Complementary Routes to Natural Product Glycodiversification: Pathway Engineering and Glycorandomization

Comprehensive Glycoscience: From Chemistry to Systems Biology

Volumn 3-4, Issue , 2007, Pages 373-396

  Thibodeaux, C J ^a   Liu, H W ^a   Thorson, J S ^b  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57549114884     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-044451967-2/00040-4     Document Type: Chapter

References (111)

1. Newman D.J., Cragg G.M., Snader K.M. J. Nat. Prod. 2003, 66:1022-1037.
2. Butler M.S. J. Nat. Prod. 2004, 67:2141-2153.
3. Koehn F., Carter G.T. Nat. Rev. Drug. Discov. 2005, 4:206-220.
4. Weymouth-Wilson A.C. Nat. Prod. Rep. 1997, 14:99-110.
5. Thorson J.S., Hosted T.J., Jiang J., Biggins J.B., Ahlert J. Curr. Org. Chem. 2001, 5:139-167.
6. Carbohydrate-Based Drug Discovery 2003, Wiley-VCH, Weinheim, Germany.
7. Pelzer S., Vente A., Bechthold A. Curr. Opin. Drug Discov. Devel. 2005, 8:228-238.
8. Mendez C., Salas J.A. Microb. Process. Prod. 2005, 18:131-148.
9. Griffith B.R., Langenhan J.M., Thorson J.S. Curr. Opin. Biotechnol. 2005, 16:622-630.
10. Pindur U., Kim Y.-S., Mehrabani F. Curr. Med. Chem. 1999, 6:29-69.
11. Prudhomme M. Curr. Med. Chem. 2000, 7:1189-1212.
12. Long B.H., Balasubramanian B.N. Expert Opin. Ther. Patents 2000, 10:635-666.
13. Bailly C. Curr. Med. Chem. 2000, 7:39-58.
14. Prudhomme M. Eur. J. Med. Chem. 2003, 38:123-140.
15. Moreau P., Gaillard N., Marminon C., Anizon F., Dias N., Baldeyrou B., Bailly C., Pierre A., Hickman J., Pfeiffer B., Renard P., Prudhomme M. Bioorg. Med. Chem. 2003, 11:4871-4879.
16. Carrasco C., Facompre M., Chisholm J.D., Van Vranken D.L., Wilson W.D., Bailly C. Nucleic Acids Res. 2002, 30:1774-1781.
17. Zhang G., Shen J., Cheng H., Zhu L., Fang L., Luo S., Muller M.T., Lee G.E., Wei L., Du Y., Sun D., Wang P.G. J. Med. Chem. 2005, 48:2600-2611.
18. Saulnier M.G., Balasubramanian B.N., Long B.H., Frennesson D.B., Ruediger E., Zimmermann K., Eummer J.T., St. Laurent D.R., Stoffan K.M., Naidu B.N., Mahler M., Beaulieu F., Bachand C., Lee F.Y., Fairchild C.R., Stadnick L.K., Rose W., Solomon C., Wong H., Martel A., Wright J.J., Kramer R., Langley D.R., Vyas D.M. J. Med. Chem. 2005, 48:2258-2261.
19. Arcamone F. Doxorubicin Anticancer Antibiotics; Medicinal Chemistry. A Series of Monographs 1981, Academic Press, New York.
