Recent advances in monosaccharide synthesis: A journey into L-hexose world

Current Organic Chemistry

Volumn 13, Issue 1, 2009, Pages 71-98

  D'Alonzo, Daniele ^a   Guaragna, Annalisa ^a   Palumbo, Giovanni ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSE; KETONES;

BIOACTIVE COMPOUNDS; CARBON CHAINS; CHAIN ELONGATION; GENERAL METHODOLOGIES; GLYCOMICS; GLYCOPEPTIDES; HIGH PURITY; L-ENANTIOMERS; PRESSUNG; SYNTHETIC ROUTES;

OLIGOSACCHARIDES;

EID: 65249156033     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527209787193828     Document Type: Review

References (170)

1. Shriver, Z.; Raguram, S.; Sasisekharan, R. Nat. Rev. Drug Discov., 2004, 3, 863.
2. Dwek, R.A. Chem. Rev., 1996, 96, 683.
3. Gabius, H.-J.; Gabius, S. Glycosciences, Chapman & Hall: London, 1997.
4. Liu, D.; Shriver, Z.; Venkataraman, G.; El Shabrawi, Y.; Sasisekharan, R. Proc. Natl. Acad. Sci. USA, 2002, 99, 568.
5. Dube, D.H.; Bertozzi, C.R. Nat. Rev. Drug Discov., 2005, 4, 477.
6. Shriver, Z.; Liu, D.; Sasisekharan, R. Trends Cardiovasc. Med., 2002, 12, 71.
7. Rudd, P.M.; Elliott, T.; Cresswell, P.; Wilson, I.A.; Dwek, R.A. Science, 2001, 291, 2370.
8. Fu, X.; Albermann, C.; Jiang, J.; Liao, J.; Zhang, C.; Thorson, J.S. Nat. Biotechnol., 2003, 21, 1467.
9. McNaught, A.D. Pure Appl. Chem., 1996, 68, 1919.
10. (a) Collins, P.M. Dictionary of Carbohydrates, Chapman and Hall: London, 1987.
11. (b) Lee, J.-C.; Chang, S.-W.; Liao, C.-C.; Chi, F.-C.; Chen, C.-S.; Wen, Y.-S.; Wang, C.-C.; Kulkarni, S.S.; Puranik, R.; Liu, Y.-H.; Hung, S.-C. Chem. Eur. J., 2004, 10, 399.
12. (a) Lindahl, U. Pure Appl. Chem., 1997, 69, 1897.
13. (b) Iozzo, R.V. Annu. Rev. Biochem., 1998, 67, 609.
14. (c) Rabenstein, D.L. Nat. Prod. Rep., 2002, 19, 312.
15. Burger, R.M. Chem. Rev., 1998, 98, 1153 and references therein cited.
16. Ogita, T.; Otake, N.; Miyazaki, Y.; Yonehara, H.; Macfarlane, R.D.; McNeal, C.J. Tetrahedron Lett., 1980, 21, 3203.
17. Stack, R.J. FEMS Microbiol. Lett., 1987, 48, 83.
18. Li, Y.-S.; Matsunaga, K.; Ishibashi, M.; Ohizumi, Y. J. Org. Chem., 2001, 66, 2165.
19. (a) Kubelka, W.; Kopp, B.; Jentsch, K. Phytochemistry, 1974, 13, 1805.
20. (b) Esaki, S.; Ohishi, A.; Katsumata, A.; Sugiyama, N.; Kamiya, S. Biosci. Biotechnol. Biochem., 1993, 57, 2099.
21. Hudlicky, T.; Entwistle, D.A.; Pitzer, K.K.; Thorpe, A.J. Chem. Rev., 1996, 96, 1195.
22. (a) Nicolaou, K.C.; Sorensen, E.J. Classics in Total Synthesis, VCH: Weinheim, 1996.
23. (b) Schmidt, R.R. Pure Appl. Chem., 1987, 59, 415.
