Engineering a methymycin/pikromycin-calicheamicin hybrid: Construction of two new macrolides carrying a designed sugar moiety [6]

Journal of the American Chemical Society

Volumn 121, Issue 42, 1999, Pages 9881-9882

  Zhao, Lishan ^a   Ahlert, Joachim ^c   Xue, Yongquan ^b   Thorson, Jon S ^c   Sherman, David H ^b   Liu, Hung Wen ^a  

^a University of Minnesota   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CALICHEAMICIN; DNA; MACROLIDE; METHYMYCIN; PIKROMYCIN; UNCLASSIFIED DRUG;

BIOSYNTHESIS; DNA BINDING; GENE CLUSTER; GENETIC MANIPULATION; GLYCOSYLATION; LETTER; NONHUMAN; STREPTOMYCES;

EID: 0033610483     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992810k     Document Type: Letter

References (36)

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9. Targeted deletion/disruption of the desVI, desV, or desI genes in the methymycin/pikromycin cluster has led to the production of methymycin/ pikromycin derivatives carrying, instead of desosamine, 3-acetamido-3,4,6-trideoxyglucose, 4,6-dideoxyglucose, or 6-deoxyglucose (quinovose) as the appended sugar by the respective mutants [(a) Zhao, L.; Sherman, D. H.; Liu, H.-w. J. Am. Chem. Soc. 1998, 120, 10256-10257. (b) Zhao, L.; Que, N. L. S.; Xue, Y.; Sherman, D. H.; Liu, H.-w. J. Am. Chem. Soc. 1998, 120, 12159-12160. (c) Borisova, S. A.; Zhao, L.; Sherman, D. H.; Liu, H.-w. Org. Lett. 1999, 1, 133-136].
10. Targeted deletion/disruption of the desVI, desV, or desI genes in the methymycin/pikromycin cluster has led to the production of methymycin/ pikromycin derivatives carrying, instead of desosamine, 3-acetamido-3,4,6-trideoxyglucose, 4,6-dideoxyglucose, or 6-deoxyglucose (quinovose) as the appended sugar by the respective mutants [(a) Zhao, L.; Sherman, D. H.; Liu, H.-w. J. Am. Chem. Soc. 1998, 120, 10256-10257. (b) Zhao, L.; Que, N. L. S.; Xue, Y.; Sherman, D. H.; Liu, H.-w. J. Am. Chem. Soc. 1998, 120, 12159-12160. (c) Borisova, S. A.; Zhao, L.; Sherman, D. H.; Liu, H.-w. Org. Lett. 1999, 1, 133-136].
11. Targeted deletion/disruption of the desVI, desV, or desI genes in the methymycin/pikromycin cluster has led to the production of methymycin/ pikromycin derivatives carrying, instead of desosamine, 3-acetamido-3,4,6-trideoxyglucose, 4,6-dideoxyglucose, or 6-deoxyglucose (quinovose) as the appended sugar by the respective mutants [(a) Zhao, L.; Sherman, D. H.; Liu, H.-w. J. Am. Chem. Soc. 1998, 120, 10256-10257. (b) Zhao, L.; Que, N. L. S.; Xue, Y.; Sherman, D. H.; Liu, H.-w. J. Am. Chem. Soc. 1998, 120, 12159-12160. (c) Borisova, S. A.; Zhao, L.; Sherman, D. H.; Liu, H.-w. Org. Lett. 1999, 1, 133-136].
12. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
13. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
14. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
15. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
16. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
17. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
18. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
19. A similar relaxed specificity toward sugar substrates has also been reported for the glycosyltransferases in the biosynthesis of a few other secondary metabolites (see the following examples: Weber, J. M.; Leung, J. O.; Swanson, S. J.; Idler, K. B.; McAlpine, J. B. Science 1991, 252, 114-117. Decker, H.; Haag, S.; Udvarnoki, G.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1107-1110. Sasaki, J.; Mizoue, K.; Morimoto, S.; Omura, S. J. Antibiot. 1996, 49, 1110-1118. Solenberg, P. J.; Matsushima, P.; Stack, D. R.; Wilkie, S. C.; Thompson, R. C.; Baltz, R. H. Chem. Biol. 1997, 4, 195-202. 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. Nature Biotechnol. 1998, 16, 69-74. Salah-Bey, K.; Doumith, M.; Michel, J.-M.; Haydock, S.; Cortes, J.; Leadlay, P. F.; Raynal, M.-C. Mol. Gen. Genet. 1998, 257, 542-553. Gaisser, S.; Bohm, G. A.; Doumith, M.; Raynal, M.-C.; Dhillon, N.; Cortés, J.; Leadlay, P. F. Mol. Gen. Genet. 1998, 258, 78-88. 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).
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