Branched N-Glycans for a Better Understanding of Modified Proteins

  • ChemPubSoc Europe Logo
  • Author: Chemistry – An Asian Journal
  • Published Date: 09 June 2018
  • Source / Publisher: Chemistry – An Asian Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Branched N-Glycans for a Better Understanding of Modified Proteins

Glycosylation, i.e., attaching carbohydrates, is a common protein modification. Asparagine-linked polysaccharides (N-glycans) are one such type of carbohydrate. They have high structural and bio-functional diversities. Branched N-glycans which contain a bisecting N-acetylglucosamine (GlcNAc, pictured in the box), for example, have various biological functions. A sufficient supply of this type of N-glycan is required to investigate the biological functions of the bisecting GlcNAc.


Koichi Fukase, Osaka University, Japan, and colleagues have synthesized an N-glycan which contains a bisecting GlcNAc (pictured) by a convergent synthetic route via [4+2] and [6+2] glycosylations. This synthetic strategy reduced the number of reaction steps. The key glycosylations were challenging in terms of yields and selectivity due to steric hindrance at the glycosylation site and a lack of neighboring-group participation. The team enhanced the yields of these reactions by stabilizing the oxocarbenium ion intermediate through ether coordination. Glycosyl-donor protecting groups were used to achieve the desired selectivity.


The developed approach provides a universal synthetic strategy for the efficient synthesis of various N-glycans which could accelerate functional studies of these compounds.


 

Article Views: 700

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH