Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9
2011

Synthesis of a Tetrasaccharide from Shigella boydii

publication Evidence: high

Author Information

Author(s): Santra Abhishek, Misra Anup Kumar, Flitsch Sabine

Primary Institution: Bose Institute, Division of Molecular Medicine, Kolkata, India

Hypothesis

A convergent chemical synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 can be achieved using a [2 + 2] block glycosylation strategy.

Conclusion

The study successfully developed a convenient synthetic strategy for the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9.

Supporting Evidence

  • A convenient synthesis of the tetrasaccharide was achieved in excellent yield.
  • The use of a block glycosylation strategy reduced the number of protection–deprotection steps.
  • High yielding and stereoselective glycosylation steps were employed.

Takeaway

The researchers figured out how to make a special sugar that can help fight a type of bacteria that causes diarrhea.

Methodology

The synthesis involved a [2 + 2] block glycosylation strategy and various reaction methodologies for protecting group manipulations.

Digital Object Identifier (DOI)

10.3762/bjoc.7.137

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