Disaccharide dipeptides

The synthesis of the disaccharide dipeptide (76), an analogue of (75), has been described recently (20). The tetra-O-benzoyl-a-D-glucopyranosyl bromide was condensed by a Konigs-Knorr reaction with benzyl-2-acet-amido-6-0-benzoyl-3-0-(D-l-carboxyethyl)-2-deoxy-a-D-glucopyrano-... 

The disaccharide dipeptide (7) was synthesized by initial condensation using... 

C27H45N5O16 695.676 Repeating disaccharide-dipeptide unit of bacterial cell wall peptidoglycan. Exhibits immunoadjuvant activity. Hygroscopic powder. Mp 170-178° (dec.), [ajo -<-0.6 (c, 1 in H2O). 

Worth, L.L. et al., ImmTher, a lipophilic disaccharide derivative of muramyl dipeptide, up-regulates specific monocyte cytokine genes and activates monocyte- mediated tumoricidal activity, Cancer Immunol Immunother., 48, 312, 1999. 

Fractionation of mycobacteria resulted in the identification of two cellular immunostimulatory components, trehalose dimycolate (TDM) and muramyl dipeptides (MDP). Both are normally found in association with the mycobacterial cell wall. TDM is composed of a molecule of trehalose (a disaccharide consisting of two molecules of a-D-glucose linked via an a 1-1 glycosidic bond), linked to two molecules of mycolic acid (a long-chain aliphatic hydrocarbon-based acid) found almost exclusively in association with mycobacteria. TDM, while retaining its adjuvanticity, is relatively non-toxic. 

C -(2-Acetamido-2-deoxy 3-D-glucosyl)-(l 4)-iV-acetyl muramoyl-L-alanyl-D-isoglutamine (31), the dipeptide derivative of the disaccharide isolated from lysozyme digests of bacterial cell walls, has been prepared in a fourteen-step sequence from 2-acetamido-2-deoxy-D-glucose. The dipeptide disaccharide derivative (32) isolated from lysostaphin endo-l3-D-2-acetamido-2-deoxy-glucan-ase digests of cell walls has also been synthesized (Scheme 5). ... 

Figure 1 Comparison of relaxed maps made with Charmm software and plotted at contour intervals of 1 kcal/mole A) Alanine dipeptide. B) Disaccharide, Gal )9-(l-- 3)-Gal 0-...

The glycosylating disaccharide derivative (30) was of limited value when used with the diserine compound (3D. A better method for making the disubstituted dipeptide involved condensation of two disaccharide serine derivatives. Two deoxy derivatives of... 

---