Immunologically active dipeptidyl saccharides and methods of preparation

A composition comprising a vaccine for human or animal administration and an antibacterially effective amount of a 2-amino-2-deoxy-glycose compound of the general structural formula:

• ##STR11## provided said glycose is not 2-amino-2-deoxy-D-glucose, wherein R.sub.1 is hydrogen, alkyl of 1 to 7 carbon atoms optionally substituted by hydroxy, mercapto, alkoxy of 1 to 3 carbon atoms, alkyl mercapto of 1 to 3 carbon atoms, hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms, halogen, carboxyl, carboxyl esterified by an alcohol of 1 to 3 carbon atoms, or amidated carboxyl,
• phenyl, benzyl, each optionally substituted by alkyl of 1 to 3 carbon atoms, lower alkyldioxy, amino, trifluoromethyl, hydroxy, mercapto, hydroxy or mercapto etherified by alkyl of 1 to 3 carbon atoms, or hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms;
• R.sub.2 is alkyl of 1 to 7 carbon atoms optionally substituted by hydroxy, mercapto, alkoxy of 1 to 3 carbon atoms, alkyl mercapto of 1 to 3 carbon atoms, hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms, halogen, carboxyl, carboxyl esterified by an alcohol of 1 to 3 carbon atoms, or amidated carboxyl,
• phenyl, optionally substituted by alkyl of 1 to 3 carbon atoms, lower alkyldioxy, amino, trifluoromethyl, hydroxy, mercapto, hydroxy or mercapto etherified by alkyl of 1 to 3 carbon atoms, or hydroxy or mercapto esterified by an acid of 1 to 4 carbon atoms;
• R.sub.3 is H or alkyl of 1 to 10 carbon atoms;
• R.sub.4 and R.sub.5 are same or different and are
• hydrogen, alkanoyl of 2 to 21 carbon atoms,
• benzoyl, naphthoyl-1 or naphthoyl-2 each optionally substituted by halogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, trifluoromethyl, hydroxy or alkanoyloxy of 1 to 3 carbons,
• an alkanesulfonic acid of 1 to 7 carbon atoms, or a phenylsulfonic acid optionally substituted by alkyl of 1 to 3 carbon atoms,
• carbamoyl, alkyl carbamoyl of 1 to 3 carbon atoms, phenylcarbamoyl or napththylcarbamoyl;
• R.sub.6 is H or R.sub.6 -R.sub.7 together is --CH.sub.2 --CH.sub.2 --CH.sub.2 --;
• R.sub.7 is H, alkyl of 1 to 7 carbon atoms, hydroxymethyl,
• mercaptomethyl, benzyl;
• or substituted benzyl wherein the substituents are the same as defined for R.sub.1 ;
• R.sub.8 and R.sub.9 each is carboxyl, esterified carboxyl of 1 to 7 carbon atoms, amidated carboxyl, or mono- or dialkyl amidated carboxyl wherein the alkyl group has 1 to 3 carbon atoms;
• provided that when R.sub.3 is lower alkyl, the stereochemistry at asymmetric center I can be either D or L, when R.sub.7 is not H, the stereochemistry at asymmetric center II is either L or D, and the stereochemistry at asymmetric center III is D.