Total Synthesis of the Conjugation-Ready Tetrasaccharide Repeating Unit of Shewanella japonica Type Strain KMM 3299T

Org Lett. 2024 May 24;26(20):4346-4350. doi: 10.1021/acs.orglett.4c01354. Epub 2024 May 9.

Abstract

Here we report the first total synthesis of the conjugation-ready tetrasaccharide repeating unit of Shewanella japonica type strain KMM 3299T. The presence of rare deoxyamino sugars and installation of three consecutive 1,2-cis glycosidic linkages makes the synthesis formidable. The challenging late-stage oxidation was overcome by using a galacturonate donor. The total synthesis was completed via a longest linear sequence of 22 steps in an overall yield of 3.5% starting from d-mannose.

MeSH terms

  • Carbohydrate Sequence
  • Mannose / chemistry
  • Molecular Structure
  • Oligosaccharides* / chemical synthesis
  • Oligosaccharides* / chemistry
  • Oxidation-Reduction
  • Shewanella* / chemistry

Substances

  • Oligosaccharides
  • Mannose