Total
Synthesis of <i>Pseudomonas aeruginosa</i> 1244 Pilin Glycan
via <i>de Novo</i> Synthesis of Pseudaminic
Acid
Han Liu
Yanfeng Zhang
Ruohan Wei
Gloria Andolina
Xuechen Li
10.1021/jacs.7b06055.s001
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_i_Pseudomonas_aeruginosa_i_1244_Pilin_Glycan_via_i_de_Novo_i_Synthesis_of_Pseudaminic_Acid/5378089
Pseudaminic acid (Pse) is a nonulosonic
acid unique to bacterial
species, found as a component of important cell surface glycans and
glycoproteins in various pathogenic species, such as the critical
hospital threat <i>Pseudomonas aeruginosa</i>. Herein we
present the development of a facile and scalable <i>de novo</i> synthesis of Pse and its functionalized derivatives from easily
available Cbz-l-<i>allo</i>-threonine methyl ester
(16 steps in 11% yield). The key reactions in our <i>de novo</i> synthesis involve the diastereoselective glycine thioester
isonitrile-based aldol-type reaction to create the 1,3-<i>anti</i>-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated
Barbier-type allylation. Moreover, we have studied the glycosylation
of the Pse glycosyl donors and identified the structural determinants
for its glycosylation diastereoselectivity, which enabled
us to complete the total synthesis of <i>P. aeruginosa</i> 1244 pilin trisaccharide α-5NβOHC<sub>4</sub>7NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.
2017-08-24 00:00:00
Pseudomonas aeruginosa 1244 Pilin Glycan
Pse glycosyl donors
species
synthesis
hospital threat Pseudomonas aeruginosa
diamino skeleton
diastereo
functionalized derivatives
Total Synthesis
Pseudaminic acid
indium-mediated Barbier-type allylation
cell surface glycans
Novo Synthesis
Fukuyama reduction