Glycopeptide derivatives

Work with Glycopeptides Derived from Glycophorin A, and with Some Related... 

Although various modifications of the Koenigs-Knorr procedure were used by these workers, the best overall yields of the O-deacetylated glycopeptide derivatives were only 5 to 10%. 

Garg and Jeanloz85,129 131 made extensive use of this procedure in order to obtain L-serine-containing mono-, di-, and tri-glycopeptide derivatives of 2-amino-2-deoxy-D-glucose. Thus, treatment of 6 with the... 

Likewise, the galactosylation of O-glycopeptide derivatives 189-191 to give O-lactosamine - L-serine derivatives (192-194) using (1 - 4)-/ -d-... 

George, S. K. Schwientek, T Holm, B. Reis, C. A. Clausen, H. Kihlberg, J. Chemoenzymatic Synthesis of Sialylated Glycopeptides Derived from Mucins and T-Cell Stimulating Peptides. J. Am. Chem. Soc. 2001, 123, 11117-11125. 

Brand Name(s) Lyphocin, Vancocin, Vancocin HCl, Vancocin HCl Pulvules Cfiemical Class Tricyclic glycopeptide derivative... 

W. Kosch, J. Marz, and H. Kunz, Synthesis of glycopeptide derivatives of peptide T on a solid-phase using an allylic linkage. React. Polym. 22 181 (1994). 

The bleomycins (Fig. 12.6) are a family of glycopeptide-derived antibiotics which are used in the treatment of various tumors. They bind iron in the blood and form an active hypervalent oxo-iron species. The two-dimensional structure is well known but no crystal structures of bleomycin or its metal complexes have been reported. The MM2 force field was modified and extended by modeling of the crystal structures of the cobalt complexes of two bleomycin analogues in order to develop a force field for... 

The carbohydrate content and composition, including the sialic acids of the glycopeptides derived from the Tay-Sachs brain tissues, were found to be the same as those in the normal control although the patterns of gangliosides were markedly different due to excessive accumulation of GM2 in the Tay-Sachs brain (39). 

Malabarba A, Ciabatti R (2001) Glycopeptide derivatives. Curr Med Chem 8 1759-1773... 

Bleomycins (BLMs) (Figure 3a) are a family of glycopeptide-derived antibiotics that have the ability to bind and degrade deoxyribonucleic acid (DNA), which... 

George SK, Schwientek T, Holm B, Reis CA, Clausen H, Kihlberg J, Chemoenzymatic synthesis of sialylated glycopeptides derived from mucins and T-cell stimulating peptides, J. Am. Chem. Soc., 123(45) 11117-25, 2001. 

Modification ofAA4 and AA5 The phenolic group of " Hpg serves as the carbohydrate attachment site, and in semisynthetic approaches, this group has been deriva-tized by protecting groups. Besides these modifications, other glycopeptide derivatives do not exist. This is similarly the case for Hpg, where some naturally occuring derivatives are known, which are chlorinated in the o-position of the... 

The originally nonbiased modifications of glycopeptide molecules used in SAR studies together with the knowledge on the mode of action, stimulated researchers to develop more rational and sophisticated approaches and concepts to raise antibiotic activity of glycopeptide derivatives also against glycopeptide-resistant bacterial strains. A selection of these approaches is discussed in the subsequent sections. 

The bleomycins (BLMs), such as BLM A2, B2, and AS, are a family of antitumor glycopeptide-derived antibiotics isolated from Streptomyces verticillus <2003B9731, 2002JBC2311>. 

Tallysomycins A and B, first isolated from fermentation broths of Streptoalloteichus hindustanus, are glycopeptide-derived antitumor antibiotics structurally related to the bleomycins <20010L2811>. 

Broddefalk, J, Backlund, J, Almqvist, E, Johansson, M, Holmdahl, R, Kihlberg, J, T cells recognize a glycopeptide derived from type II collagen in a model for rheumatoid arthritis, J. Am. Chem. Soc., 120, 7676-7683, 1998. 

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