 7, 25-28. https:// doi. org/ 10. 1016/ 0957-4166(95) 00412-2 (1996). open in new tab
- Ohtani, I., Kusumi, T., Kashman, Y., Kakisawa, H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 1991, 113, 4092-4096. https:// doi. org/ 10. 1021/ ja000 11a006. open in new tab
- Karkare, S. et al. Cytotoxic cardenolide glycosides of roupellina (Strophanthus) Boivinii from the Madagascar Rainforest. J. Nat. Prod. 70, 1766-1770. https:// doi. org/ 10. 1021/ np070 336n (2007). open in new tab
- Lundborg, M., Fontana, C. & Widmalm, G. Automatic structure determination of regular polysaccharides based solely on NMR spectroscopy. Biomacromol 12, 3851-3855. https:// doi. org/ 10. 1021/ bm201 169y (2011). open in new tab
- Wenzel, T. J. Differentiation of Chiral Compounds Using NMR Spectroscopy; open in new tab
- Yang, S., Bian, G., Sa, R., Song, L. Assigning the absolute configurations of chiral primary amines based on experimental and DFT-calculated 19F nuclear magnetic resonance. Front. Chem. 2019. https:// doi. org/ 10. 3389/ fchem. 2019. 00318. open in new tab
- Khatri Chhetri, B. et al. Peyssonnosides A-B, unusual diterpene glycosides with a sterically encumbered cyclopropane motif: structure elucidation using an integrated spectroscopic and computational workflow. J. Org. Chem. 84, 8531-8541. https:// doi. org/ 10. 1021/ acs. joc. 9b008 84 (2019). open in new tab
- Seroka, P., Płosiński, M., Czub, J., Sowiński, P. & Pawlak, J. Monosaccharides as internal probes for the determination of the absolute configuration of 2-BUTANOL. Magn. Reson. Chem. 44, 132-138. https:// doi. org/ 10. 1002/ mrc. 1735 (2006). open in new tab
- Laskowski, T. et al. Monosaccharides as potential chiral probes for the determination of the absolute configuration of secondary alcohols. J. Nat. Prod. 79, 2797-2804. https:// doi. org/ 10. 1021/ acs. jnatp rod. 6b004 71 (2016). open in new tab
- Bennett, C. S. & Galan, M. C. Methods for 2-deoxyglycoside synthesis. Chem. Rev. 118, 7931-7985. https:// doi. org/ 10. 1021/ acs. chemr ev. 7b007 31 (2018). open in new tab
- Hou, D. & Lowary, T. L. Recent advances in the synthesis of 2-deoxy-glycosides. Carbohydr. Res. 344(15), 1911-1940. https:// doi. org/ 10. 1016/j. carres. 2009. 07. 013 (2009). open in new tab
- Tvaroska, I., Taravel, F. R. Carbon-proton coupling constants in the conformational analysis of sugar molecules. In Advances in Carbohydrate Chemistry and Biochemistry; open in new tab
- Horton, D., Ed.; Academic Press, 1995, 51, 15-61. https:// doi. org/ 10. 1016/ S0065- 2318(08) 60191-2. open in new tab
- Aytenfisu, A. H., Yang, M. & Mackerell, A. D. CHARMM drude polarizable force field for glycosidic linkages involving pyranoses and furanoses. J. Chem. Theory Comput. 14, 3132-3143. https:// doi. org/ 10. 1021/ acs. jctc. 8b001 75 (2018). open in new tab
- Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Had, M. & F, D. J. Gaussian 09, Revision D.01. Gaussian Inc., Wallingford 2013.
- Vanommeslaeghe, K. et al. CHARMM General Force Field: a force field for drug-like molecules compatible with the CHARMM all-atom additive biological force fields. J. Comput. Chem. 31, 671-690. https:// doi. org/ 10. 1002/ jcc. 21367 (2010). open in new tab
- Abraham, M. J. et al. GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX 1-2, 19-25. https:// doi. org/ 10. 1016/J. SOFTX. 2015. 06. 001 (2015). open in new tab
- R Core Team R: A Language and Environment for Statistical Computing 2020. open in new tab
- Oroshnik, W., Mebane, A. D. The Polyene Antifungal Antibiotics. In Progress in the Chemistry of Organic Natural Products/ Progrès Dans La Chimie Des Substances Organiques Naturelles; open in new tab
- Bangert, R., Bonner, J., Brockmann, H., Crombie, L., Jaenicke, L., Kutzbach, C., Mebane, A. D., Muxfeldt, H., Oroshnik, W., Zechmeister, L., Eds.; Fortschritte Der Chemie Organischer Naturstoffe; open in new tab
- Springer: Vienna, 1963; pp 17-79. https:// doi. org/ 10. 1007/ 978-3-7091-7149-3_2. open in new tab
- Hamilton-Miller, J. Chemistry and biology of the polyene macrolid antibiotics. Bacteriol. Rev. 37, 166-196. https:// doi. org/ 10. 1128/ MMBR. 37.2. 166-196. 1973 (1973). open in new tab
- Szwarc, K., Szczeblewski, P., Sowiński, P., Borowski, E. & Pawlak, J. The structure, including stereochemistry, of levorin A1. Magn. Reson. Chem. 53(6), 479-484. https:// doi. org/ 10. 1002/ mrc. 4229 (2015). open in new tab
- Szczeblewski, P., Laskowski, T., Kubacki, B., Dziergowska, M., Liczmańska, M., Grynda, J., Kubica, P., Kot-Wasik, A., Borowski, E. Analytical studies on ascosin, candicidin and levorin multicomponent antifungal antibiotic complexes. The stereostructure of ascosin A2. Sci. Rep. 2017 7(1), 40158. https:// doi. org/ 10. 1038/ srep4 0158. open in new tab
- Borzyszkowska-Bukowska, J., Szczeblewski, P., Konkol, A., Grynda, J., Szwarc-Karabyka, K. & Laskowski, T. The complete stereo- chemistry of the antibiotic candicidin A3 (syn. ascosin A3, levorin A3). Nat. Prod. Res. 2019, 34, 2869-2879. https:// doi. org/ 10. 1080/ 14786 419. 2019. 15960 95. open in new tab
- Szczeblewski, P. et al. Ipertrofan revisited-The proposal of the complete stereochemistry of mepartricin A and B. Molecules 26(5533), 5533. https:// doi. org/ 10. 3390/ molec ules2 61855 33 (2021). open in new tab
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