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Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics

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2015

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John, Franklin

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The Journal of Organic Chemistry. 2015, 80(15), pp. 7477-7485. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.5b01049

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Sugar diamino acids (SDAs), which differ from the widely used sugar amino acids in the presence of a second amino group connected to the carbohydrate core, share structural features of both amino acids and carbohydrates. They can be used for the preparation of linear and branched amide-linked oligosaccharide mimetics. Such oligomers carry free amino groups, which are positively charged at neutral pH, in a spatially defined way and, thus, represent a potential class of aminoglycoside mimetics. We report here the first examples of orthogonally protected furanoid SDAs and their use in solid-phase synthesis. Starting from d-glucose, we developed a divergent synthetic route to three derivatives of 3,5-diamino-3,5-dideoxy-d-ribofuranose. These building blocks are compatible with solid-phase peptide synthesis following the 9-fluorenylmethoxycarbonyl (Fmoc) strategy, which we demonstrate by the synthesis of an SDA tetramer.

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ISO 690JOHN, Franklin, Valentin WITTMANN, 2015. Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics. In: The Journal of Organic Chemistry. 2015, 80(15), pp. 7477-7485. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.5b01049
BibTex
@article{John2015-08-07Ortho-32331,
  year={2015},
  doi={10.1021/acs.joc.5b01049},
  title={Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics},
  number={15},
  volume={80},
  issn={0022-3263},
  journal={The Journal of Organic Chemistry},
  pages={7477--7485},
  author={John, Franklin and Wittmann, Valentin}
}
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