Immunologically active peptidyl disaccharides and methods of preparation

A 2-amino-2-deoxy-.beta.-D-glucopyranosyl-(1.fwdarw.4)-2-amino-2-deoxy-D-glu cose of the general structural formula:

• ##STR14## wherein R.sub.1 is hydrogen, alkyl (1-7C), substituted alkyl (1-7C) wherein the substituent is hydroxy, mercapto, alkoxy of 1-3 carbons, alkyl mercapto of 1-3 carbons, hydroxy or mercapto esterified by an acid of 1-4 carbon atoms, F, Cl, Br, carboxyl, or carboxyl functionally modified by esterification with an alcohol of 1-3 carbons or by amidation, phenyl, substituted phenyl wherein the substituent is an alkyl group of 1-3 carbons, hydroxy, mercapto, hydroxy or mercapto etherified by an alkyl group of 1-3 carbons, hydroxy or mercapto esterified by an acid of 1-4 carbons, alkyldioxy (1-4C), cycloalkyldioxy (5-7C), amino or trifluoromethyl, benzyl, or substituted benzyl wherein the substituent is an alkyl group of 1-3 carbons, hydroxy, mercapto, hydroxy or mercapto etherified by an alkyl group of 1-3 carbon atoms, hydroxy or mercapto esterified by an acid of 1-4 carbons, alkyldioxy (1-4C), cycloalkyldioxy (5-7C), amino or trifluoromethyl;
• R.sub.2 is alkyl (1-7C), substituted alkyl (1-7C) wherein the substituent is hydroxy, mercapto, alkoxy of 1-3 carbons, alkylmercapto of 1-3 carbons, hydroxy or mercapto esterified by an acid of 1-4 carbon atoms, F, Cl, Br, carboxyl, or carboxyl functionally modified by esterification with an alcohol of 1-3 carbons or by amidation, phenyl, or substituted phenyl wherein the substituent is an alkyl group of 1-3 carbons, hydroxy, mercapto, hydroxy or mercapto etherified by an alkyl group of 1-3 carbon atoms, hydroxy or mercapto esterified by an acid of 1-4 carbons, alkyldioxy (1-4C), cycloalkyldioxy (5-7C), amino or trifluoromethyl and each R.sub.2 may be the same group or a different group;
• R.sub.3 and R'.sub.3 are H or ##STR15## wherein R.sub.8 is H or lower alkyl (1-10C), and provided at least one of R.sub.3 and R'.sub.3 is not H;
• R.sub.9 is H, or R.sub.9 -R.sub.10 together is --CH.sub.2 CH.sub.2 CH.sub.2 --;
• R.sub.10 is H, alkyl (1-7C) hydroxymethyl, mercaptomethyl, benzyl, or substituted benzyl wherein the substituent is an alkyl group of 1-3 carbon atoms, hydroxy, mercapto, hydroxy or mercapto etherified by an alkyl group of 1-3 carbons, hydroxy or mercapto esterified by an acid of 1-4 carbons, alkyldioxy (1-4C), cycloalkyldioxy (5-7C), amino or trifluoromethyl;
• R.sub.11 and R.sub.12 each are independently carboxyl, esterified carboxyl (1-7C), amidated carboxyl, or mono- or di-alkyl (1-7C) amidated carboxyl;
• R.sub.4, R.sub.5 and R'.sub.5 are the same or different and are H, aliphatic or aromatic acyl (2-21C) or substituted acyl (2-21C) wherein the substituent is halogen, alkyl (1-3C), alkoxy (1-3C), trifluoromethyl, hydroxy, alkanoyloxy (1-3C),
• provided when R.sub.8 is loweralkyl, the stereo chemistry at asymmetric center I can be either D or L;
• and when R.sub.10 is not H, the stereochemistry at asymmetric center II is L;
• the stereochemistry at asymmetric center III is D;
• provided further when R.sub.1, R.sub.5, R'.sub.3, R.sub.4, and R'.sub.5 are each H and each R.sub.2 is CH.sub.3, R.sub.3 is not H.sub.3 CCHCOR.sub.13 wherein R.sub.13 is a dipeptide.