Vancomycin dimer

Loll, P.J. et ah. Simultaneous recognition of a carboxylate-containing ligand and an intramolecular surrogate ligand in the crystal structure of an asymmetric vancomycin dimer, J. Am. Chem. Soc., 119, 1516, 1997. 

Figure 1.12 Target-accelerated synthesis of vancomycin dimers via olefin metathesis (n = 2 or 4).

Scheme 2.9 DCLs of vancomycin dimers using crossmetathesis and disulfide bond formation.

Nicolaou KC, Hughes R, Cho SY, Winssinger N, Labischinski H, Endermann R, Synthesis and biological evaluation of vancomycin dimers with potent activity target accelerated combinatorial synthesis, Chemistry, 7(17) 3824M-3, 2001. 

Jain, R.K., Trias, J., and Ellman, J.A., D-Ala-D-Lac binding is not required for the high activity of vancomycin dimers against vancomycin resistant Enterococci, J. Am. Chem. Soc., 125, 8740, 2003 and references cited therein. 

FIGURE 11.30 Target-accelerated combinatorial synthesis (TAGS) of vancomycin dimers. (From Nicolaou, K.C. et al.. Synthesis and biological evaluation of vancomycin dimmers with potent activity against vancomycin-resistant bacteria target-accelerated combinatorial synthesis, Chem. Eur. J., 7, 3824, 2001.)... 

Ac2-L-Lys-D-Ala-D-Ala metathesis/thiol-disulfide exchange 36 vancomycin dimers [66]... 

Figure 5.29 Vancomycin dimers targeting cell surface peptides. X—X = S—S, CH=CH.

Abstract Medical studies established that vancomycin and other related macro-cyclic antibiotics have an enhanced antimicrobial activity when they are associated as dimers. The carbohydrate units attached to the vancomycin basket have an essential role in the dimerization reaction. Covalently synthesized dimers were found active against vancomycin-resistant bacterial strains. A great similarity between antibiotic potential and enantioselectivity was established. A covalent vancomycin dimer was studied in capillary electrophoresis producing excellent chiral separation of dansyl amino acids. Balhimycin is a macrocyclic glycopeptide stmcturally similar to vancomycin. The small differences are, however, responsible for drastic differences in enantioselectivity in the same experimental conditions. Contributions from studies examining vancomycin s mechanism for antimicrobial activity have substantially aided our understanding of its mechanism in chiral recognition. 

Table 1 Resolution of dansyl-D,L -valine versus pH obtained by CE separation with vancomycin dimer chiral selector...

Table 2 Enantiomeric resolutions, migration times, and apparent mobilities of racemates using a covalently bound vancomycin dimer as chiral resolving agent...

Jourdan E et al (2003) Use of an amino stationary phase to study the vancomycin dimerization dependence on solute enantioselectivity. J Liq Chromatogr Relat Tech 26 1027—1039... 

Sundram U, Griffin J, Nicas T (1996) Novel vancomycin dimers with activity against vancomycin-resistant enterococci. 1 Am Chem Soc 118 13107-13108... 

Slama I et al (2002) Vancomycin dimerization and chiral recognition studied by high-performance hquid chromatography. Anal Chem 74 5205-5211... 

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