24. Fraser-Reid, B.; Tatsuta, K.; Thiem, J. Glycoscience: Chemistry and Chemical Biology, Springer: Berlin, 2001.
25. Dondoni, A.; Marra, A. Chem. Rev., 2004, 104, 2557 and references therein cited.
26. (a) Vogel, P. Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B.; Tatsuta, K.; Thiem, J. Eds.; Springer: Berlin, 2001; pp. 1023.
27. (b) Vogel, P. The organic chemistry of sugars; Levy, D.E.; Fugedi, P. Eds.; CRC Press/Taylor & Francis: Boca Raton, 2006, Vol. II, pp. 629.
28. Lin, G.-Q.; Li, Y.-M.; Chan, A.S.C. Principles and Applications of Asymmetric Synthesis, John Wiley & Sons, Inc.: New York, 2001.
29. (a) This route has been independently developed by two different research groups: (a) Kim, K.S.; Cho, B.H.; Shin, I. Bull. Korean Chem. Soc., 2002, 23, 1193.
30. (b) Ermolenko, L.; Sasaki, N.A.; Potier, P. Helv. Chim. Acta, 2003, 86, 3578.
31. (c) Ermolenko, L.; Sasaki, N.A. J. Org. Chem., 2006, 71, 693.
32. Abushanab, E.; Vemishetti, P.; Leiby, R.W.; Singh, H.K.; Mikkilineni, A.B.; Wu, D.C.-J.; Saibaba, R.; Panzica, R.P. J. Org. Chem., 1988, 53, 2598.
33. Saïah, M.; Bessodes, M.; Antonakis, K. Tetrahedron Lett., 1992, 33, 4317.
34. Usual Kishi's procedure for olefin dihydroxylation resulted in a low syn/anti selectivity, see: Cha, J.K.; Christ, W.J.; Kishi, Y. Tetrahedron, 1984, 40, 2247.
35. (a) Horeau, A.; Kagan, H.B.; Vigneron, J.P. Bull. Soc. Chim. Fr., 1968, 9, 3795.
36. (b) Masamune, S.; Choy, W.; Petersen, J.S.; Sita, L.R. Angew. Chem. Int. Ed., 1985, 24, 1.
37. Metz, P. Topics in Current Chemistry, Springer-Verlag: Berlin Heidelberg, 2001.
38. (a) Corey, E.J.; Seebach, D. Angew. Chem., Int. Ed., 1965, 4, 1075.
39. (b) Corey, E.J.; Seebach, D. Angew. Chem., Int. Ed., 1965, 4, 1077.
40. (a) Yus, M.; Najera, C.; Foubelo, F. Tetrahedron, 2003, 59, 6147.
41. (b) Degl'Innocenti, A.; Pollicino, S.; Capperucci, A. Chem. Commun., 2006, 4881.
42. (c) Kirschning, A.; Kujat, C.; Luiken, S.; Schaumann, E. Eur. J. Org. Chem., 2007, 2387.
43. Enders, D.; Vázquez, J.; Raabe, G. Eur. J. Org. Chem., 2000, 893.
44. Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Chem. Soc. Rev., 2000, 29, 109.
45. Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. J. Org. Chem., 1997, 62, 9369.
46. Guaragna, A.; Palumbo, G.; Pedatella, S. e-Encyclopedia of Reagents for Organic Synthesis; Paquette, L.A. Ed.; John Wiley & Sons: New York, 2008.
47. Caputo, R.; Festa, P.; Guaragna, A.; Palumbo, G.; Pedatella, S. Carbohydr. Res., 2003, 338, 1877.
48. Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S.; Solla, F. Eur. J. Org. Chem., 2002, 534.
49. Guaragna, A.; D'Errico, S.; D'Alonzo, D.; Pedatella, S.; Palumbo, G. Org. Lett., 2007, 9, 3473.
50. (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S.; Solla, F. J. Carbohydr. Chem., 2000, 19, 631.
