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Four glycoconjugate building blocks for the construction of combinatorial PNA like glycopeptide libraries were prepared in 75-79% yield by condensing tert -butyl N -[2-( N -9-fluorenylmethoxycarbonylamino)ethyl]glycinate (AEG) 5 with 3-oxo-3-(2,3,4,6-tetra- O -acetyl-β-D-glucopyranosylamino)- ( 6a ), 3-oxo-3-(β-D-galactopyranosylamino)- ( 6b ), 3-oxo-3-(2-acetamido-2-deoxy-3,4,6-tetra- O -acetyl-β-D-glucopyranosylamino)- ( 6c ) and 3-oxo-3-(2-acetamido-2-deoxy-3,4,6-tetra- O -acetyl-β-D-galactopyranosylamino)propanoic acid ( 6d) , respectively. The resulting AEG glycoconjugates 1a-d were converted into the corresponding free acids 2a-d in 97-98% yield by treatment with aqueous formic acid. The Fmoc group of compound 1c was removed and the intermediate amine 9 was condensed with 2a to afford the corresponding glycosylated AEG dipeptide 4 in 58% yield. All glycoconjugate building blocks showed the presence of cis and trans rotamers. Compounds 1a , 1b and 4 were subjected to temperature dependent 1 H NMR spectroscopy in order to determine the coalescence temperature which resulted in calculated rotation barriers of 17.9-18.3 kcal/mol for the rotamers.

beilstein journal of organic chemistry

Synthesis and NMR studies of malonyl-linked glycoconjugates of <i>N</i>-(2-aminoethyl)glycine. Building blocks for the construction of combinatorial glycopeptide libraries

Synthesis and NMR studies of malonyl-linked glycoconjugates of N-(2-aminoethyl)glycine. Building blocks for the construction of combinatorial glycopeptide libraries