N-acetylmuramic acid

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N-acetylmuramic acid (systematic name: 2-Acetamido-3-O-[(1R)-1-carboxyethyl]-2-deoxy-D-glucopyranose)[1], along with N-acetylglucosamine, act as subunits to the peptidoglycan cell walls in gram positive and negative bacteria. In the biosynthesis of the cell wall, the N-acetylmuramic acid (MurNAc) and N-acetylglucosamine (GlcNAc) alternates when the units are cross-linked to the existing peptidoglycan layer[2]. The synthesis of N-acetylmuramic acid occurs in two stages. In the first step, N-acetylglucosamine reacts with phosphoenolpyruvate and in an addition reaction, the enolpyruvate from phosphoenolpyruvate is attached to N-acetylglucosamine. This step is catalysed by transferase MurA to produce N-aminoglucosamine-enolpyruvate. In the second stage, enolpyruvate in N-aminoglucosamine-enolpyruvate is reduced by reductase MurB and NADPH to convert N-aminoglucosamine-enolpyruvate to N-acetylmuramic acid[3].

References

  1. ↑ CSID:4575341, http://www.chemspider.com/Chemical-Structure.4575341.html (accessed 10:58, Nov 30, 2017)
  2. ↑ Jean van Heijenoort; Formation of the glycan chains in the synthesis of bacterial peptidoglycan, Glycobiology, Volume 11, Issue 3, 1 March 2001, Pages 25R–36R
  3. ↑ https://doi.org/10.1016/B978-0-12-374546-0.00016-X
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