Related Experiment Video
Updated: May 13, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Synthesis of thioglycoside analogues of maradolipid
Xiaojun Zeng1, Raymond Smith, Xiangming Zhu
1College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China.
Abstract:
We describe here the first synthesis of thioglycoside analogues of maradolipid, based on a new procedure for the synthesis of 1-thiotrehalose developed recently in our laboratories. The challenging α,α-(1→1') thioglycosidic linkage was constructed by Schmidt's inverse procedure in very high yield and excellent stereoselectivity. Subsequent protecting group manipulation and coupling with different fatty acids led smoothly to a group of symmetrical and unsymmetrical thiomaradolipids which would be of high value for biological studies.
Related Concept Videos
Formation of Lipopolysaccharides
Biosynthesis of Lipids
Inhibitors of Gram-positive Cell Wall Synthesis
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

