Vitamin B12 and α-ribonucleosides

Tetrahedron

Volumn 64, Issue 1, 2008, Pages 9-38

  Chandra, Tilak ^a   Brown, Kenneth L ^a  

^a OHIO UNIVERSITY   (United States)

Author keywords

Ribonucleoside; Co enzyme; Glycosylation; Guided biosynthesis; Vitamin B12

Indexed keywords

2 FLUORO 1 METHYLPYRIDINIUM TOSYLATE; 5,6 DIMETHYLBENZIMIDAZOLE; ALPHA INDOLINE; ALPHA RIBONUCLEOSIDE; BENZIMIDAZOLE; BORON; COBALAMIN DERIVATIVE; CYANOCOBALAMIN; INDOLE DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE; STANNIC CHLORIDE; TOLUENESULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ANALYTIC METHOD; BIOSYNTHESIS; CATALYSIS; DEPROTECTION REACTION; ENZYME ISOLATION; EPIMERIZATION; GLYCOSYLATION; PHOTOLYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; X RAY ANALYSIS;

EID: 36348981012     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.08.061     Document Type: Review

References (157)

1. Brown K.L. Chem. Rev. 105 (2005) 2075-2149
2. Brown K.L. Dalton Trans. (2006) 1123-1133
3. Hamza M.S.A., Zou X., Banka R., Brown K.L., and van Eldik R. Dalton Trans. 4 (2005) 782-787
4. Brown K.L., and Li J. J. Am. Chem. Soc. 120 (1998) 9466-9474
5. Brown K.L., Cheng S., Zou X., Li J., Chen G., Valente E.J., Zubkowski J.D., and Marques H.M. Biochemistry 37 (1998) 9704-9715
6. Booker S., and Stubbe J. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 8352-8356
7. Babior B.M., Carty T.J., and Abeles R.H. J. Biol. Chem. 249 (1974) 1689-1695
8. Marsh E., and Neil G. Bioorg. Chem. 28 (2000) 176-189
9. Hodgkin D.C., Kamper J., Mackay M., and Pickworth J. Nature 178 (1956) 64-66
10. Kräutler B., Konrat R., Stupperich E., Färber G., Gruber K., and Kratky C. Inorg. Chem. 33 (1994) 4128-4139
11. Fasching M., Schmidt W., Kräutler B., Stupperich E., Schmidt A., and Kratky C. Helv. Chim. Acta 83 (2000) 2295
12. Randaccio L., Furlan M., Geremia S., Slouf M., Srnova I., and Toffoli D. Inorg. Chem. 39 (2000) 3403-3413
13. Renz P. Methods Enzymol. 18C (1971) 82-92
14. Hörig J.A., Renz P., and Heckmann G. J. Biol. Chem. 253 (1978) 7410-7414
15. Stupperich E., Steiner I., and Rühlemann M. Anal. Biochem. 155 (1986) 365-370
16. Chandra T., and Brown K.L. Nucleosides Nucleotides Nucleic Acids 26 (2007) 1-8
17. Chandra T., Zou X., Valente E.J., and Brown K.L. J. Org. Chem. 71 (2006) 5000-5003
18. Kumar P., Chandra T., Zou S., and Brown K.L. J. Phys. Chem. 110 (2006) 5-8
19. Chandra T., and Brown K.L. Tetrahedron Lett. 46 (2005) 2071-2074
20. Brown K.L., Chandra T., Zou S., and Valente E.J. Nucleosides Nucleotides Nucleic Acids 24 (2005) 1147-1165
21. Chandra T., and Brown K.L. Tetrahedron Lett. 46 (2005) 8617-8619
22. Chandra T., Zou X., and Brown K.L. Tetrahedron Lett. 45 (2004) 7783-7786
23. Mukaiyama T., Hashimoto Y., Hayashi Y., and Shoda S.I. Chem. Lett. (1984) 557-560
24. Chu C.K., and Baker D.C. Nucleosides Nucleotides as Antitumor and Antiviral Agents (1993), Plenum, New York, NY
25. In: Schinazi R.F., and Liotta D.C. (Eds). Frontiers in Nucleosides and Nucleic Acids (2004), IHL, Georgia
