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.
Citations
May 16, 2006·Carbohydrate Research·Mohammed Nurul AminYukishige Ito
Mar 12, 2010·Mass Spectrometry Reviews·David J Harvey
Feb 18, 2015·Chembiochem : a European Journal of Chemical Biology·Akihiro IshiwataYukishige Ito
Oct 4, 2018·Chemistry : a European Journal·Sicheng Lin, Todd L Lowary
Jul 8, 2008·Chemistry, an Asian Journal·Miyuki KoshibaShunichi Hashimoto
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
Mar 7, 2019·Organic & Biomolecular Chemistry·Giulia VessellaEmiliano Bedini
May 18, 2011·The Journal of Organic Chemistry·Jane Kalikanda, Zhitao Li
Apr 10, 2013·The Journal of Organic Chemistry·Shino Manabe, Yukishige Ito
Jul 7, 2020·Chemical Reviews·Asiri A HettikankanamalageDavid Crich