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Literature summary for 5.4.99.2 extracted from

  • Bito, T.; Yabuta, Y.; Ichiyanagi, T.; Kawano, T.; Watanabe, F.
    A dodecylamine derivative of cyanocobalamin potently inhibits the activities of cobalamin-dependent methylmalonyl-CoA mutase and methionine synthase of Caenorhabditis elegans (2014), FEBS open bio, 4, 722-729 .
    View publication on PubMedView publication on EuropePMC
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Cloned(Commentary)

Cloned (Comment) Organism
gene mmcm-1, quantitative real-time PCR analysis Caenorhabditis elegans

Inhibitors

Inhibitors Comment Organism Structure
cyanocobalamin dodecylamine CN-Cbl dodecylamine, a ribose 5'-carbamate derivative of cyanocobalamin, is absorbed and accumulated to significant levels by Caenorhabditis elegans and is not further metabolized. The dodecylamine derivative does not affect the levels of mRNAs encoding enzymes or proteins involved in intercellular cobalamin metabolism, including methylmalonyl-CoA mutase (mmcm-1), methylmalonic acidemia cobalamin A complementation group (mmaa-1), methylmalonic aciduria cblC type (cblc-1), and methionine synthase reductase (mtrr-1). In contrast, the level of the mRNAs encoding cob(I)alamin adenosyltransferase (mmab-1) is increased significantly and identical to that of cobalamin-deficient Caenorhabditis elegans. The cyanocobalamindodecylamine derivative acts as a potent inhibitor of cobalamin-dependent enzymes and induces severe cobalamin deficiency in Caenorhabditis elegans. The CN-Cbl dodecylamine derivative competitively inhibits the apoenzyme. CN-Cbl dodecylamine has increased affinity for the apoenzyme relative to that of cofactor adenosylcobalamin (AdoCbl). CN-Cbl does not reduce the apo-MCM activity in the presence of AdoCbl Caenorhabditis elegans

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(R)-methylmalonyl-CoA Caenorhabditis elegans
-
 succinyl-CoA
-
 r
(R)-methylmalonyl-CoA Caenorhabditis elegans N2 Bristol
-
 succinyl-CoA
-
 r

Organism

Organism UniProt Comment Textmining
Caenorhabditis elegans Q23381
-
-
Caenorhabditis elegans N2 Bristol Q23381
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(R)-methylmalonyl-CoA
-
 Caenorhabditis elegans succinyl-CoA
-
 r
(R)-methylmalonyl-CoA
-
 Caenorhabditis elegans N2 Bristol succinyl-CoA
-
 r

Synonyms

Synonyms Comment Organism
cobalamin-dependent methylmalonyl-CoA mutase
-
 Caenorhabditis elegans
mmcm-1
-
 Caenorhabditis elegans

Cofactor

Cofactor Comment Organism Structure
adenosylcobalamin AdoCbl, dependent on Caenorhabditis elegans

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0015
-
 cyanocobalamin dodecylamine with apo-enzyme, pH 7.0, temperature not specified in the publication Caenorhabditis elegans

General Information

General Information Comment Organism
metabolism inhibitor cyanocobalamin dodecylamine, a ribose 5'-carbamate derivative of cofactor cyanocobalamin, is absorbed and accumulated to significant levels by Caenorhabditis elegans and is not further metabolized. The dodecylamine derivative does not affect the levels of mRNAs encoding enzymes or proteins involved in intercellular cobalamin metabolism, including methylmalonyl-CoA mutase (mmcm-1), methylmalonic acidemia cobalamin A complementation group (mmaa-1), methylmalonic aciduria cblC type (cblc-1), and methionine synthase reductase (mtrr-1). In contrast, the level of the mRNAs encoding cob(I)alamin adenosyltransferase (mmab-1) is increased significantly and identical to that of cobalamin-deficient Caenorhabditis elegans. The cyanocobalamindodecylamine inhibitor of cobalamin-dependent enzymes induces severe cobalamin deficiency in Caenorhabditis elegans. Cobalamin deficiency decreases the egg-laying rates and prolongs the life cycle of the worms, phenotype overview Caenorhabditis elegans