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Literature summary for 4.1.2.19 extracted from

  • Calveras, J.; Egido-Gabas, M.; Gomez, L.; Casas, J.; Parella, T.; Joglar, J.; Bujons, J.; Clapes, P.
    Dihydroxyacetone phosphate aldolase catalyzed synthesis of structurally diverse polyhydroxylated pyrrolidine derivatives and evaluation of their glycosidase inhibitory properties (2009), Chemistry, 15, 7310-7328.
    View publication on PubMed

Organism

Organism UniProt Comment Textmining
Escherichia coli P32169
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2S,3S)-3-methyl-1-oxopentane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-((S)-sec-butyl)-3,4-diol + N-ethyl-(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-((S)-sec-butyl)-3,4-diol product ratio 55:45 ?
(R)-1-oxobutane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol product ratio 48:30:11:11 ?
(R)-1-oxohexane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)-pyrrolidine-5-propyl-3,4-diol product ratio 28:63:5:5 ?
(R)-1-oxopentane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol product ratio 44:34:11:10 ?
(R)-3-methyl-1-oxobutane-2-benzylcarbamate
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Escherichia coli (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-isopropyl-3,4-diol
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?
(R)-4-methyl-1-oxopentane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol product ratio 32:43:16.9 ?
(S)-1-oxo-3-phenylpropan-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-benzyl-3,4-diol
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?
(S)-1-oxobutane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol
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?
(S)-1-oxohexane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-butyl-3,4-diol + (2S,3S,4R,5S)-2-(hydroxymethyl)pyrrolidine-5-butyl-3,4-diol product ratio 93:7 ?
(S)-1-oxopentane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol
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?
(S)-3-methyl-1-oxobutane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isopropyl-3,4-diol + N-ethyl-(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isopropyl-3,4-diol product ratio 84:16 ?
(S)-4-methyl-1-oxopentane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + (2S,3S,4R,5S)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + N-ethyl-(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol product ratio 71:6:23 ?
2-methyl-1-oxopropane-2-benzylcarbamate
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Escherichia coli (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-5-dimethyl-3,4-diol + (2R,3S,4R)-2-(hydroxymethyl)pyrrolidine-5-dimethyl-3,4-diol product ratio 44:56 ?
additional information RhuA is highly stereoselective with (S)-N-Cbz-2-aminoaldehydes (90-100% syn (i.e., 3R,4S) adduct), whereas those with R configuration give mixtures of anti/syn adducts, for iPr and iBu substituents, RhuA furnishes the anti adduct with high stereoselectivity Escherichia coli ?
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?

Synonyms

Synonyms Comment Organism
L-Rhamnulose-1-phosphate aldolase
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Escherichia coli
RhuA
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Escherichia coli