Information on EC 1.1.1.306 - S-(hydroxymethyl)mycothiol dehydrogenase:
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The lowest common taxonomy group for this enzyme is: Actinomycetales

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EC NUMBERCOMMENTARY
1.1.1.306-

RECOMMENDED NAMEGeneOntology No.
S-(hydroxymethyl)mycothiol dehydrogenase-

REACTIONREACTION DIAGRAMCOMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
S-(hydroxymethyl)mycothiol + NAD+ = S-formylmycothiol + NADH + H+
show the reaction diagram		----

REACTION TYPEORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
oxidation----
redox reaction----
reduction----

PATHWAYKEGG LinkMetaCyc Link
formaldehyde oxidation III (mycothiol-dependent)-PWY1G-170

SYSTEMATIC NAMEIUBMB Comments
S-(hydroxymethyl)mycothiol:NAD+ oxidoreductaseS-hydroxymethylmycothiol is believed to form spontaneously from formaldehyde and mycothiol. This enzyme oxidizes the product of this spontaneous reaction to S-formylmycothiol, in a reaction that is analogous to EC 1.1.1.284, S-(hydroxymethyl)glutathione dehydrogenase.

SYNONYMSORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
FD-FA1DHAmycolatopsis methanolica--288324
glutathione-independent formaldehyde dehydrogenase----
MD-FALDH----
MSH-dependent formaldehyde dehydrogenaseMycobacterium smegmatis--654527
MSH-dependent formaldehyde dehydrogenaseNocardia sp.--690518
NAD/factor-dependent formaldehyde dehydrogenase----

CAS REGISTRY NUMBERCOMMENTARY
192140-85-5-

ORGANISMCOMMENTARYLITERATURESEQUENCE CODESEQUENCE DB SOURCE
Amycolatopsis methanolica-288322, 288323, 288324--Manually annotated by BRENDA team
Mycobacterium smegmatisstrain mc2654527--Manually annotated by BRENDA team
Mycobacterium smegmatis mc2strain mc2654527--Manually annotated by BRENDA team
Nocardia sp.strain NRRL 5646690518--Manually annotated by BRENDA team
Nocardia sp. NRRL 5646strain NRRL 5646690518--Manually annotated by BRENDA team
Rhodococcus erythropolis-288322--Manually annotated by BRENDA team

GENERAL INFORMATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SUBSTRATEPRODUCT                      REACTION DIAGRAMORGANISM UNIPROT ACCESSION NO. COMMENTARY/
Substrate		 LITERATURE/
Substrate		 COMMENTARY/
Product		 LITERATURE/
Product		 Reversibility
r=reversible
ir=irreversible
?=not specified
1-butanol + NAD+n-butanal + NADH
show the reaction diagram		Amycolatopsis methanolica--288324-288324?
12-hydroxydodecanoic acid + NADH? + NAD+
show the reaction diagram		Amycolatopsis methanolica--288324-288324?
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Rhodococcus erythropolis--288322-288322?
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Amycolatopsis methanolica--288324-288324-
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Amycolatopsis methanolica--288322-288322?
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Amycolatopsis methanolica--288323-288323?
mycothiol + NAD+? + NADH + H+
show the reaction diagram		Nocardia sp.--690518--?
S-hydroxymethylmycothiol + NAD+formic acid + mycothiol + NADH + ?
show the reaction diagram		Mycobacterium smegmatis-rapid-equilibrium ordered mechanism654527--?
S-nitrosomycothiol + NADH?
show the reaction diagram		Mycobacterium smegmatis-decomposition with a sequential mechanism, enzyme reduces the nitroso group to the oxidation level of nitroxyl654527--?

