Facile synthesis of 5-hydroxy-L-lysine from D-galactose as a chiral-precursor
A concise synthesis of (2S,5R) and (2S,5S)-5-hydroxy-lysine was achieved by utilizing D-galactose as a chiral-precursor with stereo retention. This synthetic strategy showcased the potential of utilizing carbohydrates as starting materials to prepare amino acids. Using the diazido intermediate, the...
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Veröffentlicht in: | Organic & biomolecular chemistry 2014-10, Vol.12 (37), p.7310-7317 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | A concise synthesis of (2S,5R) and (2S,5S)-5-hydroxy-lysine was achieved by utilizing D-galactose as a chiral-precursor with stereo retention. This synthetic strategy showcased the potential of utilizing carbohydrates as starting materials to prepare amino acids. Using the diazido intermediate, the derived β-D-galactopyranosyl and α-D-glucopyranosyl-(1→2)-β-D-galactosyl moieties were synthesized. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c4ob01220h |