Biomimetic synthesis and structural refinement of the macrocyclic dimer aminoglycoside 66-40C - The remarkably selective self-condensation of a putative aldehyde intermediate in the submerged culture medium producing sisomicin

Chemical Communications

Volumn 46, Issue 12, 2010, Pages 2013-2015

  Hanessian, Stephen ^a   Maianti, Juan Pablo ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; DIMER; MACROCYCLIC COMPOUND; SISOMICIN;

ARTICLE; BIOMIMETICS; CULTURE MEDIUM; DIMERIZATION; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYPOTHESIS; MICROMONOSPORA; NONHUMAN; POLYMERIZATION;

EID: 77949406714     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b925668g     Document Type: Article

References (19)

1. M. J. Weinstein, J. A. Marquez, R. T. Testa, G. H. Wagman, E. M. Oden and J. A. Waitz, J. Antibiot., 1970, 23, 551;
2. G. H. Wagman and M. J. Weinstein, Annu. Rev. Microbiol., 1976, 9, 537.
3. D. P. Arya, Aminoglycoside Antibiotics: From Chemical Biology to Drug Discovery, Wiley, Hoboken, New Jersey, 2007;
4. C. Walsh, Antibiotics: Actions, Origins, Resistance, ASM Press, Washington, DC, 2003.
5. D. H. Davies, A. K. Mallams, J. McGlotten, J. B. Morton and R. W. Tkach, J. Chem. Soc., Perkin Trans. 1, 1977, 1407;
6. D. H. Davies, D. Greeves, A. K. Mallams, J. B. Morton and R. W. Tkach, J. Chem. Soc., Perkin Trans. 1, 1975, 814.
7. D. H. Davies, A. K. Mallams, M. Counelis, D. Loebenberg, E. L. Moss Jr. and J. A. Waitz, J. Med. Chem., 1978, 21, 189.
8. R. T. Testa and B. C. Tilley, J. Antibiot., 1976, 29, 140;
9. E. J. Hessler, H. K. Jahnke, J. H. Robertson, K. Tsuji, K. J. Rinehart Jr. and W. T. Shier, J. Antibiot., 1970, 23, 464;
10. G. H. Wagman and J. Weinstein, Journal of Chromatography Library, Antibiotics-Isolation, Separation, Purification, Elsevier, Amsterdam, 1978, vol. 15.
11. S. Hanessian, J. Szychowski and J. P. Maianti, Org. Lett., 2009, 11, 429. DHP = 3,4-dihydro-[2H]-pyran.
12. H. Paulsen, R. Jansen and P. Stadler, US pat., 4 195 173, 1980;
13. H. Paulsen and R. Jansen, Carbohydr. Res., 1981, 92, 305.
14. J. R. Cox and E. H. Serpersu, Biochemistry, 1997, 36, 2353;
15. R. S. Kane, P. T. Glink, R. G. Chapman, J. C. McDonald, P. K. Jensen, H. Gao, L. Pasa-Tolić, R. D. Smith and G. M. Whitesides, Anal. Chem., 2001, 73, 4028.
16. 3 matching atoms of rings A and B of paromomycin. Fig. 3 image produced in PyMol.
17. Q. Vicens and E. Westhof, Structure (London), 2001, 9, 647.
18. For review see: B. François, R. J. Russell, J. B. Murray, F. Aboul-ela, B. Masquida, Q. Vicens and E. Westhof, Nucleic Acids Res., 2005, 33, 5677.
19. D. H. Fong and A. M. Berghuis, EMBO J., 2002, 21, 2323.