A stereoselective 1,2-cis glycosylation toward the synthesis of a novel N-linked glycan from the Gram-negative bacterium, Campylobacter jejuni

Carbohydrate Research
Akihiro IshiwataYukishige Ito

Abstract

It has been shown that certain prokaryotes, such as Campylobacter jejuni, have asparagine (Asn)-linked glycoproteins. However, the structures of their glycans are distinct from those of eukaryotic origin. They consist of a bacillosamine residue linked to Asn, an alpha-(1-->4)-GalpNAc repeat, and a branching beta-Glcp residue. In this paper, we describe a strategy for the stereoselective construction of the alpha-(1-->4)-GalpNAc repeat of a C. jejuni N-glycan, utilizing a pentafluoropropionyl (PFP) group as a temporary protective group of the C-4 OH group of the GalpN donor. The strategy was applied to the synthesis of the hexasaccharide alpha-GalpNAc-(1-->4)-alpha-GalpNAc-(1-->4)-[beta-Glcp-(1-->3)]-alpha-GalpNAc(1-->4)-alpha-GalpNAc-(1-->4)-GalpNAc.

References


❮ Previous
Next ❯

Citations

May 16, 2006·Carbohydrate Research·Mohammed Nurul AminYukishige Ito
Oct 4, 2018·Chemistry : a European Journal·Sicheng Lin, Todd L Lowary
Jan 21, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Bozhena S KomarovaNikolay E Nifantiev
Aug 15, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Archanamayee Behera, Suvarn S Kulkarni
Apr 5, 2014·Natural Product Reports·Madhu Emmadi, Suvarn S Kulkarni
Apr 10, 2013·The Journal of Organic Chemistry·Shino Manabe, Yukishige Ito

❮ Previous
Next ❯

Related Concepts

Related Feeds

Cardiac Glycosides

Cardiac glycosides are a diverse family of naturally derived compounds that bind to and inhibit na+/k+-atpase. Discover the latest research on cardiac glycosides heres.

Campylobacteriosis (ASM)

Campylobacteriosis is caused by the bacteria Campylobacter jejuni and is a common cause of gastroenteritis in humans. Discover the latest research on Campylobacteriosis here.