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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-?-D-glucopyranosylamino)- (6a), 3-oxo-3-(?-D-galactopyranosylamino)- (6b), 3-oxo-3-(2-acetamido-2-deoxy-3,4,6-tetra-O-acetyl-?-D-glucopyranosylamino)- (6c) and 3-oxo-3-(2-acetamido-2-deoxy-3,4,6-tetra-O-acetyl-?-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 1H 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.

SUBMITTER: Norrlinger M 

PROVIDER: S-EPMC5082468 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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

Nörrlinger Markus M   Hafner Sven S   Ziegler Thomas T  

Beilstein journal of organic chemistry 20160830


Four glycoconjugate building blocks for the construction of combinatorial PNA like glycopeptide libraries were prepared in 75-79% yield by condensing <i>tert</i>-butyl <i>N</i>-[2-(<i>N</i>-9-fluorenylmethoxycarbonylamino)ethyl]glycinate (AEG) <b>5</b> with 3-oxo-3-(2,3,4,6-tetra-<i>O</i>-acetyl-β-D-glucopyranosylamino)- (<b>6a</b>), 3-oxo-3-(β-D-galactopyranosylamino)- (<b>6b</b>), 3-oxo-3-(2-acetamido-2-deoxy-3,4,6-tetra-<i>O</i>-acetyl-β-D-glucopyranosylamino)- (<b>6c</b>) and 3-oxo-3-(2-acet  ...[more]

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