Issue 37, 2014
From the journal:

Organic & Biomolecular Chemistry

Facile synthesis of 5-hydroxy-l-lysine from d-galactose as a chiral-precursor†

Lina Guo,a   Taibao Liu,a   Kai Chen,b   Tianbang Song,a   Peng George Wang*ac  and  Wei Zhao*a  

* Corresponding authors

a State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, PR China
E-mail: wzhao@nankai.edu.cn, pwang@nankai.edu.cn
Fax: +86 22 23507760

b Laboratory of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, PR China

c The Department of Chemistry, Georgia State University, Atlanta, GA 30302, USA

Abstract

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.

Graphical abstract: Facile synthesis of 5-hydroxy-l-lysine from d-galactose as a chiral-precursor

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C4OB01220H
Article type
Paper
Submitted
13 Jun 2014
Accepted
23 Jul 2014
First published
29 Jul 2014

Org. Biomol. Chem., 2014,12, 7310-7317

Permissions

Request permissions

Facile synthesis of 5-hydroxy-L-lysine from D-galactose as a chiral-precursor

L. Guo, T. Liu, K. Chen, T. Song, P. G. Wang and W. Zhao, Org. Biomol. Chem., 2014, 12, 7310 DOI: 10.1039/C4OB01220H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements