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April 15, 2026Organic Letters2 citations

Synthesis of Conjugation-Ready Trisaccharide Repeating Units of Multidrug-Resistant Pathogen Acinetobacter baumannii MG1 and Strain 24

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ASAishwarya ShelkeKSKartikey SinghSKSuvarn S. Kulkarni

Key Points

  • The aim is to synthesize conjugation-ready trisaccharide repeating units from clinical isolates of Acinetobacter baumannii.
  • Total synthesis of trisaccharide repeating units from strains MG1 and strain 24.
  • Addressed stereoselective installation of glycosidic linkage.
  • Achieved conformational switching of the pyranose ring to enhance reactivity.
  • Successfully synthesized trisaccharide repeating units with a common framework.
  • Demonstrated efficient stereoselective installation of 1,2-cis glycosidic linkage.

Abstract

We report the first total synthesis of conjugation-ready trisaccharide repeating units from Acinetobacter baumannii clinical isolates MG1 and strain 24, both featuring the same trisaccharide framework. A key synthetic challenge addressed here is the stereoselective installation of a 1,2-cis glycosidic linkage with a poorly nucleophilic axially oriented C4-OH of the d-GalNAcA acceptor, which was efficiently achieved by conformational switching of the pyranose ring from 4C1 to 1C4 leading to enhanced reactivity.

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Cite This Study

Shelke et al. (2026) studied this question.

synapsesocial.com/papers/69df2c62e4eeef8a2a6b171ehttps://doi.org/10.1021/acs.orglett.6c01063
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