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Literature summary for 1.13.11.72 extracted from

  • Whitteck, J.T.; Malova, P.; Peck, S.C.; Cicchillo, R.M.; Hammerschmidt, F.; van der Donk, W.A.
    On the stereochemistry of 2-hydroxyethylphosphonate dioxygenase (2011), J. Am. Chem. Soc., 133, 4236-4239.
    View publication on PubMedView publication on EuropePMC

Organism

Organism UniProt Comment Textmining
Streptomyces viridochromogenes Q5IW40
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-2-hydroxyethylphosphonate + O2
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Streptomyces viridochromogenes hydroxymethylphosphonate + formate product is almost racemic ?
(S)-2-hydroxyethylphosphonate + O2
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Streptomyces viridochromogenes hydroxymethylphosphonate + formate product is almost racemic ?
2-hydroxyethylphosphonate + O2 mechanism involves removal of the pro-S hydrogen at C2 and the loss of stereochemical information at C1. Thus, the hydroperoxylation mechanism, previously proposed as the product of a Criegee rearrangement, cannot be operational for conversion of 2-hydroxyethylphosphonate Streptomyces viridochromogenes hydroxymethylphosphonate + formate
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