Glycopeptide antibiotics structure

Vancomycin is a glycopeptide antibiotic structure, used in the prophylaxis and treatment of infections caused by Gram-positive bacteria. 

Groves F, Seaile MS, Mackay JP, Williams DH. The stiuctuie df an asymmetric dimer relevant to the mode of action of glycopeptide antibiotics. Structure 1994 2 747-754. 

Lee, J.-G., Sagui, C., and Roland, C., Quantum simulations of the structure and binding of glycopeptide antibiotic aglycones to cell wall analogues, J. Phys. Chem. B, 109, 20588, 2005. 

Vancomycin Vancomycin (32.7.2) was isolated in 1956 from the products of the functional activity of actinomycetes Streptomyces orientalis (cnrrently Nocardia orientalis). Based on its chemical structure and contents, vancomycin is classified as a glycopeptide antibiotic. Its molecular mass is significantly more than practically any other used antibiotics [325-330]. 

Macrolactamization has limitations. All macrolactamization methods studied to date are ineffective at forming 14-membered cycloisodityrosines of the type found in deoxy-bouvardin (2) and RA-VII (3).[1° In addition, macrolactamization was not successful at preparing 16-membered rings that are structurally similar to cycloisodityrosines, such as the type found in the vancomycin family of glycopeptide antibiotics.[11 12 ... 

Another agent which has found application in tumor imaging is luIn-bleomycin.505 The bleomycins are naturally occurring water-soluble copper-containing glycopeptide antibiotics having the generic structure (42), in which R may be a variety of substituent as shown in Table 23.723... 

Wolter F, Schoof S, Sussmuth R (2007) Synopsis of structural, biosynthetic, and chemical aspects of glycopeptide antibiotics. Top Curr Chem 267 143-185... 

Malabarba A, Nicas TI, Thompson RC (1997) Structural modifications of glycopeptide antibiotics. Med Res Rev 17 69-137... 

Structural Formula Complex of glycopeptide antibiotics produced by... 

Figure 1.3 Chemical structures of glycopeptides antibiotics vancomycin (1) [1], eremomycin (2) [15a], ristocetin A (3) [15b], and teicoplanin (4) [15c],...

Other complex glycopeptide antibiotics (90-96) produced by S. virginiae [83] contain galactose in their chemical structure. 

Scheme 2-1. Structures of important vancomycin-type glycopeptide antibiotics.

Remarkably, it took almost 25 years to unravel the structure of glycopeptide antibiotics. The reasons are based on the highly complex structure of glycopeptides and the limited power of analytical methods, especially of nuclear magnetic resonance (NMR) methods, by that time. With the progress in the development of NMR... 

Scheme 2-2. Structures of the five naturally occurring glycopeptide antibiotic subtypes.

STRUCTURAL MODIFICATIONS OF GLYCOPEPTIDE ANTIBIOTICS AND STRUCTURE ACTIVITY RELATIONSHIP (SAR) STUDIES... 

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