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Literature summary for 3.5.1.108 extracted from

  • Robinet, J.J.; Gauld, J.W.
    DFT investigation on the mechanism of the deacetylation reaction catalyzed by LpxC (2008), J. Phys. Chem. B, 112, 3462-3469.
    View publication on PubMed
Search for more literature for 3.5.1.108

Metals/Ions

Metals/Ions Comment Organism Structure
Zn2+ the substrate preferentially coordinates to the active site Zn2+ via its carbonyl oxygen between a Zn2+-bound H2O and an adjacent threonine. Furthermore, upon substrate binding a nearby Glu78 residue is found to readily deprotonate the remaining Zn2+-bound H2O Aquifex aeolicus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O Aquifex aeolicus LpxC is a key enzyme in the biochemical synthesis of Lipid A UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
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Organism

Organism UniProt Comment Textmining
Aquifex aeolicus
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O LpxC is a key enzyme in the biochemical synthesis of Lipid A Aquifex aeolicus UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
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UDP-3-O-((R)-3-hydroxymyristoyl)-N-acetylglucosamine + H2O the mechanism of LpxC proceeds via four steps: (1) initial hydroxylation of the substrates’ carbonyl carbon to give a gem-diolate intermediate, (2) protonation of the amide nitrogen by the histidine His265-H+, (3) a barrier-less change in the active site-intermediate hydrogen-bond network and finally, (4) C-N bond cleavage. The rate-determining step of the mechanism of LpxC is the initial hydroxylation while the final C-N bond cleavage occurs with an overall barrier of 23.6 kJ/mol. LpxC uses a general acid/base pair mechanism as indicated by the fact that both His265-H+ and Glu78 are accordingly involved Aquifex aeolicus UDP-3-O-((R)-3-hydroxymyristoyl)-D-glucosamine + acetate
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Synonyms

Synonyms Comment Organism
LpxC
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 Aquifex aeolicus