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Formal Synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol From D-(+)-Arabitol

Sina I Odejinmi1, Rafael G Rascon, Wyman Chen

  • 1Division of Medical Genetics, Department of Pediatrics, University of Utah School of Medicine, Salt Lake City, UT 84132, U.S.A.

Tetrahedron
|October 11, 2012
PubMed

Insights

Researchers synthesized 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), a key intermediate in microbial isoprenoid biosynthesis. This synthesis advances the study of the non-mevalonate pathway for novel antimicrobial drug development.

Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Microbiology

Background:

  • The non-mevalonate pathway is crucial for isoprenoid biosynthesis in many pathogenic microbes.
  • This pathway, absent in humans, offers a promising target for antimicrobial drug development.
  • 2-C-methyl-D-erythritol-4-phosphate (MEP) and 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME) are key intermediates in this pathway.

Purpose of the Study:

  • To report a formal synthesis of CDP-ME.
  • To facilitate in-depth studies of the non-mevalonate pathway.
  • To provide a foundation for developing new antimicrobial agents targeting microbial isoprenoid biosynthesis.

Main Methods:

  • A novel synthesis of 2-C-Methyl-D-erythritol-4-phosphoric acid was developed.
  • The synthesis started from D-(+)-arabitol.
  • Formal synthesis of CDP-ME was achieved using the synthesized intermediate.

Main Results:

  • Successful synthesis of 2-C-Methyl-D-erythritol-4-phosphoric acid from D-(+)-arabitol.
  • Established a formal synthesis route for CDP-ME.
  • Provided a key intermediate for further research into the non-mevalonate pathway.

Conclusions:

  • The developed synthetic route provides access to CDP-ME, a vital intermediate.
  • This work supports the exploration of the non-mevalonate pathway as a target for novel antimicrobials.
  • Further research can build upon this synthesis to investigate microbial isoprenoid biosynthesis and develop new therapeutic strategies.

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