Biosynthesis of desosamine: Construction of a new macrolide carrying a genetically designed sugar moiety

Organic Letters

Volumn 1, Issue 1, 1999, Pages 133-136

  Borisova, Svetlana A ^a   Zhao, Lishan ^a   Sherman, David H ^b   Liu, Hung Wen ^a  

^a University of Minnesota   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR; ANTIINFECTIVE AGENT; CARBOHYDRATE; DESOSAMINE; MACROLIDE; METHYMYCIN; NEOMETHYMYCIN;

ARTICLE; BIOSYNTHESIS; CHEMISTRY; GENETICS; METABOLISM; MUTATION; PROTEIN CONFORMATION; STREPTOMYCES;

AMINO SUGARS; ANTI-BACTERIAL AGENTS; CARBOHYDRATES; MACROLIDES; MUTATION; PROTEIN CONFORMATION; STREPTOMYCES;

EID: 0033565017     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9906007     Document Type: Article

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23. 1H NMR spectra with literature data for 12 (Lambalot, R. H.; Cane, D. E. J. Antibiot. 1992, 45, 1981), (Oikawa, Y.; Tanaka, T.; Yonemitsu, O. Tetrahedron Lett. 1986, 27, 3647 and Ditrich, K. Lie bigs Ann. Chem. 1990, 8, 789) and 14 (Inanaga, J.; Kawanami, Y.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1986, 59, 1521).
24. 1H NMR spectra with literature data for 12 (Lambalot, R. H.; Cane, D. E. J. Antibiot. 1992, 45, 1981), (Oikawa, Y.; Tanaka, T.; Yonemitsu, O. Tetrahedron Lett. 1986, 27, 3647 and Ditrich, K. Lie bigs Ann. Chem. 1990, 8, 789) and 14 (Inanaga, J.; Kawanami, Y.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1986, 59, 1521).
25. 1H NMR spectra with literature data for 12 (Lambalot, R. H.; Cane, D. E. J. Antibiot. 1992, 45, 1981), (Oikawa, Y.; Tanaka, T.; Yonemitsu, O. Tetrahedron Lett. 1986, 27, 3647 and Ditrich, K. Lie bigs Ann. Chem. 1990, 8, 789) and 14 (Inanaga, J.; Kawanami, Y.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1986, 59, 1521).
26. + 443.2644, found 443.2661.
27. 7b,c pathways.
28. 7b,c pathways.
29. 7b,c pathways.
30. This enzyme can accept both 12-and 14-membered-ring macrolide substrates and is active on both C-10 and C-12 of the 12-membered ring (Xue, Y.; Wilson, D.; Zhao, L.; Liu, H.-w.; Sherman, D. H. Chem. Biol. 1998, 5, 661).