NATURAL SUBSTRATESNATURAL PRODUCTSREACTION DIAGRAMORGANISM UNIPROT ACCESSION NO.COMMENTARY SUBSTRATELITERATURE
(Substrate)		COMMENTARY PRODUCTLITERATURE
(Product)
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Rhodococcus erythropolis--288322-288322
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Amycolatopsis methanolica--288324-288324
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Amycolatopsis methanolica--288322-288322
formaldehyde + 1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol + NAD+S-formylmycothiol + NADH
show the reaction diagram		Amycolatopsis methanolica--288323-288323

COFACTORORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATUREIMAGE
1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositolAmycolatopsis methanolica, Rhodococcus erythropolis-high specificity for mycothiol; mycothiol288322 2D-image
1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositolAmycolatopsis methanolica-mycothiol288323 2D-image
NAD+Amycolatopsis methanolica--288322, 288323, 288324 2D-image
NAD+Rhodococcus erythropolis--288322 2D-image
NAD+Mycobacterium smegmatis--654527 2D-image
NAD+Nocardia sp.--690518 2D-image

METALS and IONS ORGANISM UNIPROT ACCESSION NO.COMMENTARY LITERATURE
Zn2+Amycolatopsis methanolica-6 atoms Zn/enzyme molecule288324

INHIBITORSORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
1,10-phenanthrolineAmycolatopsis methanolica-80% inhibition at 5 mM288324 2D-image
2-(cyclohexylamino)ethanesulfonic acid-NaOHAmycolatopsis methanolica-25 mM at pH 9.0: 80% of the activity compared to 0.1 M diphosphate, pH 9.0288324-
acetaldehydeAmycolatopsis methanolica--288322 2D-image
acetaldehydeAmycolatopsis methanolica-15% inhibition at 1 mM288324 2D-image
Cu2+Amycolatopsis methanolica-complete inhibition at 1 mM288324 2D-image
Glycine-NaOHAmycolatopsis methanolica-100 mM at pH 9.0: 40% of the activity compared to 0.1 M diphosphate, pH 9.0288324 2D-image
Hg2+Amycolatopsis methanolica-complete inhibition at 0.1 mM288324 2D-image
KCNAmycolatopsis methanolica-55% inhibition at 2 mM288324 2D-image
Na2B4O7-HClAmycolatopsis methanolica-100 mM at pH 9.0: no activity288324 2D-image
Tris-HClAmycolatopsis methanolica-50 mM at pH 9.0: 80% of the activity compared to 0.1 M diphosphate, pH 9.0288324 2D-image

ACTIVATING COMPOUNDORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
factorAmycolatopsis methanolica-unidentified factor that is required for maximal activity with formaldehyde as substrate, only 4% activity in its absence, oxidation of alcohols do not require the factor288324-
formaldehydeNocardia sp.--690518 2D-image
methanolAmycolatopsis methanolica-can replace an unidentified activating factor288324 2D-image

KM VALUE [mM]KM VALUE [mM] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
84-1-butanolAmycolatopsis methanolica--288324 2D-image
3.4-1-HexanolAmycolatopsis methanolica--288324 2D-image
1.2-1-OctanolAmycolatopsis methanolica--288324 2D-image
26.5-1-PentanolAmycolatopsis methanolica--288324 2D-image
324-1-PropanolAmycolatopsis methanolica--288324 2D-image
1.7-12-Hydroxydodecanoic acidAmycolatopsis methanolica--288324 2D-image
343-ethanolAmycolatopsis methanolica--288324 2D-image
9.6-formaldehydeAmycolatopsis methanolica--288324 2D-image
0.0173-mycothiolMycobacterium smegmatis-pH 8.7, 30°C654527 2D-image
0.354-NAD+Mycobacterium smegmatis-pH 8.7, 30°C654527 2D-image

TURNOVER NUMBER [1/s] TURNOVER NUMBER MAXIMUM[1/s] SUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
additional information-additional informationMycobacterium smegmatis--654527-

kcat/KM VALUE [1/mMs-1]kcat/KM VALUE [1/mMs-1] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

Ki VALUE [mM]Ki VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

IC50 VALUE [mM]IC50 VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

SPECIFIC ACTIVITY [µmol/min/mg] SPECIFIC ACTIVITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
0.03-Amycolatopsis methanolica-cell free extract, in the absence of an unknown activating factor288324
0.08-Amycolatopsis methanolica-cell free extract, in the presence of an unknown activating factor288324
0.23-Amycolatopsis methanolica--288322
6.9-Amycolatopsis methanolica-substrate: ethanol288324
15-Amycolatopsis methanolica-substrate: formaldehyde288324
22.64-Mycobacterium smegmatis--654527