26. In: Chu C.K. (Ed). Recent Advances in Nucleosides: Chemistry and Chemotherapy (2002), Elsevier Science, New York, NY
27. LePage G.A., and Khaliq A. Cancer Treat. Rep. 63 (1979) 53-57
28. Friedrich W., Gross G., Bernhauer K., and Zeller P. Helv. Chim. Acta 43 (1960) 704-712
29. 12 (1999), John Wiley and Sons, New York, NY 921
30. Bagnato J.D., Eilers A.L., Horton R.A., and Grissom C.B. J. Biochem. 69 (2004) 8987-8996
31. Howard Jr. W.A., Bayomi A., Natarajan E., Aziza M.A., el-Ahmady O., Grissom C.B., and West F.G. Bioconjugate Chem. 8 (1997) 498-502
32. Mitchell A.M., Bayomi A., Natarajan E., Barrows L.R., West F.G., and Grissom C.B. Enzym. Mech. 27 (1999) 150-154
33. Bayomi A.H., Mitchell A.M., Natarajan E.N., Grissom C.B., West F.G., Aziza M.A., and El-Ahmady O. Abstracts of Papers. 214th National Meeting of the American Chemical Society, Las Vegas, NV, 7-11 September 1997 (1996), American Chemical Society, Washington, DC MEDI-123
34. Bayomi, A. H.; Mitchell, A. M.; Natarajan, E. N.; Grissom, C. B.; West, F. G.; Aziza, M. A.; El-Ahmady, O. Abstracts of Papers. 213th National Meeting of the American Chemical Society, San Francisco, CA, 13-17 April 1997; American Chemical Society: Washington, DC, MEDI-123.
35. Morgan, A. C; Wilbur, D. S; Pathare, P. M. PCT Int. Appl., 1995; 101, WO 9527723.
36. Forbes C.L., and Franck R.W. J. Org. Chem. 64 (1999) 1424-1425
37. Brodie J.D. Proc. Natl. Acad. Sci. U.S.A. 62 (1969) 461-467
38. Grate J.H., and Schrauzer. J. Am. Chem. Soc. 101 (1979) 4601-4611
39. Kleban M., Kautz U., Greul J., Hilgers P., Kugler R., Dong H.-Q., and Jäger V. Synthesis (2000) 1027
40. Petrovic Z.D., Andelkovic D., and Stevanovic L. J. Serb. Chem. Soc. 68 (2003) 719-722
41. Gantzer C.J., and Wackett L.P. Environ. Sci. Technol. 25 (1991) 715-722
42. Habeck B.D., and Sublette K.L. Appl. Biochem. Biotechnol. 51/52 (1995) 747-759
43. Lesage S., Brown S., and Millar K. Ground Water Monit. Rem. 16 (1996) 76-85
44. Glod G., Angst W., Holliger C., and Schwarzenbach R.P. Environ. Sci. Technol. 31 (1997) 253-260
45. Burris D.R., Delcomyn C.A., Smith M.H., and Roberts A.L. Environ. Sci. Technol. 30 (1996) 3047-3052
46. Burris D.R., Delcomyn C.A., Deng B.L., Buck L.E., and Hatfield K. Environ. Toxicol. Chem. 17 (1998) 1681-1688
47. Semadeni M., Chiu P.C., and Reinhard M. Environ. Sci. Technol. 32 (1998) 1207-1213
48. Shey J., and van der Donk W.A. J. Am. Chem. Soc. 122 (2000) 12403-12404
49. McCauley K.M., Wilson S.R., and van der Donk W. J. Am. Chem. Soc. 125 (2003) 4410-4411
50. Pratt D.A., and van der Donk W.A. Chem. Commun. (2006) 558-560
51. Folkers K. In: Dolphin D. (Ed). B12 (1982), Wiley, New York, NY 1
52. Chandra, T.; Brown, K. L. Unpublished results.
53. Brown K.L., Zou X., Banka R.R., Perry C.B., and Merques H.M. Inorg. Chem. 43 (2004) 8130-8142
54. Guided biosynthesis failed because the biosynthetic process could not incorporate the desired indole base or α-indole ribonucleosides in the structure, the reason is still unknown.
