Synthesis of asparagine-linked glycopeptides on a polymeric solid support

The present invention provides a process for synthesizing a glycopeptide having the structure: +TR wherein R1, R2, R3, R4, R5, R6, R7 and R8 are each independently H, OH, OR1, NH2, NHCORi, F, CH2OH, CH2ORi, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group, wh...

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Hauptverfasser: BEEBE, XENIA, DANISHEFSKY, SAMUEL J, ROBERGE, JACQUES
Format: Patent
Sprache:eng
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Zusammenfassung:The present invention provides a process for synthesizing a glycopeptide having the structure: +TR wherein R1, R2, R3, R4, R5, R6, R7 and R8 are each independently H, OH, OR1, NH2, NHCORi, F, CH2OH, CH2ORi, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group, where Ri is H, CHO, CO2Rii, a linear or branched chain alkyl, arylalkyl or aryl group, or an oligosaccharide moiety, etc., wherein R0 is H, a linear or branched chain alkyl, arylalkyl or aryl group; wherein R10 is a substituted or unsubstituted linear or branched chain acyl, arylacyl or aroyl group; wherein R11[x] represents X amino acid side-chains, and denotes position from the N-terminus, and R13[y] represents Y amino acid side-chains, and denotes position from the C-terminus, wherein a, b, c, h, i, j, r, s and t are each independently an integer between about 0 and about 3; wherein m and n are each independently an integer between about 0 and about 5; and wherein x, x'(N), y and y'(N) are each independently an integer between about 0 and,about 25; such glycopeptides being useful as a vaccine for inducing antibodies to human breast cancer cells in an adjuvant therapy therefor. The present invention provides a process for synthesizing a glycopeptide having the structure: +TR wherein R1, R2, R3, R4, R5, R6, R7 and R8 are each independently H, OH, OR1, NH2, NHCORi, F, CH2OH, CH2ORi, or a substituted or unsubstituted linear or branched chain alkyl, arylalkyl or aryl group, where Ri is H, CHO, CO2Rii, a linear or branched chain alkyl, arylalkyl or aryl group, or an oligosaccharide moiety, etc., wherein R0 is H, a linear or branched chain alkyl, arylalkyl or aryl group; wherein R10 is a substituted or unsubstituted linear or branched chain acyl, arylacyl or aroyl group; wherein R11[x] represents X amino acid side-chains, and denotes position from the N-terminus, and R13[y] represents Y amino acid side-chains, and denotes position from the C-terminus, wherein a, b, c, h, i, j, r, s and t are each independently an integer between about 0 and about 3; wherein m and n are each independently an integer between about 0 and about 5; and wherein x, x'(N), y and y'(N) are each independently an integer between about 0 and,about 25; such glycopeptides being useful as a vaccine for inducing antibodies to human breast cancer cells in an adjuvant therapy therefor.