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Literature summary for 2.1.1.68 extracted from

  • Green, A.R.; Lewis, K.M.; Barr, J.T.; Jones, J.P.; Lu, F.; Ralph, J.; Vermerris, W.; Sattler, S.E.; Kang, C.
    Determination of the structure and catalytic mechanism of Sorghum bicolor caffeic acid O-methyltransferase and the structural impact of three brown midrib12 mutations (2014), Plant Physiol., 165, 1440-1456.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
apo-form and binary complex with S-adenosyl-methionine, to 2.1 and 2.8 A resolution, respectively, and molecular modeling of the ternary complex structure with 5-hydroxyconiferaldehyde Sorghum bicolor

Inhibitors

Inhibitors Comment Organism Structure
5-hydroxyconiferaldehyde
-
Sorghum bicolor

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.00086
-
5-hydroxyconiferaldehyde pH 6.5, 22°C Sorghum bicolor
0.0011
-
5-hydroxyconiferaldehyde pH 7.5, 22°C Sorghum bicolor
0.012
-
3,4-dihydroxy-trans-cinnamate pH 6.5, 22°C Sorghum bicolor
0.017
-
S-adenosyl-L-methionine pH 6.5, 22°C Sorghum bicolor

Organism

Organism UniProt Comment Textmining
Sorghum bicolor C5YH12
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information random bi-bi mechanism. The observed reactivity hierarchy among 4,5-dihydroxy-3-methoxycinnamyl (and 3,4-dihydroxycinnamyl) aldehyde, alcohol, and acid substrates arises from the ability of the aldehyde to stabilize the anionic intermediate that results from deprotonation of the 5-hydroxyl group by histidine-267. Sinapaldehyde is the preferential product, as demonstrated by its low Km for 5-hydroxyconiferaldehyde. Unlike its acid and alcohol substrates, the aldehydes exhibit product inhibition, due to nonproductive binding of the S-cis-form of the aldehydes inhibiting productive binding of the S-trans-form Sorghum bicolor ?
-
?
S-adenosyl-L-methionine + 3,4-dihydroxy-trans-cinnamate
-
Sorghum bicolor S-adenosyl-L-homocysteine + 3-methoxy-4-hydroxy-trans-cinnamate
-
?
S-adenosyl-L-methionine + 5-hydroxyconiferaldehyde
-
Sorghum bicolor S-adenosyl-L-homocysteine + 5-methoxyconiferaldehyde
-
?

Synonyms

Synonyms Comment Organism
Sb07g003860
-
Sorghum bicolor

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0027
-
5-hydroxyconiferaldehyde pH 7.5, 22°C Sorghum bicolor
0.01
-
5-hydroxyconiferaldehyde pH 6.5, 22°C Sorghum bicolor