Open AccessManual and Automated Syntheses of the N-Linked Glycoprotein Core Glycans
Author(s) -
Salvatore G. Pistorio,
Scott A. Geringer,
Keith J. Stine,
Alexei V. Demchenko
Publication year - 2019
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.8b03056
Subject(s) - glycan , aglycone , core (optical fiber) , chemistry , linkage (software) , glycoprotein , combinatorial chemistry , stereochemistry , computer science , computational biology , biochemistry , biology , glycoside , gene , telecommunications
Presented herein are two complementary approaches to the synthesis of the core N-glycan pentasaccharide. The first, a traditional manual approach in solution, makes use of the H-bond-mediated aglycone delivery method for the highly diastereoselective introduction of the β-mannosidic linkage at room temperature. The synthesis of the core pentasaccharide was also accomplished using an high-performance liquid chromatography-assisted automated approach. The overall assembly was swift (8 h) and efficient (31%).