55. Toraya T., and Ishida A. J. Biol. Chem. 266 (1991) 5430-5437
56. Fukuoka M., Yamada S., Miyoshi S., Yamashita K., Yamanishi M., Zou X., Brown K.L., and Toraya T. J. Biochem. 132 (2002) 935-943
57. Brown K.L., Zou X., Li J., and Chen G. Inorg. Chem. 40 (2001) 5942-5947
58. Marzilli L.G., Toscano J., Randaccio L., Bresciani-Pahor N., and Calligaris M. J. Am. Chem. Soc. 101 (1979) 6754-6756
59. See Ref. 21c.
60. 12 Vol. 1 (1982), Wiley, New York, NY
61. Brown K.L., and Brooks H.B. Inorg. Chem. 30 (1991) 3420-3430
62. Brown K.L., and Marques H.M. Theochem 714 (2005) 209-215
63. Lenhert P.G. Proc. R. Soc. London, Ser. A 303 (1968) 45-84
64. Savage H.F.J., Leadley P.F., Finney J.L., and Timmons P.A. Acta Crystallogr., Sect. B 43 (1987) 280-295
65. Woodward R.B. Pure Appl. Chem. 17 (1968) 519-547
66. Woodward R.B. Pure Appl. Chem. 25 (1971) 283-304
67. Woodward R.B. Pure Appl. Chem. 33 (1973) 145-177
68. Bonnett R., Godfrey J.M., and Redman D.G. J. Chem. Soc. C8 (1963) 1163
69. Riether D., and Mulzer J. Eur. J. Org. Chem. (2003) 30-45
70. Bonnett R. Chem. Rev. 6 (1963) 573-605
71. Holly F.W., Shunk C.H., Peel E.W., Cahill J.H., Lavigne J.B., and Folkers K. J. Am. Chem. Soc. 74 (1952) 4521-4525
72. Stevens J.D., Ness R.K., and Fletcher Jr. H.G. J. Org. Chem. 33 (1968) 1806-1810
73. Kuzuhara H., and Hewitt Jr. G. J. Org. Chem. 33 (1968) 1816-1819
74. Butler P.A., Elbert M.O., Lyskowski A., Gruber K., Kratky C., and Krautler B. Angew. Chem., Int. Ed. 45 (2005) 989-993
75. Townsend L.B. Chemistry of Nucleosides and Nucleotides (1988), Springer, New York, NY
76. Townsend L.B. Chemistry of Nucleosides and Nucleotides (1994), Springer, New York, NY
77. Vorbrüggen H., and Ruh-Pohlenz C. Handbook of Nucleoside Synthesis (2001), Wiley-Interscience, New York, NY
78. Fischer E., and Helferich B. Chem. Ber. 47 (1914) 210-235
79. Hilbert G.E., and Johnson T.B. J. Am. Chem. Soc. 52 (1930) 4489-4494
80. Davoll J., and Lowy B.A. J. Am. Chem. Soc. 73 (1951) 1650-1655
81. Ishido Y., and Sato T. Bull. Chem. Soc. Jpn. 34 (1961) 1347-1348
82. Seela F., and Winkeler H.-D. J. Org. Chem. 47 (1982) 226-230
83. Ugarkar B.G., Castellino A.J., DaRe J.M., Kopcho J.J., Wiesner J.B., Schanzer J.M., and Erion M.D. J. Med. Chem. 43 (2000) 2894-2905
84. Kazimierczuk Z., Cottam H.B., Revankar G.R., and Robins R.K. J. Am. Chem. Soc. 106 (1984) 6379-6382
85. Kandasamy R., Imamura N., Robins R.K., and Revankar G.R. Tetrahedron Lett. 28 (1987) 5107-5110
86. Cottam H.B., Petrie C.R., McKernan P.A., Goebel R.J., Dalley N.K., Davidson R.B., Robins R.K., and Revankar G.R. J. Med. Chem. 27 (1984) 1119-1127
87. Vorbrüggen H., Krolikiewicz K., and Bennua B. Chem. Ber. 114 (1981) 1234-1255
88. Cousineau T.J., and Secrist III J.A. J. Org. Chem. 44 (1979) 4351-4358
89. Hollingsworth R.I., and Wang G. Chem. Rev. 100 (2000) 4267-4282
90. Wong C.-H., and Kathryn K.M. Chem. Rev. 100 (2000) 4465-4494