20. Gewirtz D.A. Biochem. Pharmacol. 1999, 57:727-741.
21. Arcamone F.M. Biochimie 1998, 80:201-206.
22. Binaschi M., Bigioni M., Cipollone A., Rossi C., Goso C., Maggi C.A. Curr. Med. Chem. 2001, 1:113-130.
23. Temperini C., Messori L., Orioli P., Di Bugno C., Animati F., Ughetto G. Nucleic Acids Res. 2003, 31:1464-1469.
24. Larsen A.K., Escargueil A.E., Skladanowski A. Pharmacol. Therapeut. 2003, 99:167-181.
25. Schimmel K.J.M., Richel D.J., van den Brink R.B.A., Guchelaar H.J. Cancer Treat. Rev. 2004, 30:181-191.
26. Bililign T., Griffith B.R., Thorson J.S. Nat. Prod. Rep. 2005, 22:742-760.
27. Rohr J., Zeeck A. J. Antibiot. 1990, 43:1169-1178.
28. Lombo F., Gibson M., Greenwell L., Brana A.F., Rohr J., Salas J.A., Mendez C. Chem. Biol. 2004, 11:1709-1718.
29. Poehlsgaard J., Douthwaite S. Nat. Rev. Microbiol. 2005, 3:870-881.
30. Yonath A. Annu. Rev. Biochem. 2005, 74:649-679.
31. Katz L., Ashley G.W. Chem. Rev. 2005, 105:499-528.
32. Champney W.S. Curr. Top. Med. Chem. 2003, 3:929-947.
33. Bonay P., Duranchica I., Fresno M., Alarcon B., Alcina A. Antimicrob. Agents Chemother. 1998, 42:2668-2673.
34. Jose E.S., Munozfernandez M.A., Alarcon B. Virology 1997, 239:303-314.
35. Bonay P., Fresno M., Alarcon B. J. Cell Sci. 1997, 110:1839-1849.
36. Bonay P., Munro S., Fresno M., Alarcon B. J. Biol. Chem. 1996, 271:3719-3726.
37. Nicolaou K.C., Boddy C.N.C., Brase S., Winssinger N. Angew. Chem., Int. Ed. 1999, 38:2096-2152.
38. Boger D.L. Med. Res. Rev. 2001, 21:356-381.
39. Malabarba A., Ciabatti R. Curr. Med. Chem. 2001, 8:1759-1773.
40. Sussmith R.D. Chem. BioChem. 2002, 3:295-298.
41. Allen N.E., Nicas T.I. FEMS Microbiol. Rev. 2003, 26:511-532.
42. Walsh C. Antibiotics Actions, Origins, Resistance 2003, ASM Press, Washington, DC.
43. Preobrazhenskaya M.N., Olsufyeva E.N. Expert Opin. Ther. Patents 2004, 14:141-173.
44. Kahne D., Leimkuhler C., Lu W., Walsh C. Chem. Rev. 2005, 105:395-448.
45. Weizel P. Chem. Rev. 2005, 105:4610-4660.
46. Mehanna A.S. Cardiac agents. Principles of Medicinal Chemistry 1995, 366-371. Lippincott, Williams & Wilkins, Philadelphia. W.O. Foye, T.L. Lemke, D.A. Williams (Eds.).
47. Kjeldsen K., Norgaard A., Gheorghiade M. Cardiovasc. Res. 2002, 55:710-713.
48. Thorson J.S., Vogt T. Carbohydrate-Based Drug Discovery 2003, 685-711. Wiley-VCH, New York.
49. Stenkvist B. Oncol. Rep. 1999, 493-496.
50. Haux J. Med. Hypotheses 1999, 53:543-548.
51. Hauptman P.J., Garg R., Kelly R.A. Prog. Cardiovasc. Dis. 1999, 41:247-254.
52. Stenkvist B. Anti-Cancer Drugs 2001, 12:635-636.
53. Haux J. Med. Hypotheses 2002, 59:781-782.
54. Wasserstrom J.A., Aistrup G.L. Am. J. Physiol. Heart Circ. Physiol. 2005, 289:H1781-H1793.
55. Kramer P.J., Khosla C. Ann. NY Acad. Sci. 1996, 799:32-45.
56. Khosla C., Zawada R.J. Trends Biotechnol. 1996, 14:335-341.
57. Hopwood D.A., Sherman D.H. Annu. Rev. Genet. 1990, 24:37-66.
58. Katz L., Donadio S. Annu. Rev. Microbiol. 1993, 47:875-912.
59. Hutchinson C.R., Fujii I. Annu. Rev. Microbiol. 1995, 49:201-238.
60. Carreras C.W., Pieper R., Khosla C. Bioorganic Chemistry: Deoxysugars, Polyketides & Related Classes: Synthesis, Biosynthesis, Enzymes 1997, 85-126. Springer, Berlin, Germany. J. Rohr (Ed.).
