A Novel NADH Model: Design, Synthesis, and its Chiral Reduction and Fluorescent Emission
A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with C 3 symmetry was designed and synthesized. Hydrogens at the C‐4 position of all dihydropyridine rings in the inner part of the bowl could transfer to the substrate with powerful enantioselectivity. This novel C 3 symmetrical...
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| Published in | Advanced synthesis & catalysis Vol. 351; no. 18; pp. 3045 - 3050 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.12.2009
Wiley |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with
C
3
symmetry was designed and synthesized. Hydrogens at the C‐4 position of all dihydropyridine rings in the inner part of the bowl could transfer to the substrate with powerful enantioselectivity. This novel
C
3
symmetrical NADH model is capable of fluorescence emission at 455 nm when excited at 390 nm. |
|---|---|
| AbstractList | A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with
C
3
symmetry was designed and synthesized. Hydrogens at the C‐4 position of all dihydropyridine rings in the inner part of the bowl could transfer to the substrate with powerful enantioselectivity. This novel
C
3
symmetrical NADH model is capable of fluorescence emission at 455 nm when excited at 390 nm. A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with C-3 symmetry was designed and synthesized. Hydrogens at the C-4 position of all dihydropyridine rings in the inner part of the bowl could transfer to the substrate with powerful enantioselectivity. This novel C-3 symmetrical NADH model is capable of fluorescence emission at 455 nm when excited at 390 nm. A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with C3 symmetry was designed and synthesized. Hydrogens at the C-4 position of all dihydropyridine rings in the inner part of the bowl could transfer to the substrate with powerful enantioselectivity. This novel C3 symmetrical NADH model is capable of fluorescence emission at 455 nm when excited at 390 nm. |
| Author | Zhao, Jia Wang, Nai-Xing |
| Author_xml | – sequence: 1 givenname: Nai-Xing surname: Wang fullname: Wang, Nai-Xing email: nxwang@mail.ipc.ac.cn organization: Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China – sequence: 2 givenname: Jia surname: Zhao fullname: Zhao, Jia organization: Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China |
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| CitedBy_id | crossref_primary_10_1021_acs_orglett_5b03700 crossref_primary_10_1039_C5RA20977C crossref_primary_10_1039_c3cs35466k crossref_primary_10_2174_1570178618666210706112141 crossref_primary_10_1002_chem_201000244 crossref_primary_10_1039_C5CP03114A crossref_primary_10_1021_acsomega_8b01815 crossref_primary_10_1038_srep17458 crossref_primary_10_1002_chem_201402763 crossref_primary_10_1080_00397911_2010_505702 crossref_primary_10_2174_1570178619666220127122333 crossref_primary_10_1021_ol502486f crossref_primary_10_1038_srep20163 crossref_primary_10_1016_j_tetlet_2014_02_095 crossref_primary_10_1039_D0CC05185C crossref_primary_10_1039_c1cs15268h |
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| Keywords | enantioselectivity synthesis magnesium(II) ASYMMETRIC TRANSFER HYDROGENATION chiral NADH model BENZOYLFORMATE MIMICS STEREOSELECTIVE REDUCTION AUXILIARY HYDRIDE TRANSFER LIGANDS fluorescence 1,4-DIHYDROPYRIDINES ESTERS CHEMISTRY |
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| References_xml | – reference: K. J. Wallace, W. J. Belcher, D. R. Turner, K. F. Syed, W. J. Steed, J. Am. Chem. Soc. 2003, 125, 9699-9715. – reference: W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3070; – reference: U. Eisner, J. Kuthan, Chem. Rev. 1972, 72, 1-42; – reference: Y. Murakami, J.-i. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721-758; – reference: P. Jouin, C. B. Troostwijk, R. M. Kellogg, J. Am. Chem. Soc. 1981, 103, 2091-2093; – reference: K. Skog, O. Wennerström, Tetrahedron Lett. 1992, 33, 1751-1754; – reference: K. Skog, O. Wennerström, Tetrahedron Lett. 1995, 36, 4629-4632; – reference: M. Seki, N. Baba, J. Oda, Y. Inouye, J. Am. Chem. Soc. 1981, 103, 4613-4615; – reference: S. L. You, Chem. Asian J. 2007, 2, 820-827. – reference: V. Sashuk, D. Schoeps, H. Plenio, Chem. Commun. 2009, 770-772. – reference: W. P. Cochrane, P. L. Pauson, T. S. Stevens, J. Chem. Soc. C 1968, 630-632; – reference: Y. Combret, J. Duflos, G. Dupas, J. Bourguignon, G. 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| Snippet | A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with
C
3
symmetry was designed and synthesized. Hydrogens at the C‐4 position of all... A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with C-3 symmetry was designed and synthesized. Hydrogens at the C-4 position of all... A novel chiral nicotinamide adenine dinucleotide hydrogen (NADH) model with C3 symmetry was designed and synthesized. Hydrogens at the C-4 position of all... |
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| SubjectTerms | Chemistry Chemistry, Applied Chemistry, Organic chiral NADH model enantioselectivity fluorescence magnesium(II) Physical Sciences Science & Technology synthesis |
| Title | A Novel NADH Model: Design, Synthesis, and its Chiral Reduction and Fluorescent Emission |
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