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

ABSTRACT: 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 <

SUBMITTER: Norrlinger M 

PROVIDER: S-EPMC5082468 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature