Design and synthesis of new classes of heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by Asymmetric Multicomponent Reactions (AMCRs)

Accounts of Chemical Research

Volumn 39, Issue 7, 2006, Pages 451-463

  Dondoni, Alessandro ^a   Massi, Alessandro ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOHYDRATE; CARBON; GLYCOCONJUGATE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; GLYCOSYLATION; SYNTHESIS;

AMINO ACIDS; CARBOHYDRATES; CARBON; GLYCOCONJUGATES; GLYCOSYLATION; HETEROCYCLIC COMPOUNDS;

EID: 33746897660     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar068023r     Document Type: Article

References (45)

1. Breinbauer, R.; Vetter, I. R.; Waldmann, H. From protein domains to drug candidates-natural products as guiding principles in the design and synthesis of compound libraries. Angew. Chem., Int. Ed. 2002, 41, 2878-2890.
2. Perspectives in Nucleosides and Nucleic Acid Chemistry; Kisakürek, M. V., Rosemeyer, H., Eds.; Wiley-VCH: Weinheim, Germany, 2001.
3. Izawa, K. Synthesis of unnatural amino acids and application to pharmaceuticals. Farumashia 2005, 41, 319-323.
4. For several articles concerning β-lactam synthesis and biological activity, see the thematic issue of Tetrahedron 2000, 56, 5553-5742.
5. Multicomponent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
6. Andraos, J. Unification of reaction metrics for green chemistry II: Evaluation of named organic reactions and application to reaction discovery. Org. Process Res. Dev. 2005, 9, 149-163.
7. Adams, D. J.; Dyson, P. J.; Tavenerg, S. T. Chemistry In Alternative Reaction Media; John Wiley & Son, Ltd: Chichester, U.K., 2004.
8. Asymmetric Organocatalysis; Berkessel, A., Gröger, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
9. Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, Germany, 2005.
10. Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis; Wipf, P., Ed.; John Wiley & Son, Ltd: Chichester, U.K., 2005 and references therein.
11. Yoshida, J.; Itami, K. Tag Strategy for Separation and Recovery. Chem. Rev. 2002, 102, 3693-3716.
12. Jas, G.; Kirschning, A. Continuous Flow Techniques in Organic Synthesis. Chem. - Eur. J. 2003, 9, 5708-5723.
13. Ramón, D. J.; Yus, M. Asymmetric Multicomponent Reactions (AMCRs): The New Frontier. Angew. Chem., Int. Ed. 2005, 44, 1602-1634.
14. List, B. Enamine Catalysis Is a Powerful Strategy for the Catalytic Generation and Use of Carbanion Equivalents. Acc. Chem. Res. 2004, 37, 548-557.
15. Lockhoff, O. An Access to Glycoconjugate Libraries through Multicomponent Reactions. Angew. Chem., Int. Ed. 1998, 37, 3436-3439.
16. Postema, M. H. D.; Calimente, D. In Glycochemistry: Principles, Synthesis and Applications; Wang, P. G., Bertozzi, C., Eds.; Marcel Dekker: New York, 2000; Chapter 4, pp 77-131.
17. For a typical and recent case, see the effect of glycosylation in guanidines: Lin, P.; Lee, C. L.; Sim, M. M. Synthesis of Novel Guanidinoglycoside: 2-Glycosylamino 4,5-Dihydro-6-Pyrimidinone. J. Org. Chem. 2001, 66, 8243-8247.
18. For a review, see: Kappe, C. O. Recent Advances in the Biginelli Dihydropyrimidine Synthesis. New Tricks from an Old Dog. Acc. Chem. Res. 2000, 33, 879-888.
19. For a review, see: Lavilla, R. Recent Developments in the Chemistry of Dihydropyridines. J. Chem. Soc., Perkin Trans. 1 2002, 9, 1141-1156.
20. Wu, Q.; Simons, C. Synthetic Methodologies for C-Nucleosides. Synthesis 2004, 10, 1533-1553 and references therein.
21. Dondoni, A. Formylation of Carbohydrates and the Evolution of Synthetic Routes to Artificial Oligosaccharides and Glycoconjugates. Pure Appl. Chem. 2000, 72, 1577-1588.
22. Dondoni, A.; Massi, A.; Sabbatini, S.; Bertolasi, V. Three-component Biginelli Cyclocondensation Reaction Using C-glycosylated Substrates. Preparation of a Collection of Dihydropyrimidinone Glycoconjugates and the Synthesis of C-glycosylated Monastrol Analogues. J. Org. Chem. 2002, 67, 6979-6994.
23. Dondoni, A.; Massi, A.; Minghini, E.; Bertolasi, V. Dihydropyridine C-Glycoconjugates by Hantzsch Cyclocondensation. Synthesis of a C(6)-Glycosylated Nifedipine Analogue. Helv. Chim. Acta 2002, 35, 3331-3348.
