ABSTRACT
A large number of novel synthetic compounds representing smaller parts of original peptidoglycan molecules have been synthesized and found to possess versatile biological activity, particularly immunomodulating properties. A series of compounds containing the adamantyl residues coupled to peptides and glycopeptides characteristic for bacterial peptidoglycan was described. The new adamantylpeptides and adamantylglycopeptides were prepared starting from N-protected racemic adamantylglycine and dipeptide L-Ala-D-isoglutamine. The adamantyl glycopeptides were obtained by coupling the adamantyltripeptides with alpha-D-mannose moiety through spacer molecule of fixed chirality. Since the starting material was D,L-(adamantyl-glycine) the condensation products with the dipeptide were mixtures of diastereoisomers. The obtained diastereoisomers were separated, characterized, and tested for immunostimulating activity. An HPLC method for purity testing was developed and adapted for the particular compounds.
Subject(s)
Adamantane/chemistry , Glycopeptides/chemistry , Peptides/chemistry , Peptidoglycan/chemistry , Amino Acids , Animals , Antibody Specificity , Chromatography, High Pressure Liquid , Enzyme-Linked Immunosorbent Assay , Female , Fluorenes , Glycopeptides/chemical synthesis , Glycopeptides/immunology , Immunoglobulin G/blood , Immunoglobulin G/immunology , Mannose/chemistry , Mice , Peptides/chemical synthesis , Peptides/immunology , Peptidoglycan/immunologyABSTRACT
The synthesis of racemic and enantiomerically pure N-p-methylbenzyl-3- and N-p-chlorobenzylbenzamidoquinuclidinium bromides (6-8 and 9-11, respectively) is described. These compounds were prepared from racemic or enantiomerically pure 3-benzamidoquinuclidines 3-5 using the appropriate quaternization reagents: p-methyl- benzyl bromide (1) and p-chlorobenzyl bromide (2).
