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
Hauptverfasser: Guo, Lina, Liu, Taibao, Chen, Kai, Song, Tianbang, Wang, Peng George, Zhao, Wei
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Sprache:eng
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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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01220h