I2-catalyzed oxidative condensation of aldoses with diamines: Synthesis of aldo-naphthimidazoles for carbohydrate analysis

Molecules

Volumn 15, Issue 3, 2010, Pages 1340-1353

  Lin, Chunchi ^a   Hung, Wei Ting ^a   Kuo, Chien Yuan ^a   Liao, Kuo Shiang ^a   Liu, Yin Chen ^a   Yang, Wen Bin ^a  

^a GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

Aldo imidazole (aldo IM); Iodine; Matrix assisted laser desorption ionization time of flight mass spectrometry (MALDI TOF MS); Saccharides

Indexed keywords

CARBOHYDRATE; IODINE; NAPHTHALIMIDE DERIVATIVE;

ARTICLE; CAPILLARY ELECTROPHORESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION;

CARBOHYDRATES; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROPHORESIS, CAPILLARY; IODINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NAPHTHALIMIDES; OXIDATION-REDUCTION; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 77950358068     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15031340     Document Type: Article

References (24)

1. More, S. V.; Sastry, M. N. V.; Wang, C. C.; Yao, C. F. Molecular iodine: A powerful catalyst for the easy and efficient synthesis of quinoxalines. Tetrahedron Lett. 2005, 46, 6345-6348.
2. Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C. F. Molecular iodine-catalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction. Tetrahedron Lett. 2005, 46, 7183-7186.
3. Wu, J.; Xia, H. G.; Gau, K. Molecular iodine: A highly efficient catalyst in the synthesis of quinolines via Friedländer annulation. Org. Biomol. Chem. 2006, 4, 126-129.
4. Pasha, M. A.; Jayashankara, V. P. Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a, j]xanthenes under solvent-free condition. Bioorg. Med. Chem. Lett. 2007, 17, 621-623.
5. Lin, X. F.; Cui, S. L.; Wang, Y. G. Molecular iodine-catalyzed one-pot synthesis of substituted quinolines from imines and aldehydes. Tetrahedron Lett. 2006, 47, 3127-3130.
6. Yadav, J. S.; Subba Reddy, B. V.; Narayana Kumar, G. G. K. S.; Swamy, T. Iodine as a versatile reagent for the Prins-cyclization: an expeditious synthesis of 4-iodotetrahydropyran derivatives. Tetrahedron Lett. 2007, 48, 2205-2208. (Pubitemid 46275846)
7. Kidwai, M.; Mothsra, P. A one-pot synthesis of 1, 2,4,5- tetraarylimidazoles using molecular iodine as an efficient catalyst. Tetrahedron Lett. 2006, 47, 5029-5031. (Pubitemid 43867632)
8. Gogoi, P.; Konwar, D. An efficient and one-pot synthesis of imidazolines and benzimidazoles via anaerobic oxidation of carbon-nitrogen bonds in water. Tetrahedron Lett. 2006, 47, 79-82. (Pubitemid 41743780)
9. Lin, C.; Lai, P. T.; Liao, K. S.; Hung, W. T.; Yang, W. B.; Fang, J. M. Using molecular iodine in direct oxidative condensation of aldoses with diamines: An improved synthesis of aldobenzimidazoles and aldo-naphthimidazoles for carbohydrate analysis. J. Org. Chem. 2008, 73, 3848-3853.
10. Koch, K. E. Carbohydrate-modulated gene expression in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1996, 47, 509-540. (Pubitemid 126669764)
11. Larsen, K.; Thygesen, M. B.; Guillaumie, F.; Willats, W. G. T.; Jensen, K. J. Solid-phase chemical tools for glycobiology. Carbohydr. Res. 2006, 341, 1209-1234. (Pubitemid 43795413)
12. Togo, H.; Iida, S. Synthetic use of molecular iodine for organic synthesis. Synlett 2006, 2159-2175. (Pubitemid 44393514)
13. Colombeau, L.; Traoré, T.; Compain, P.; Martin, O. R. Metal-free one-pot oxidative amidation of aldoses with functionalized amines. J. Org. Chem. 2008, 73, 8647-8650.
14. Ishihara, M.; Togo, H. An efficient preparation of 2-imidazolines and imidazoles from aldehydes with molecular iodine and (diacetoxyiodo) benzene. Synlett 2006, 227-230. (Pubitemid 43221303)
15. Ishihara, M.; Togo, H. Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine. Tetrahedron 2007, 63, 1474-1480. (Pubitemid 47031238)
16. Anumula, K. R. Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. Anal. Biochem. 2006, 350, 1-23.
17. Hillenkamp, F.; Jasna, P. K. MALDI MS: A Practical Guide to Instrumentation, Methods and Applications; Wiley-VCH: Weinheim, Germany, 2007.
18. Deisewerd, K. The desorption process in MALDI. Chem. Rev. 2003, 103, 395-425.
19. Harvey, D. J. Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update covering the period 2001-2002. Mass Spectrom. Rev. 2008, 27, 125-201.
20. Ojima, N.; Masuda, K. J.; Tanaks, K.; Nishimura, O. Analysis of neutral oligosaccharides for structural characterization by matrix-assisted laser desorption/ionization quadrupole ion trap time-of-flight mass spectrometry. J. Mass Spectrom. 2005, 40, 380-388.
21. Hsu, N. Y.; Yang, W. B.; Wong, C. H.; Lee, Y. C.; Lee, R. T.; Wang, Y. S.; Chen, C. H. Matrix-assisted laser desorption-ionization mass spectrometry of polysaccharides with 2',4',6'-trihydroxyacetophenone as matrix. Rapid Commun. Mass Spectrom. 2007, 21, 2137-2146.
22. Hung, W. T.; Wang, S. H.; Chen, C. H.; Yang, W. B. Structure determination of β-glucans from Ganoderma lucidum with matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. Molecules 2008, 13, 1538-1550.
23. Snovida, S. I.; Perreault, H. A 2,5-dihydroxybenzoic acid/N, N-dimethylaniline matrix for the analysis of oligosaccharides by matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 3711-3715.
24. Lin, C.; Hung, W. T.; Chen, C. H.; Fang, J. M.; Yang, W. B. A new naphthimidazole derivative for saccharide labeling with enhanced sensitivity in mass spectrometry detection. Rapid Commun. Mass Spectrom. 2010, 24, 85-94.