61. Menzella H.G., Reid R., Carney J.R., Chandran S.S., Reisinger S.J., Patel K.G., Hopwood D.A., Santi D.V. Nat. Biotechnol. 2005, 23:1171-1176.
62. Weissman K.J., Leadlay P.F. Nat. Rev. Microbiol. 2005, 3:925-936.
63. Yoon Y.J., Beck B.J., Kim B.S., Kang H.-Y., Reynolds K.A., Sherman D.H. Chem. Biol. 2002, 9:203-214.
64. Staunton J., Wilkinson B. Curr. Opin. Chem. Biol. 2001, 5:159-164.
65. Solenberg P., Matsushima P., Stack D.R., Wilkie S.C., Thompson R.C., Baltz R.H. Chem. Biol. 1997, 4:195-202.
66. Madduri K., Kennedy J., Rivola G., Inventi-Solari A., Filippini S., Zanuso G., Colombo A.L., Gewain K.M., Occi J.L., MacNeil D.J., Hutchinson C.R. Nat. Biotechnol. 1998, 16:69-74.
67. Omura S. Macrolide Antibiotics, Chemistry, Biology, and Practice 1984, Academic Press, New York.
68. Zhao L., Sherman D.H., Liu H.-w. J. Am. Chem. Soc. 1998, 120:10256-10257.
69. Zhao L., Que N.L.S., Xue Y., Sherman D.H., Liu H.-w. J. Am. Chem. Soc. 1998, 120:10259-10260.
70. Borisova S.A., Zhao L., Sherman D.H., Liu H.-w. Org. Lett. 1999, 1:133-136.
71. Zhao L., Borisova S., Yeung S.-m., Liu H.-w. J. Am. Chem. Soc. 2001, 123:7909-7910.
72. Yamase H., Zhao L., Liu H.-w. J. Am. Chem. Soc. 2000, 122:12397-12398.
73. Pisowotzki K., Mansori K., Piepersberg M. Mol. Gen. Genet. 1991, 231:113-123.
74. Distler J., Mansouri K., Mayer G., Stockmann M., Piepersberg W. Gene 1992, 115:105-111.
75. Borisova S.A., Zhao L., Melancon C.E., Kao C.-L., Liu H.-w. J. Am. Chem. Soc. 2004, 126:6534-6535.
76. Melancon C.E., Yu W.-L., Liu H.-w. J. Am. Chem. Soc. 2005, 127:12240-12241.
77. Chen H., Yamase H., Murakami K., Chang C.-w., Zhao L., Zhao Z., Liu H.-w. Biochemistry 2002, 41:9165-9183.
78. Anzai Y., Saito N., Tanaka M., Kinoshita K., Koyama Y., Kato F. FEMS Microbiol. Lett. 2003, 218:135-141.
79. Rohr J., Thiericke R. Nat. Prod. Rep. 1992, 9:103-137.
80. Krohn K., Rohr J. Top. Curr. Chem. 1997, 188:127-195.
81. Drautz H., Zahner H., Rohr J., Zeeck A. J. Antibiot. 1986, 39:1657-1669.
82. Rohr J., Beale J.M., Floss H.G. J. Antibiot. 1989, 42:1151-1157.
83. Rohr J., Schonewolf M., Udvarnoki G., Eckardt K., Schumann G., Wagner C., Beale J.M., Sorey S.D. J. Org. Chem. 1993, 58:2547-2551.
84. Decker H., Haag S. J. Bacteriol. 1995, 177:6126-6136.
85. Kunzel E., Faust B., Oelkers C., Weissbach U., Bearden D.W., Weitnauer G., Westrich L., Bechtold A., Rohr J. J. Am. Chem. Soc. 1999, 121:11058-11062.
86. Trefzer A., Hoffmeister D., Kunzel E., Stockert S., Weitnauer G., Westrich L., Rix U., Fuchser J., Bindseil K.U., Rohr J., Bechtold A. Chem. Biol. 2000, 7:133-142.
87. Hoffmeister D., Ichinose K., Domann S., Faust B., Trefzer A., Drager G., Kirschning A., Fischer C., Kunzel E., Bearden D.W., Rohr J., Bechtold A. Chem. Biol. 2000, 7:821-831.