51. (b) Caputo, R.; De Nisco, M.; Festa, P.; Guaragna, A.; Palumbo, G.; Pedatella, S. J. Org. Chem., 2004, 69, 7033.
52. (a) Caputo, R.; Guaragna, A.; Palumbo, G.; Pedatella, S. Nucleosides Nucleotides, 1999, 18, 651.
53. (b) Guaragna, A.; D'Alonzo, D.; De Nisco, M.; Pedatella, S.; Palumbo, G. Nucleosides Nucleotides Nucleic Acids, 2007, 26, 959.
54. (c) D'Alonzo, D.; Guaragna, A.; Van Aerschot, A.; Herdewijn, P.; Palumbo, G. Tetrahedron Lett., 2008, 49, 6068.
55. (a) Guaragna, A.; Napolitano, C.; D'Alonzo, D.; Pedatella, S.; Palumbo, G. Org. Lett., 2006, 8, 4863.
56. (b) D'Alonzo, D.; Guaragna, A.; Napolitano, C.; Palumbo, G. J. Org. Chem., 2008, 73, 5636.
57. For a review on the synthetic utility of isopropylidene-D- and L-glyceraldehyde, see: Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron, 1986, 42, 447.
58. (a) Becker, S.; Fort, Y.; Caubère, P. J. Org. Chem., 1990, 55, 6194.
59. (b) Caputo, R.; Palumbo, G.; Pedatella, S. Tetrahedron, 1994, 50, 7265.
60. (a) Bols, M. Carbohydrate building blocks, Wiley: New York, 1996.
61. (b) Kulkarni, S.S.; Lee, J.-C.; Hung, S.-C. Curr. Org. Chem., 2004, 8, 475.
62. Honzumi, M.; Taniguchi, T.; Ogasawara, K. Org. Lett., 2001, 3, 1355.
63. For further synthetic applications of this building block, see for example: Honzumi, M.; Ogasawara, K. Tetrahedron Lett., 2002, 43, 1047.
64. (a) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. Synthesis, 1993, 948.
65. (b) Konno, H.; Ogasawara, K. Synthesis, 1999, 1135.
66. Hiroya, K.; Kurihara, Y.; Ogasawara, K. Angew. Chem. Int. Ed., 1995, 34, 2287.
67. Ogasawara, K. J. Synth. Org. Chem. Jpn., 1999, 57, 957.
68. Taylor, M.S.; Jacobsen, E.N. Proc. Natl. Acad. Sci. USA, 2004, 101, 5368.
69. Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B. Chem. Rev., 1994, 94, 2483.
70. Ahmed, Md.M.; O'Doherty, G.A. Tetrahedron Lett., 2005, 46, 3015.
71. Hunter, T.J.; O'Doherty, G.A. Org. Lett., 2001, 3, 1049.
72. Ahmed, Md.M.; Berry, B.P.; Hunter, T.J.; Tomcik, D.J.; O'Doherty, G.A. Org. Lett., 2005, 7, 745.
73. Xu, D.; Crispino, G.A.; Sharpless, K.B. J. Am. Chem. Soc., 1992, 114, 7570.
74. Ahmed, Md.M.; O'Doherty, G.A. J. Org. Chem., 2005, 70, 10576.
75. Li, M.; O'Doherty, G.A. Org. Lett., 2006, 8, 6087.
76. (a) Smith, C.M.; O'Doherty, G.A. Org. Lett., 2003, 5, 1959.
77. (b) Garaas, S.D.; Hunter, T.J.; O'Doherty, G.A. J. Org. Chem., 2002, 67, 2682.
78. Ahmed, Md.M.; O'Doherty, G.A. Tetrahedron Lett., 2005, 46, 4151.
79. (a) Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Synthesis, 1999, 2, 341.
80. (b) Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Chirality, 2000, 12, 338.
81. Achmatowicz, O.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Tetrahedron, 1971, 27, 1973.
82. (b) Takeuchi, M.; Nakamura, K.; Ogasawara, K. Synlett, 1996, 971.
