engleski

Synthesis of peptidoglycan monomer conjugate with monosaccharides

As the component of cell membrane, glycoproteins are an intracellular recognition determining factor. They have multiple roles in biological systems. They participate in the control of cell growth, act as enzymes or hormones and they are responsible for specific immunoreactions1. Isolation or synthesis of glycopeptides as main parts of glycoproteins as well as their modifications are very important in the field of synthetic organic chemistry. Peptidoglycan monomer (PGM ; (beta-D-GlcNAc-(1→ 4)-MurNAc-L-Ala-D- isoGln-[L-meso-A2pm-( NH2)-D-Ala-D-Ala)]) is the basic repeating glycopeptide unit of a peptidoglycane originating from Brevibacterium divaricatum2. It was shown to be an immunostimulating, anti-tumor and anti-metastatic agent3. The purpose of this work was to synthesize conjugates of PGM and some monosaccharides by using (S)-(+)-methyl-3-hydroxy-2-methylpropionat as a connected chain arm. Since it is known that some cell membranes contain receptors for sugar molecules, the final aim could be to study possible changes and/or enhancement of biological activities of PGM linked to the cell surface by a sugar part of prepared conjugates. 1 H. Kunz, Angew. Chem., Int. Ed. 26 (1987) 294-308. 2 D. Keglević, B. Ladišić, J. Tomašić, Z. Valinger and R. Naumski, Biochim. Biophys. Acta 585 (1987) 273- 281. 3 J. Tomašić and I. Hršak in ˝Surface Structures of Microorganisms and Their Interactions with the Mammalian Host˝, E. Schrinner, M. H. Richmond, G. Seibert, U. Schwarz Eds., VCH Publishers, Meinheim, Germany (1988) 113-121.

glycoconjugates ; peptidoglycane monomer ; manose

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