Synthesis of the tetrasaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100 having rare D-Quip3NAc.

Synthesis of the tetrasaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100 having rare D-Quip3NAc.
Carbohydr Res. 2020 Feb 19;489:107955
Authors: Bera M, Mukhopadhyay B
Abstract
Chemical synthesis of the complex tetrasaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100 is accomplished in the form of its 2-aminoethyl glycoside to leave the scope for further glycoconjugate formation without hampering the anomeric stereochemistry. A [2 + 2] strategy is followed to complete the total synthesis and a late stage TEMPO mediated oxidation is used to install the required uronic acid. A radical mediated 6-deoxygenation with subsequent protecting group manipulation strategy is used for the preparation of the rare D-FucpNAc and D-Quip3NAc derivatives from suitable d-glucosamine derivatives.
PMID: 32088501 [PubMed - as supplied by publisher]

Source: Carbohydrate Research - February 18, 2020 Category: Genetics & Stem Cells Authors: Bera M, Mukhopadhyay B Tags: Carbohydr Res Source Type: research