Novel glycoconjugates, glycoamino acids, intermediates thereto, and uses thereof

A multi-antigenic glycopeptide comprising a peptidic backbone made up of at least three amino acid residues, wherein one or more of said amino acids are independently:

• wherein each occurrence of A is a carbohydrate determinant having the structure:
• wherein a, b, c, d, e, f, g, h, i, x, y and z are independently 0, 1, 2 or 3, with the proviso that the x, y and z bracketed structures represent pyranose moieties and the sum of b and c is 2, the sum of d and f is 2, and the sum of g and i is 2, and with the proviso that x, y and z are not simultaneously 0;
• wherein R0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group;
• wherein each occurrence of R1, R2, R3, R4, R5, R6, R7, R8 and R9 is independently hydrogen, OH, ORi, NHRi, NHCORi, F, CH2OH, CH2ORi, a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group;
• wherein each occurrence of Ri is independently hydrogen, CHO, COORii, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group or a saccharide moiety having the structure:
• wherein Y and Z are independently NH or O;
• wherein k, l, r, s, t, u, v and w are each independently 0, 1 or 2;
• with the proviso that the v and w bracketed structures represent pyranose moieties and the sum of 1 and k is 2, and the sum of s and u is 2, and with the proviso that v and w are not simultaneously 0;
• wherein R′0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group;
• wherein each occurrence of R10, R11, R12, R13, R14 and R15 is independently hydrogen, OH, ORiii, NHRiii, NHCORiii, F, CH2OH, CH2ORiii, or a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group;
• wherein each occurrence of R16 is hydrogen, COOH, COORii, CONHRii, a substituted or unsubstituted linear or branched chain alkyl or aryl group;
• wherein each occurrence of Riii is hydrogen, CHO, COORiv, or a substituted or unsubstituted linear or branched chain alkyl, acyl, arylalkyl or aryl group;
• and wherein each occurrence of Rii and Riv are each independently H, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group;
• wherein each occurrence of n is independently 0-8, whereby, if for each occurrence of n, n=0, at least one occurrence of A has a different structure from other occurrences of A;
• and
• at least one occurrence of A is a carbohydrate determinant having the structure:
• wherein each occurrence of R′ is independently hydrogen or a protecting group;
• and wherein R″ is hydrogen or a nitrogen protecting group.

The glycopeptide of claim 1, wherein said glycopeptide is a construct having the structure:

• wherein the linker is either a free carboxylic acid, (carboxamido)alkyl carboxamide, MBS, primary carboxamide, mono- or dialkyl carboxamide, mono- or diarylcarboxamide, linear or branched chain (carboxy)alkyl carboxamide, linear or branched chain (alkoxycarbonyl)alkyl-carboxamide, linear or branched chain (carboxy)arylalkylcarboxamide, linear or branched chain (alkoxycarbonyl)alkylcarboxamide, an oligoester fragment comprising from 2 to about 20 hydroxy acyl residues, a peptidic fragment comprising from 2 to about 20 amino acyl residues, or a linear or branched chain alkyl or aryl carboxylic ester;
• wherein the carrier is a protein or lipid;
• wherein m is 1, 2 or 3;
• wherein RA, RB and RC are each independently H or methyl;
• and wherein RD, RE and RF are each independently an alkyl glycosidic moiety having the structure:
• wherein each occurrence of A is independently selected from a carbohydrate domain having the structure:
• wherein a, b, c, d, e, f, g, h, i, x, y and z are independently 0, 1, 2 or 3, with the proviso that x, y and z are not simultaneously 0;
• wherein the carbohydrate domain is linked to the respective amino acyl or hydroxy acyl residue by substitution of a side group substituent selected from the group consisting of OH, COOH and NH2;
• wherein R0 is hydrogen, a linear or branched chain alkyl, acyl, arylalkyl or aryl group;
• wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are each independently hydrogen, OH, ORi, NH2, NHCORi, F, CH2OH, CH2ORi, a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group;
• wherein Ri is hydrogen, CHO, COORii, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group or a saccharide moiety having the structure:
• wherein Y and Z are independently NH or O;
• wherein k, l, r, s, t, u, v and w are each independently 0, 1 or 2;
• wherein R10, R11, R12, R13, R14 and R15 are each independently hydrogen, OH, ORiii, NH2, NHCORiii, F, CH2OH, CH2ORiii, or a substituted or unsubstituted linear or branched chain alkyl, (mono-, di- or tri)hydroxyalkyl, (mono-, di- or tri)acyloxyalkyl, arylalkyl or aryl group;
• wherein R16 is hydrogen, COOH, COORii, CONHRii, a substituted or unsubstituted linear or branched chain alkyl or aryl group;
• wherein Riii is hydrogen, CHO, COORiv, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group;
• and wherein Rii and Riv are each independently H, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group;
• and
• wherein each occurrence of n is independently 0-8, whereby, if for each occurrence of n, n=0, at least one occurrence of A has a different structure from other occurrences of A;
• and wherein the n-alkyl glycosidic moiety is either α- or β-linked to an amino acid.