Synthesis of Zwitterionic 1,1′-Glycosylphosphodiester: A Partial Structure of Galactosamine-Modified Francisella Lipid A | Zendy

David Baum | Zendy; Paul Kosma | Zendy; Alla Zamyatina | Zendy

Open Access

Synthesis of Zwitterionic 1,1′-Glycosylphosphodiester: A Partial Structure of Galactosamine-Modified Francisella Lipid A

Author(s) -

David Baum,

Paul Kosma,

Alla Zamyatina

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501639c

Subject(s) - chemistry , phosphodiester bond , glycosidic bond , lactol , disaccharide , anomer , galactosamine , stereochemistry , phosphoramidite , amide , phosphonate , biochemistry , glucosamine , lactone , enzyme , dna , gene , rna , oligonucleotide

Synthesis of a "double glycosidic" phosphodiester comprising anomeric centers of two 2-amino-2-deoxy-sugars is reported. The carbohydrate epitope of Francisella lipid A modified with α-d-galactosamine at the anomerically linked phosphate has been stereoselectively prepared and coupled to maleimide-activated bovine serum albumin via an amide-linked thiol-terminated spacer group. H-Phosphonate and phosphoramidite approaches have been explored for the coupling of 4,6-DTBS-2-azido-protected GalN lactol and peracetylated spacer-equipped reducing βGlcN(1→6)GlcN disaccharide via phosphodiester linkage. Deprotection conditions preserving the integrity of the labile glycosidic zwitterionic phosphodiester were elaborated.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research