24. Dondoni, A.; Massi, A. Decoration of Dihydropyrimidine and Dihydropyridine Scaffolds with Sugars via Biginelli and Hantzsch Multicomponent Reactions: An Efficient Entry to a Collection of Artificial Nucleosides. Mol. Diversity 2003, 6, 261-270.
25. Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Small Molecule Inhibitor of Mitotic Spindle Bipolarity Identified in a Phenotype-Based Screen. Science 1999, 286, 971-974.
26. Marcus, A. I.; Peters, U.; Thomas, S. L.; Garrett, S.; Zelnak, A.; Kapoor, T. M.; Giannakakou, P. Mitotic Kinesin Inhibitors Induce Mitotic Arrest and Cell Death in Taxol-resistant and-sensitive Cancer Cells. J. Biol. Chem. 2005, 280, 11569-11577.
27. Experiments performed in the laboratory of Prof. F. Kozielski in Grenoble, France. We thank Prof. F. Kozielski for the permission to report here these results.
28. Dondoni, A.; Marra, A.; Zampolli, M. G. Synthesis of All Carbon Linked Glycoside Clusters Round Benzene Scaffold via Sonogashira-Heck-Cassar Cross-Coupling of Iodobenzenes with Ethynyl C-Glycosides. Synlett 2002, 11, 1850-1854.
29. Lundquist, J. J.; Toone, E. J. The Cluster Effect. Chem. Rev. 2002, 102, 555-578.
30. Bertozzi, C. R.; Kiessling, L. L. Chemical Glycobiology. Science 2001, 291, 2357-2364.
31. Dondoni, A.; Marra, A. Methods for Anomeric Carbon-Linked and Fused Sugar Amino Acid Synthesis: The Gateway to Artificial Glycopeptides. Chem. Rev. 2000, 100, 4395-4421 and references therein.
32. Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. β-Peptides: From Structure to Function. Chem. Rev. 2001, 101, 3219-3232.
33. McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Development of Co- and Post-translational Synthetic Strategies to C-Neoglycopeptides. Org. Lett. 2002, 4, 3591-3594.
34. Palomo, C.; Oiarbide, M.; Landa, A.; González-Rego, M. C.; García, J. M.; González, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. Design and Synthesis of a Novel Class of Sugar-Peptide Hybrids: C-Linked Glyco β-Amino Acids through a Stereoselective "Acetate" Mannich Reaction as the Key Strategic Element. J. Am. Chem. Soc. 2002, 124, 8637-8643.
35. Dondoni, A.; Massi, A.; Sabbatini, S. Multiple Component Approaches to C-Glycosyl β-Amino Acids by Complementary One-pot Mannich-Type and Reformatsky-Type Reactions. Chem. - Eur. J. 2005, 11, 7110-7125.
36. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V. A., Ed.; Wiley & Son, Ltd: Chichester, U.K., 1999.
37. Guignard, B.; Entenza, J. M.; Moreillon, P. β-Lactams against Methicillin-Resistant Staphylococcus aureus. Curr. Opin. Pharmacol. 2005, 5, 479-489.
38. Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide M. Asymmetric Synthesis of β-Lactams by Staudinger Ketene-Imine Cycloaddition Reaction. Eur. J. Org. Chem. 1954, 19, 3223-3235.
39. Dondoni, A.; Massi, A.; Sabbatini, S.; Bertolasi, V. Three-Component Staudinger-Type Stereoselective Synthesis of C-Glycosyl-β-Lactams and their Use as Precursors for C-Glycosyl Isoserines and Dipeptides. A Polymer-Assisted Solution-Phase Approach. Adv. Synth. Catal. 2004, 346, 1355-1360.
40. Peptides 2000: Proceedings of the Twenty-Sixth European Peptide Symposium; Martinez, J., Fehrentz, J. A., Eds.; EDK: Paris, 2001.
41. Kuwahara, M.; Arimitsu, M.; Sisido, M. Synthesis of δ-Amino Acids with an Ether Linkage in the Main Chain and Nucleobases on the Side Chain as Monomer Units for Oxy-Peptide Nucleic Acids. Tetrahedron 1999, 55, 10067-10078 and references therein.
42. Rosenthal, G. A. Plant Nonprotein Amino and Imino Acids. Biological, Biochemical, and Toxicological Properties; Academic Press: New York, 1982.
43. Garner, P.; Yoo, J. U.; Sarubu, R.; Kennedy, V. O.; Youngs, W. J. Stereocontrolled and Enantioselective Synthesis of the Branched 6-Amino-4,6-Deoxyheptopyranuronic Acid Component of Amipurimycin. Tetrahedron 1998, 54, 9303-9316.
44. Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. Model Studies Toward the Synthesis of Dihydropyrimidinyl and Pyridyl α-Amino Acids via Three-Component Biginelli and Hantzsch Cyclocondensations. J. Org. Chem. 2003, 68, 6172-6183.
45. Dondoni, A.; Massi, A.; Minghini, E.; Bertolasi, V. Multicomponent Hantzsch Cyclocondensation as a Route to Highly Functionalized 2- and 4-Dihydropyridylalanines, 2- and 4-Pyridylalanines, and Their N-oxides: Preparation via a Polymer-Assisted Solution-Phase Approach. Tetrahedron 2004, 60, 2311-2326.