Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• selective IgG antibodies that are cross-reactive with native MUC1 epitopes on MCF-7 human cancer cells. Keywords: cancer immunotherapy; fluorinated carbohydrates; glycoconjugates; MUC1; TACA; Introduction Since cancer has advanced to one of the leading causes of death in economical developed countries

• cells from healthy ones by means of tumor-associated antigens (TACA), e.g., partial structures of the mucin glycoprotein MUC1 [6][7]. Cancer-associated MUC1 is characterized by the presence of specifically altered carbohydrate side chains in its extracellular tandem-repeat domain due to fundamental

• host [28]. Earlier studies proved that non-natural TACAs can be indeed highly immunogenic [29][30][31][32], although the elicited antibodies often failed to cross-react with the natural glycan. To overcome this drawback, the use of synthetic carbohydrate-based vaccines with TACA analogs [33][34] in

Synthesis of 4” manipulated Lewis X trisaccharide analogues

• Christopher J. Moore and
• France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2012, 8, 1134–1143, doi:10.3762/bjoc.8.126

• ) have been shown to recognize this Lex antigenic determinant as it exists in the hexasaccharide [1][2][3][4][5][6]. Therefore, as our group embarks on the development of a therapeutic anticancer vaccine utilizing the Tumor Associated Carbohydrate Antigen (TACA) dimLex as a target, an important factor to

Synthesis of glycosylated β³-homo-threonine conjugates for mucin-like glycopeptide antigen analogues

• Florian Karch and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2010, 6, No. 47, doi:10.3762/bjoc.6.47

• carbohydrate antigens (TACA) have proven to be important target structures for the development of molecularly defined anti-cancer vaccines. The strategic incorporation of β-amino acid building blocks into such mucin-type sequences offers the potential to create pseudo-glycopeptide antigens with improved

• tumourigenic process and as target structures for cancer immunotherapy [5]. Over the last years, mucin-type glycopeptides decorated with tumour-associated carbohydrate antigens (TACA) have been shown to trigger strong humoral immunity within molecularly defined vaccine prototypes [6][7][8][9][10]. However, the

• instance, stable TACA mimics comprising C-glycosides [11][12][13][14], S-glycosides [15][16][17][18][19] and deoxyfluoro sugars [20] have been used to circumvent hydrolytic degradation by endogenous glycosidases. In principle, antigenicity of the artificial TACA derivatives should be enhanced by minor

Convergent syntheses of Le^X analogues

• An Wang,
• Jenifer Hendel and
• France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2010, 6, No. 17, doi:10.3762/bjoc.6.17

• efficient and convergent preparation of these three Lex analogues. Keywords: Birch reduction; convergent synthesis; desulfurization; Lewis X; Introduction Our group is involved in the design of new anti-cancer vaccines based on the Tumor Associated Carbohydrate Antigen (TACA) dimeric Lex (dimLex) [1][2][3