C-LINKED NEOGLYCOPEPTIDES, THEIR COMBINATORIAL SYNTHESIS AND USE

摘要

Provided are neoglycopeptides comprising a peptide of 1 to 15 amino acid residues in which at least one amino group or internal amide nitrogen bears a saccharide either attached directly or via a group of the formula (CH2CH2)G<1> and/or (COCH2)G<2> wherein G<1> and G<2> are independently selected from the saccharides, (the hydroxyl groups of which saccharides may optionally be protected), and wherein G<1> and G<2> are respectively linked to the (CH2CH2) and (COCH2) moieties via a carbon atom. Also provided is a solid-phase method for preparing a neoglycopeptide according to the invention, comprising assembling a string of amino acids immobilized on a resin by solid-phase synthetic methods, wherein during assembly at least one glyco-linking reaction is carried out, comprising reacting a terminal amino group with (A) a compound capable of forming a group of formula -NH(CXCH2)G<2> upon reacting with a terminal amino group [wherein G<2> is selected from saccharides, the hydroxyl groups of which are protected, and X represents two hydrogen atoms or an oxygen atom], or (B) a compound capable of forming a group of formula -NHG<2> upon reacting with a terminal amino group [wherein G<2> is defined as above].