Bacteria vancomycin-resistant

Gaspar-Marques,C. Rijo,P. Sim5es, M. F. Duarte,M. A. Rodriguez, B. Abietanesfrom Plectranthus grandidentatus and P. hereroensis against methicillin- and vancomycin-resistant bacteria. Phytomedicine 2006, 13, 267-271. 

More recently, eveminomycins have also been introduced as antibiotics that inhibit the synthesis of bacterial cell walls. They show excellent activity against fluoroquinolone-resistant bacteria and all gram-positive vancomycin-resistant bacteria (Lin et al., 2000). 

Nicolaou KC, Cho SY, Hughes R, Winssinger N, Smethurst C, Labischinski H, Endermann R, Solid and solution phase synthesis of vancomycin and vanxcomycin analogues with activity against vancomycin-resistant bacteria, Chemistry, 7(17) 3798-823, 2001. 

S.2.2 Glycopeptides and Glycopeptide-Based Approaches with Antibiotic Activity Against Vancomycin-Resistant Bacteria... 

Scheme 2-12. Approaches for the design of glycopeptide-related molecules with also activity against vancomycin-resistant bacteria, (a) Chlorobiphenylbenzyl derivatives with activity against (b) D-Ala-D-Lac small molecule cleavers (c) Synthetic receptors from a...

The story of the involvement of glycosyl moieties in vancomycin activity is probably one of the most illustrative and also very topical as glycosyl derivatives of vancomycin quite recently proved to be very effective against multiply resistant (even vancomycin-resistant) bacteria. 

Nicolaou, K. C., Hughes, R., Cho, S. Y., Winssinger, N., Labischinski, H., Endermann, R. Synthesis and biological evaluation of vancomycin dimers with potent activity against vancomycin-resistant bacteria target-accelerated combinatorial synthesis. Chem. Eur. J. 2001, 7, 3824-3843. 

Some bacteria become resistant to vancomycin, and thrive in the presence of the antibiotic. The developing cell wall of vancomycin-resistant bacteria has a slightly different composition that the drug molecule does not recognize. Specialized resistance genes provide the resistant bacteria with the ability to reprogram the composition of the cell wall. 

A number of combinatorial-based syntheses have been reported. Andrus et al. prepared a solution-phase indexed combinatorial library of nonnatural polyenes such as 291 for multidrug resistance reversal.298 This library was formed by modification of R and R. Ellman and co-workers reported a combinatorial library of synthetic receptors targeting vancomycin-resistant bacteria,209 and Paterson et al. prepared polyketide-type libraries by iterative asymmetric aldol reactions on solid support.2l0 Rieser et al. used combinatorial liquid-phase synthesis to prepare [1,4]-oxazepine-7-ones by the Baylis-Hillman reaction (see sec. 9.7.B).2H Schreiber and co-workers reported the synthesis and evaluation of a library of polycyclic small molecules for use in chemical genetic assays.2 2 Bauer et al. reported a library of N-substituted 2-pyrazoline compounds... 

Only very recently, despite decades of intensive use, have some vancomycin-resistant bacteria emerged... 

Wohlrab, A., Lamer, R. and VanNieuwenhze, M.S. (2007) Total synthesis of plusbacin A3 a depsipeptide antibiotic active against vancomycin-resistant bacteria. Journal of the American Chemical Society, 129, 4175-4177. 

Xie J, Pierce JG, James RC, Okano A, Boger DL (2011) A redesigned vancomycin engineered for dual D-Ala-D-Ala and D-Ala-D-Lac binding exhibits potent antimiciDbial activity against vancomycin-resistant bacteria. J Am Chem Soc 133 13946-13949... 

Xu, R. et al., Combinatorial library approach for the identification of synthetic receptors targeting vancomycin-resistant bacteria, J. Am. Chem. Soc., 121, 4898, 1999. 

FIGURE 11.28 Vancomycin-based receptor bbraries. (From Xu, R. et al., Combinatorial bbrary approach for the identification of synthetic receptors targeting vancomycin-resistant bacteria, J. Am. Chem. Soc., 121, 4898, 1999 Kateri, A.A. et al.. Identification of potent and broad-spectrum antibiotics from SAR studies of a synthetic vancomycin analog, Bioorg. Med. Chem. Lett., 13, 1683, 2003.)... 

Nicolaou, K.C. et al.. Solid- and soluhon-phase synthesis of vancomycin and vancomycin analogs with achvity against vancomycin-resistant bacteria, Chem Eur. J., 7, 3798, 2001. 

Until relatively recently, the last discovery of a new class of antibiotics was in the 1970s, so drug reastance became an increasingly important problem in medicinal chemistry. Vancomycin had been the antibiotic of last resort because there were no reported cases of vancomycin-resistant bacteria until 1989, when more and more bacteria became resistant. 

Paris, France) for the treatment of vancomycin-resistant bacteria. A recent synthetic approach by Moreau and Campagne highlighted the intermolecular palladium-catalyzed crosscoupling strategy using vinyl iodide 434 and thiol 435 in an efficient synthesis of the nine-membered core 437 of griseoviridin,whereas the previous total synthesis by Meyers et al. employed the thioether formation 440 by an enolate chemistry of (3-keto ester 438 with a 5-phthalimdo compound 439 to introduce the sulfur moiety (Scheme 46.49). ... 

---