88. Drautz H., Reuschenbach P., Zahner H., Rohr J., Zeeck A. J. Antibiot. 1985, 38:1291-1301.
89. Decker H., Haag S., Udvarnoki G., Rohr J. Angew. Chem., Int. Ed. Engl. 1995, 34:1107-1110.
90. Decker H., Rohr J., Motamedi H., Zahner H., Hutchinson C.R. Gene 1995, 166:121-126.
91. Wohlert S.-E., Blanco G., Lombo F., Fernandez E., Brana A.F., Reich S., Udvarnoki G., Mendez C., Decker H., Frevert J., Salas J.A., Rohr J. J. Am. Chem. Soc. 1998, 120:10596-10601.
92. Prado L., Fernandez E., Weissbach U., Blanco G., Quiros L.M., Brana A.F., Mendez C., Rohr J., Salas J.A. Chem. Biol. 1999, 6:19-30.
93. Blanco G., Patallo E.P., Brana A.F., Trefzer A., Bechtold A., Rohr J., Mendez C., Salas J.A. Chem. Biol. 2001, 8:253-263.
94. Sanchez C., Zhu L., Brana A.F., Salas A.P., Rohr J., Mendez C., Salas J.A. Proc. Natl. Acad. Sci. USA 2005, 102:461-466.
95. Salas A.P., Zhu L., Sanchez C., Brana A.F., Rohr J., Mendez C., Salas J.A. Mol. Microbiol. 2005, 58:17-27.
96. Gaisser S., Reather J., Wirtz G., Kellenberger L., Staunton J., Leadlay P.F. Mol. Microbiol. 2000, 36:391-401.
97. Doumith M., Legrand R., Lang C., Salas J.A., Raynal M.C. Mol. Microbiol. 1999, 34:1039-1048.
98. Wohlert S.-E., Lomovskaya N., Kulowski K., Fonstein L., Occi J.L., Gewain K.M., MacNeil D.J., Hutchinson C.R. Chem. Biol. 2001, 8:681-700.
99. Yang J., Fu X., Jia Q., Shen J., Biggins J.B., Jiang J.Q., Zhao J.J., Schmidt J.J., Wang P.G., Thorson J.S. Org. Lett. 2003, 5:2223-2226.
100. Hoffmeister D., Yang J., Liu L., Thorson J.S. Proc. Natl. Acad. Sci. USA 2003, 100:13184-13189.
101. Yang J., Liu L., Thorson J.S. Chem. Biochem. 2004, 5:992-996.
102. Yang J., Fu X., Liao J., Liu L., Thorson J.S. Chem. Biol. 2005, 12:657-664.
103. Thorson J.S., Barton W.A., Hoffmeister D., Albermann C., Nikolov D.B. Chem. Biochem. 2004, 5:16-25.
104. Barton W.A., Lesniak J., Biggins J.B., Jeffrey P.D., Jiang J.Q., Rajashankar K.R., Thorson J.S., Nikolov D.B. Nat. Struct. Biol. 2001, 8:545-551.
105. Barton W.A., Biggins J.B., Jiang J.Q., Thorson J.S., Nikolov D.B. Proc. Natl. Acad. Sci. USA 2002, 99:13397-13402.
106. Fu X., Albermann C., Jiang J.Q., Liao J.C., Zhang C.S., Thorson J.S. Nat. Biotechnol. 2003, 21:1467-1469.
107. Fu X., Albermann C., Zhang C.S., Thorson J.S. Org. Lett. 2005, 7:1513-1515.
108. Albermann C., Soriano A., Jiang J.Q., Vollmer H., Biggins J.B., Barton W.A., Lesniak J., Nikolov D.B., Thorson J.S. Org. Lett. 2003, 5:933-936.
109. Peri F., Dumy P., Mutter M. Tetrahedron 1998, 54:12269-12278.
110. Peri F., Jimenez-Barbero J., Garcia-Aparicio V., Tvaroska I., Nicotra F. Eur. J. Chem. 2004, 10:1433-1444.
111. Langenhan J.M., Peters N.R., Guzei I.A., Hoffmann F.M., Thorson J.S. Proc. Natl. Acad. Sci. USA 2005, 102:12305-12310.