83. Harris, J.M.; Keranen, M.D.; O'Doherty, G.A. J. Org. Chem., 1999, 64, 2982.
84. (b) Harris, J.M.; Keranen, M.D.; Nguyen, H.; Young, V.G.; O'Doherty, G.A. Carbohydr. Res., 2000, 328, 17.
85. (c) Babu, R.S.; O'Doherty, G.A. J. Am. Chem. Soc., 2003, 125, 12406.
86. Luche, J.-L. J. Am. Chem. Soc., 1978, 100, 2226.
87. Donohoe, T.J.; Blades, K.; Moore, P.R.; Waring, M.J.; Winter, J.J.G.; Helliwell, M.; Newcombe, N.J.; Stemp, G. J. Org. Chem., 2002, 67, 7946.
88. Haukaas, M.H.; O'Doherty, G.A. Org. Lett., 2002, 4, 1771.
89. Haukaas, M.H.; O'Doherty, G.A. Org. Lett., 2001, 3, 3899.
90. Guo, H.; O'Doherty, G.A. Tetrahedron, 2008, 64, 304.
91. Abrams, J.N.; Babu, R.S.; Guo, H.; Le, D.; Le, J.; Osbourn, J.M.; O'Doherty, G.A. J. Org. Chem., 2008, 73, 1935.
92. Guo, H.; O'Doherty, G.A. Org. Lett., 2005, 7, 3921.
93. See for example: Zhou, M.; O'Doherty, G.A. Curr. Top. Med. Chem., 2008, 8, 114.
94. (a) Guo, H.; O'Doherty, G.A. Angew. Chem. Int. Ed., 2007, 46, 5206.
95. (b) Guo, H.; O'Doherty, G. A. J. Org. Chem., 2008, 73, 5211.
96. Zhou, M.; O'Doherty, G.A. Org. Lett., 2006, 8, 4339.
97. (b) Zhou, M.; O'Doherty, G.A. J. Org. Chem., 2007, 72, 2485.
98. Babu, R.S.; Guppi, S.R.; O'Doherty, G.A. Org. Lett., 2006, 8, 1605.
99. (b) Guppi, S.R.; O'Doherty, G.A. J. Org. Chem., 2008, 72, 4966.
100. Jørgensen, K.A. Angew. Chem. Int. Ed., 2000, 39, 3558.
101. Osborn, H.M.I.; Coisson, D. Mini Rev. Org. Chem., 2004, 1, 41.
102. Zamojski, A. Preparative Carbohydrate Chemistry; Hanessian, S. Ed.; Marcel Dekker Inc.: New York, 1997; p. 615.
103. Auberson, Y.; Vogel, P. Helv. Chim. Acta, 1989, 72, 278.
104. See for example: (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc., 1993, 115, 7039.
105. (b) Mikami, K.; Motoyama, Y. Terada, M. J. Am. Chem. Soc., 1994, 116, 2812.
106. (c) Mikami, K.; Matsukawa, S. Nature, 1997, 385, 613.
107. Schaus, S.E.; Brånalt, J.; Jacobsen, E.N. J. Org. Chem., 1998, 63, 403.
108. See for example: Oi, S.; Terada, E.; Ohuchi, Y.; Kato, Y.; Tachibana, Y.; Inoue, Y. J. Org. Chem., 1999, 64, 8660.
109. Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R.G.; Jørgensen, K.A. J. Am. Chem. Soc., 1998, 120, 8599.
110. Jørgensen, K.A.; Johannsen, M.; Yao, S.; Audrain, H.; Thorhauge, J. Acc. Chem. Res., 1999, 32, 605.
111. (a) Evans, D.A.; Johnson, J.S. J. Am. Chem. Soc., 1998, 120, 4895.
112. (b) Evans, D.A.; Olhava, E.J.; Johnson, J.S.; Janey, J.M. Angew. Chem. Int. Ed., 1998, 37, 3372.