91. Koji O., and Hisoshi W. Yakugaku Zasshi 83 (1963) 890-891
92. Hideyuki, S.; Kenji, O. Jpn. Kokai Kokkyo Koho JP 06263791, 1994.
93. Furukawa Y., ichi K., and Honjo M. Tetrahedron Lett. 45 (1968) 4655-4658
94. Wright R.S., Tener G.M., and Khorana H.G. J. Am. Chem. Soc. 80 (1958) 2004-2006
95. Prisbe E.J., Verheyden J.P.H., and Moffatt J.G. J. Org. Chem. 43 (1978) 4784-4794
96. Mikhailov S.N., and Pfleiderer W. Synthesis 4 (1985) 397-399
97. Kiss J., and D'Souza R. J. Carbohydr. Nucleosides Nucleotides 7 (1980) 141-157
98. Riley T.A., Larsen S.B., Avery T.L., Finch R.A., and Robins R.K. J. Med. Chem. 33 (1990) 572-576
99. Sweeney D.L., Gearien J.E., Bauer L., and Currie B.L. J. Carbohydr. Nucleosides Nucleotides 6 (1979) 387-409
100. Janardhanam S., and Nambiar K.P. Tetrahedron Lett. 35 (1994) 3657-3660
101. Baud M.V., Chavis C., Lucas M., and Imbach J.-L. Tetrahedron Lett. 31 (1990) 4437-4440
102. Mukaiyama T., Hayashi Y., and Hashimoto Y. Chem. Lett. (1985) 1087-1090
103. Trost B.M., and Nubling C. Carbohydr. Res. 202 (1990) 1-12
104. Reitz A.B., and Rebarchak M.C. Nucleosides Nucleotides 11 (1992) 1115-1121
105. Okamoto, K.; Goto, T. JP 61207400, 1986.
106. Seley K.L., Salim S., and Zhang L. Org. Lett. 7 (2005) 63-66
107. Seley K.L., Salim S., Zhang L., and O'Daniel P.I. J. Org. Chem. 70 (2005) 1612-1619
108. Kirk K.L., Nagai W., and Cohen L.A. J. Am. Chem. Soc. 95 (1973) 8389-8392
109. Kirk K.L., and Cohen L.A. J. Org. Chem. 38 (1973) 3647-3648
110. Chandra, T.; Brown, K. L. Unpublished work.
111. Tyson F.T. J. Am. Chem. Soc. 63 (1941) 2024-2025
112. Leo M.O., and Catharine O.W. Can. J. Res. 25B (1947) 1-13
113. Gribble G.W., and Hoffman J.H. Synthesis 12 (1977) 859-860
114. Fox P.A., Gray S.D., Bruck M.A., and Wigley D.E. Inorg. Chem. 35 (1996) 6027-6036
115. Preobrazhenskaya M.N., Yartseva I.V., and Ektova L.V. Nucleic Acid Chem. 2 (1978) 721-623
116. Preobrazhenskaya M.N., Vigdorchik M.N., and Suvorov N.N. Tetrahedron 23 (1967) 4653-4660
117. Sato Y., Tateno G., Seio K., and Sekine M. Tetrahedron Lett. 43 (2002) 3251-3254
118. Morvan F., Rayner B., Imbach J.-L., Chang D.-K., and Lown J.W. Nucleic Acids Res. (1986) 5019-5035
119. Morvan F., Rayner B., Imbach J.-L., Thenet S., Bertrand J.-R., Paoletti J., Malvy C., and Paoletti C. Nucleic Acids Res. (1987) 3421-3437
120. Cazenova C., Chevrier M., Thuong N.T., and Hélène C. Nucleic Acids Res. (1987) 10507-10521
121. Morvan F., Rayner B., Imbach J.-L., Lee M., Hartley J.A., Chang D.-K., and Lown J.W. Nucleic Acids Res. (1987) 7027-7044
122. Gagnor C., Rayner B., Leonetti J.-P., Imbach J.-L., and Lebleu B. Nucleic Acids Res. (1989) 5107-5114
123. Sun J.S., Giovannangeli C., Francois J.C., Kurfurst R., Garestier T.M., Asseline U., Behmoaras T.S., Thuong N.T., and Hélène C. Proc. Natl. Acad. Sci. U.S.A. (1991) 6023-6027
124. García J., Díaz-Rodríguez A., Fernndez S., Sanghvi Y.S., Ferrero M., and Gotor V. J. Org. Chem. 71 (2006) 9765-9771
