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Biosynthesis of Polysaccharides01:26

Biosynthesis of Polysaccharides

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Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
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Published on: November 25, 2017

CMP substitutions preferentially inhibit polysialic acid synthesis.

Tatsuo Miyazaki1, Kiyohiko Angata, Peter H Seeberger

  • 1Tumor Microenvironment Program, Glycobiology Unit, Cancer Research Center, Burnham Institute for Medical Research, La Jolla, CA 92037, USA.

Glycobiology
|December 14, 2007
PubMed
Summary

New CMP derivatives, 2'-O-methyl CMP and 5-methyl CMP, were synthesized to inhibit sialyltransferases. These compounds effectively reduced polysialic acid expression on cells, offering a new tool for studying carbohydrate synthesis and function.

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Area of Science:

  • Biochemistry
  • Glycobiology
  • Cell Biology

Background:

  • Cell surface carbohydrates are crucial for biological processes.
  • Sialyltransferases play key roles in glycosylation, but their functions are not fully understood.
  • Existing methods for inhibiting glycosylation have limitations.

Purpose of the Study:

  • To synthesize novel cytidylmonophosphate (CMP) derivatives: 2 -O-methyl CMP and 5-methyl CMP.
  • To investigate the inhibitory effects of these derivatives on various sialyltransferases.
  • To explore the potential of these derivatives in modulating cell surface carbohydrate expression.

Main Methods:

  • Chemical synthesis of 2 -O-methyl CMP and 5-methyl CMP.
  • Enzyme assays to test inhibition of alpha2,3-sialyltransferases (ST3Gal-III, ST3Gal-IV), alpha2,6-sialyltransferase (ST6Gal-I), and alpha2,8-sialyltransferases (ST8Sia-II, ST8Sia-III, ST8Sia-IV).
  • Cell culture experiments with Chinese hamster ovary (CHO) cells to assess polysialic acid expression.

Main Results:

  • 2 -O-methyl CMP potently inhibited ST3Gal-III, ST3Gal-IV, ST8Sia-II, ST8Sia-III, and ST8Sia-IV, similar to CMP.
  • 5-methyl CMP moderately inhibited ST3Gal-III, ST3Gal-IV, ST6Gal-I, ST8Sia-II, ST8Sia-III, and ST8Sia-IV.
  • Both CMP derivatives reduced polysialic acid expression on CHO cell surfaces and NCAM.

Conclusions:

  • 2 -O-methyl CMP and 5-methyl CMP are effective inhibitors of specific sialyltransferases, particularly polysialyltransferases.
  • These novel CMP derivatives can be utilized in vitro and in vivo to study sialyltransferase functions.
  • The findings provide a valuable tool for investigating the roles of specific carbohydrate structures in biological processes.