113. (c) Evans, D.A.; Johnson, J.S.; Olhava, E.J. J. Am. Chem. Soc., 2000, 122, 1635.
114. Johannsen, M.; Jørgensen, K.A.; Angew. Chem., Int. Ed., 1998, 37, 2404.
115. (b) Audrain, H.; Thorhauge, J.; Hazell, R.G.; Thorhauge, J.; Jorgensen, K.A. J. Org. Chem., 2000, 65, 4487.
116. Jurczak, J.; Chmielewski, M.; Filipek, S. Synthesis, 1979, 41. 2002, 18, 2707.
117. Malinowska, M.; Salanski, P.; Caille, J.-C.; Jurczak, J. Synthesis, 2002, 18, 2707.
118. Kwiatkowski, P.; Asztemborska, M.; Jurczak, J. Synlett, 2004, 10, 1755.
119. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis - From Biomimetic Concepts to Applications in Asymmetric Synthesis, Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2005.
120. (a) Córdova, A. Acc. Chem. Res., 2004, 37, 102.
121. (b) Gaunt, M.J.; Johansson, C.C.C.; McNally, A. Vo, N.T. Drug Discov. Today, 2007, 12, 8.
122. Kazmaier, U. Angew. Chem., Int. Ed., 2005, 44, 2186.
123. (b) Limbach, M. Chem. Biodiv., 2005, 2, 825.
124. (c) Sorensen, E- J.; Sammis, G. M. Science, 2004, 305, 1725.
125. Northrup, A.B.; MacMillan, D.W.C. J. Am. Chem. Soc., 2002, 124, 6798.
126. (b) Mangion, I.K.; Northrup, A.B.; MacMillan, D.W.C. Angew. Chem., Int. Ed., 2004, 43, 6722.
127. Northrup, A.B.; MacMillan, D.W.C. Science, 2004, 305, 1752.
128. Córdova, A.; Ibrahem, I.; Casas, J.; Sundén, H.; Engqvist, M.; Reyes, E. Chem. Eur. J., 2005, 11, 4772.
129. Córdova, A.; Engqvist, M.; Ibrahem, I.; Casas, J.; Sundèn, H. Chem. Commun., 2005, 2047.
130. Liao, W.-W.; Ibrahem, I.; Córdova, A. Chem. Commun., 2006, 674.
131. Mangion, I.K.; MacMillan, D.W.C. J. Am. Chem. Soc., 2005, 127, 3696.
132. For a recent example, see: Werz, D.B.; Seeberger, P.H. Angew. Chem., Int. Ed., 2005, 44, 6315.
133. Kulkarni, S.S.; Chi, F.-C.; Hung, S.-C. J. Chin. Chem. Soc., 2004, 51, 1193.
134. Hung, S.-C.; Puranik, R.; Chi, F.-C. Tetrahedron Lett., 2000, 41, 77.
135. Hung, S.-C.; Wang, C.-C.; Thopate, S.R. Tetrahedron Lett., 2000, 41, 3119.
136. Hung, S.-C.; Wang, C.-C.; Chang, S.-W.; Chen, C.-S. Tetrahedron Lett., 2001, 42, 1321.
137. (a) Hung, S.-C.; Thopate, S.R.; Chi, F.-C.; Chang, S.-W.; Lee, J.-C.; Wang, C.-C.; Wen, Y.-S. J. Am. Chem. Soc., 2001, 123, 3153.
138. (b) Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Fan, H.-F.; Pai, C.-L.; Yang, W.-C.; Lu, L.-D.; Hung, S.-C. Angew. Chem., Int. Ed., 2002, 41, 2360.
139. (a) Černý, M.; Stanek, J. Adv. Carbohydr. Chem. Biochem., 1977, 34, 23.
140. (b) Černý, M. Adv. Carb. Chem. Biochem., 2003, 58, 121.