125. Greene T.W., and Wuts P.G.M. Protective groups in organic synthesis. 3rd ed. (1999), Wiley, New York, NY
126. Wang P., Gullen B., Newton M.G., Cheng Y.-Chi., Schinazi R.F., and Chu C.K. J. Med. Chem. 42 (1999) 3390-3399
127. Bessodes M., Komiotis D., and Antonakis K. Tetrahedron Lett. 27 (1986) 579-582
128. MacCoss M., and Cameron D.J. Carbohydr. Res. 60 (1978) 206-209
129. Brown K.L., Evans D.R., Zubkowski J.D., and Valente E.J. Inorg. Chem. 35 (1996) 415-423
130. Kratky C., Fräber G., Gruber K., Wilson K., Dauter Z., Nolting H.-F., Konrat R., and Kräutler B. J. Am. Chem. Soc. 117 (1995) 4654-4670
131. Calafat A.M., Taoka S., Puckett Jr. J.M., Semerad C., Yan H., Luo L., Chen H., Banerjee R., and Marzilli L.G. Biochemistry 34 (1995) 14125-14130
132. Calafat A.M., and Marzilli L.G. J. Am. Chem. Soc. 115 (1993) 9182-9190
133. Pagano T.G., Marzilli L.G., Flocco M.M., Tsai C., Carrell H.L., and Glusker J.P. J. Am. Chem. Soc. 113 (1991) 531-542
134. Pagano T.G., and Marzilli L.G. Biochemistry 28 (1989) 7213-7223
135. Pagano T.G., Yohannes P.G., Hay B.P., Scott J.R., Finke R.G., and Marzilli L.G. J. Am. Chem. Soc. 111 (1989) 1484-1491
136. Brown K.L., and Hakimi J.M. J. Am. Chem. Soc. 108 (1986) 496-503
137. Townsend L.B. Synthetic Procedures in Nucleic Acid Chemistry Vol II (1973), Wiley Interscience, New York, NY pp 267-398
138. Chu C.K., Kabbani-EI F.M., and Thompson B.B. Nucleosides Nucleotides 3 (1984) 1-31
139. Imbach J.L. Ann. N.Y. Acad. Sci. 255 (1975) 177-184
140. Rayner B., Tapiero C., and Imbach J.L. Carbohydr. Res. 47 (1976) 195-202
141. Imbach J.L., Barascut J.L., Kam B.L., Rayner B., Tamby C., and Tapiero C. J. Heterocycl. Chem. 10 (1973) 1069-1070
142. Imbach J.L., Barascut J.L., Kam B.L., and Tapiero C. Tetrahedron Lett. 2 (1974) 129-130
143. Ravindranathan S., Kim C.H., and Bodenhausen G. J. Biomol. NMR 27 (2003) 365-375
144. Kumar A., Grace R.C.R., and Madhu P.K. Prog. NMR Spect. 37 (2000) 191-319
145. Fushman D., and Cowburn D. Methods Enzymol. 339 (2001) 109-126
146. Levitt M.H., and DiBari L. Phys. Rev. Lett. 69 (1992) 3124-3127
147. Wang T., Cai S., and Zuiderweg E.R.P. J. Am. Chem. Soc. 125 (2003) 8639-8643
148. Dittmer J., Kim C.-H., and Bodenhausen G. J. Biomol. NMR 26 (2003) 259-275
149. Pervushin K.V., Riek R., Wider G., and Wüthrich K. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 12366-12371
150. Fischer M.W.F., Zeng L., Majumdar A., and Zuiderweg E.R.P. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 8016-8019
151. Kumar P., and Kumar A. J. Magn. Reson., Ser. A 115 (1995) 155-164
152. Kumar P., and Kumar A. J. Magn. Reson., Ser. A 119 (1996) 29-37
153. Werbelow L.G. J. Phys. Chem. 94 (1990) 6663-6666
154. Tjandra N., and Bax A. J. Am. Chem. Soc. 119 (1997) 8076-8082
155. Dalvit C., and Bodenhausen G. Chem. Phys. Lett. 161 (1989) 554-560
156. Plavec J., Roselt P., Földesi A., and Chattopadhyaya J. Magn. Reson. Chem. 36 (1998) 732
157. Altona C., and Sundaralingam M. J. Am. Chem. Soc. 95 (1973) 2333-2344