pH OPTIMUMpH MAXIMUMORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
89.5Mycobacterium smegmatis-optimal in Na-diphosphate buffer, buffers containing amino groups give poor activity, possibly because of Schiff base formation with formaldehyde654527
9-Amycolatopsis methanolica-formaldehyde as substrate288324
10.2-Amycolatopsis methanolica-alcohols as substrates288324

pH RANGEpH RANGE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

TEMPERATURE OPTIMUMTEMPERATURE OPTIMUM MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

TEMPERATURE RANGE TEMPERATURE MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pI VALUEpI VALUE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SOURCE TISSUE ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE SOURCE
cell cultureAmycolatopsis methanolica--288322, 288323Manually annotated by BRENDA team
cell cultureRhodococcus erythropolis--288322Manually annotated by BRENDA team
cell cultureAmycolatopsis methanolica-induction of enzyme and factor synthesis only if cells grown in methanol-containing medium288324Manually annotated by BRENDA team
cell cultureMycobacterium smegmatis--654527Manually annotated by BRENDA team

LOCALIZATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY GeneOntology No. LITERATURE SOURCE
No entries in this field

PDBSCOPCATHORGANISM
No entries in this field

MOLECULAR WEIGHT MOLECULAR WEIGHT MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
120000-Amycolatopsis methanolica-gel filtration288324

SUBUNITS ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
?Mycobacterium smegmatis-x * 38263, electrospray mass spectrometry654527
trimerAmycolatopsis methanolica-3 * 40000, SDS-PAGE288324

POSTTRANSLATIONAL MODIFICATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

Crystallization/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

pH STABILITYpH STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

TEMPERATURE STABILITYTEMPERATURE STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
No entries in this field

GENERAL STABILITYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

ORGANIC SOLVENT ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

OXIDATION STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

STORAGE STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

Purification/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-Amycolatopsis methanolica-288323
to homogeneityAmycolatopsis methanolica-288324
-Mycobacterium smegmatis-654527

Cloned/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

EXPRESSION ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

ENGINEERINGORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

Renatured/COMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

APPLICATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
additional informationNocardia sp.-thiol formation and detection of MSH-dependent formaldehyde dehydrogenase activity in cell extracts are relevant to the possible modulation of nitric oxide toxicity generated by strain NRRL 5646690518

REF. AUTHORS TITLE JOURNAL VOL. PAGES YEAR ORGANISMLINK TO PUBMEDSOURCE
288322Misset-Smits, M.; van Ophem, P.W.; Sakuda, S.; Duine, J.A.Mycothiol, 1-O-(2'-[N-acwtyl-L-cysteinyl]amido-2'-deoxy-alpha-D-glucopyranosyl)-D-myo-inositol, is the factor of NAD/factor-dependent formaldehyde dehydrogenaseFEBS Lett.409221-2221997Amycolatopsis methanolica, Rhodococcus erythropolis PubMed
288323Norin, A.; van Ophem, P.W.; Piersma, S.R.; Persson, B.; Duine, J.A.; Jörnvall, H.Mycothiol-dependent formaldehyde dehydrogenase, a prokaryotic medium-chain dehydrogenase/reductase, phylogenetically links different eukaroytic alcohol dehydrogenases. Primary structure, conformational modelling and functional correlationsEur. J. Biochem.248282-2891997Amycolatopsis methanolica PubMed
288324Van Ophem, P.W.; Van Beeumen, J.; Duine, J.A.NAD-linked, factor-dependent formaldehyde dehydrogenase or trimeric, zinc-containing, long-chain alcohol dehydrogenase from Amycolatopsis methanolicaEur. J. Biochem.206511-5181992Amycolatopsis methanolica PubMed
654527Vogt, R.N.; Steenkamp, D.J.; Zheng, R.; Blanchard, J.S.The metabolism of nitrosothiols in the Mycobacteria: identification and characterization of S-nitrosomycothiol reductaseBiochem. J.374657-6662003Mycobacterium smegmatis PubMed
690518Lee, S.; Bergeron, H.; Lau, P.C.; Rosazza, J.P.Thiols in nitric oxide synthase-containing Nocardia sp. strain NRRL 5646Appl. Environ. Microbiol.733095-30972007Nocardia sp. PubMed

LINKS TO OTHER DATABASES (specific for EC-Number 1.1.1.306)
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MetaCyc
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
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