Multi-valent polymer of vancomycin: Enhanced antibacterial activity against VRE

Chemical Communications

Volumn , Issue 15, 1999, Pages 1361-1362

  Arimoto, Hirokazu ^a,b,c   Nishimura, Kazuya ^a,b,c   Kinumi, Tomoya ^a,b,c   Hayakawa, Ichiro ^a,b,c   Uemura, Daisuke ^a,b,c  

^a SHIZUOKA UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF INFECTIOUS DISEASES   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

POLYPEPTIDE ANTIBIOTIC AGENT; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; ENTEROCOCCUS; STAPHYLOCOCCUS AUREUS;

EID: 0033533176     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903529j     Document Type: Article

References (19)

1. For recent reviews on this field, see D. Niccolai, L. Tarsi and R. J. Thomas, Clicm. Commun., 1997, 2333.
2. See also D. H. Williams and B. Bardsley, Angcw. Client., Int. Ed., 1999, 38, 1173.
3. M. Mammen, S. K. Choi and G. M. Whitesides, Angcw. Clicm., Int. Ed., 1998, 37, 2754.
4. L. L. Kiessling and N. L. Pohl, Cliem. Biol., 1996, 3, 71.
5. For some examples of niultivalent polymers with non-sugar ligands: V. C. Gibson, E. L. Marshall, M. North, D. A. Robson and' P. J. Williams, Client. Commun., 1997, 1095;
6. S. C. G. Biagini, V. C. Gibson, M. R. Giles, E. L. Marshall and M. North, Cliem". Commun., 1997, 1097.
7. D. H. Williams, Nat. Prod. Rep., 1996, 13, 469. In VanA and VanB resistance, pentapeptide terminals are changed from -n-Ala-n-Ala to -DAla-D-Lac, which makes the binding of vancomycin considerably weaker.
8. C. M. Harris, H. Kopecka and T. M. Harris, J. Am. Cliem. Soc., 1983, 105,6915.
9. Vancomycin is also sensitive to acidic and oxidative conditions, see R. Nagarajan and A. A. Schabet, Client. Commun., 1988, 1306;
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11. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Ançcw. Clicm., Int. Ed. Engl., 1995, 34, 2039.
12. For compatibility of metathesis catalysts w ith various functional groups, see review: S. K. Armstrong, J. Clicm. Soc., Pcrkin Trans. I, 1998, 371.
13. See also R. H. Grubbs and S. Chang, Tetrahedron, 1998,54,4413;
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15. R. D. G. Cooper, N. J. Snyder, M. J. Zweifel, M. A. Staszak, S. C. Wilkie, T. I. Nicas, D. L. Müllen, T. F. Butler, M. J. Rodriguez, B. E. Huffand R. C. Thomspon,J. Antibiot., 1996,49, 575;
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17. Monoisotopic mass.
18. D. M. Lynn, S. Kanaoka and R. H. Grubbs, J. Am. Clicm. Soc., 1996, 118,784.
19. We believe that monomer 1 was used as a trifuoroacetic acid salt, since the Chromatographie purification of 1 was done by a TFA-containing solvent system. Thus, the key to the success in the metathesis polymerization may be the ammonium salt formation of two scr-amines in 1, which prevented the deactivation of catalyst.