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

• bioavailability for tumour immunotherapy. Towards this end, TN and TF antigen conjugates O-glycosidically linked to Fmoc-β3-homo-threonine were prepared in good yield via Arndt–Eistert homologation of the corresponding glycosyl α-amino acid derivative. By incorporation of TN-Fmoc-β3hThr conjugate into the 20

• increased biological half-life. Keywords: glycopeptide; glycosylamino acids; β3-homo-threonine; MUC1 antigens; solid-phase synthesis; Introduction Glycosylation is the predominant co- and post-translational modification in higher organisms responsible for tailoring and fine-tuning of the activity of

• -3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-galactopyranosyl]-β3-homo-threonine 2a: Procedure A: The synthesis followed the general procedures GP1 and GP2. Amounts: 150 mg (0.22 mmol) 1a. Yield: 90 mg (0.13 mmol), 60%, colourless amorphous solid. Analytical RP-HPLC (Luna, MeCN–H2O + 0.1% TFA, 20:80 → 60:40