141. Lu, L.-D.; Shie, C.-R.; Kulkarni, S.-S.; Pan, G.-R.; Lu, X.-A.; Hung, S.-C. Org. Lett., 2006, 8, 5995.
142. (a) Takahashi, H.; Shida, T.; Hitomi, Y.; Iwai, Y.; Ikegami, S. J. Am. Chem. Soc., 2000, 122, 2995.
143. (b) Takahashi, H.; Shida, T.; Hitomi, Y.; Iwai, Y.; Miyama, N.; Nishiyama, K.; Sawada, D.; Ikegami, S. Chem. Eur. J., 2006, 12, 5868.
144. In spite of its broad use in organic synthesis, this procedure represents the first application of the Mitsunobu-type cyclization devoted to the synthesis of carbohydrates.
145. Boulineau, F.P.; Wei, A. Org. Lett., 2002, 4, 2281.
146. Philips, K.D.; Zemlicka, J.; Horwitz, J.P. Carbohydr. Res., 1973, 30, 281.
147. Fleming, I.; Sanderson, P.E.J. Tetrahedron Lett., 1987, 28, 4229.
148. Boulineau, F.P.; Wei, A. J. Org. Chem., 2004, 69, 3391.
149. Boulineau, F.P.; Wei, A. Org. Lett., 2004, 6, 119.
150. (a) Davis, B.G.; Boyer, V. Nat. Prod. Rep., 2001, 18, 618.
151. (b) Koeller, K.M.; Wong, C.-H. Nature, 2001, 409, 232.
152. Sukumaran, J.; Hanefeld, U. Chem. Soc. Rev., 2005, 34, 530.
153. Keasling, J.D. ACS Chem. Biol., 2008, 3, 64.
154. Hult, K.; Berglund, P. Curr. Opin. Biotech., 2003, 14, 395.
155. (a) Wong, C.-H.; Halcomb, R.L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed., 1995, 34, 412.
156. (b) Gijsen, H.J.M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev., 1996, 96, 443.
157. (c) Takayama, S.; McGarvey, G.J.; Wong, C.-H. Chem. Soc. Rev., 1997, 26, 407.
158. (d) Machajewsky, T.D.; Wong, C.-H. Angew. Chem., Int Ed., 2000, 39, 1352.
159. During the last years new technologies have been further implemented to increase scope and practicality of aldolases as tools for the synthetic chemist, including the discovery of new classes of aldolases: (a) Silvestri, M.G.; Desantis, G.; Mitchell M.; Wong, C.-H. Top. Stereochem., 2003, 23, 267.
160. (b) Dean, S.M.; Greenberg, W.A.; Wong, C.-H. Adv. Synth. Catal., 2007, 349, 1308.
161. Further deepening on the use of aldolases for monosaccharide synthesis is not the purposes of this review, as the synthetic target reached by aldolases diverges from the one herein discussed.
162. (a) Izumori, K. Naturwissenschaften, 2002, 89, 120.
163. (b) Izumori, K. J. Biotech., 2006, 124, 717.
164. Ito, H.; Okaya, H.; Khan, A.R.; Tajima, S.; Hayakawa, S.; Izumori, K. Biosci. Biotechnol. Biochem., 1994, 2168.
165. Takeshita, K.; Suga, A.; Takada, G.; Izumori, K. J. Biosci. Bioeng., 2000, 453.
166. Ito, H.; Izumori, K. J. Ferment. Bioeng., 1996, 351.
167. Shimonishi, T.; Okumura, Y.; Izumori, K. J. Ferment. Bioeng., 1995, 620.
168. (a) Sasahara, H.; Mine, M.; Izumori, K. J. Ferment. Bioeng., 1998,
169. (b) Sasahara, H.; Izumori, K. J. Biosci. Bioeng., 1999, 548.
170. One of the first approaches to monosaccharides can be considered the classical 1861 formose synthesis from formaldehyde: Boutlerow, M.A. Compt. Rend., 1861, 53, 145.