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Information on EC 1.1.1.B18 - L-1-amino-2-propanol dehydrogenase
for references in articles please use BRENDA:EC1.1.1.B18
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preliminary BRENDA-supplied EC number
EC Tree 1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.1.1 With NAD+ or NADP+ as acceptor
1.1.1.B18 L-1-amino-2-propanol dehydrogenase
The expected taxonomic range for this enzyme is: Rhodococcus erythropolis
Reaction Schemes
showSynonyms
l-1-amino-2-propanol dehydrogenase, nadp+-dependent aminoalcohol dehydrogenase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
AADH
amino alcohol dehydrogenase
L-1-amino-2-propanol dehydrogenase
NADP+-dependent aminoalcohol dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+ = (2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
redox reaction
reduction
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SYSTEMATIC NAME
IUBMB Comments
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol:NADP+ 1-oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY
1262091-13-3
-
1262091-13-3
UniProt-ID D6MMN3
283594-89-8
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283594-89-9
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: -
Products: -
r
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: conversion with with more than 99% enantiomeric excess, 78% yield and a productivity of 3.9 mmol(S)-phenylepinephrine/l h in 12 h at 30°C and pH 7
Products: conversion with with more than 99% enantiomeric excess, 78% yield and a productivity of 3.9 mmol(S)-phenylepinephrine/l h in 12 h at 30°C and pH 7
?
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: i.e. D-pseudoephedrine
Products: i.e. D-pseudoephedrine
?
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: diastereoselective reduction
Products: i.e. d-psi-pseudoephedrine, molar reaction yields of 89.1% and more than 99% enantiomeric and diastereomeric excess
Products: i.e. d-psi-pseudoephedrine, molar reaction yields of 89.1% and more than 99% enantiomeric and diastereomeric excess
?
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: conversion with with more than 99% enantiomeric excess, 78% yield and a productivity of 3.9 mmol(S)-phenylepinephrine/l h in 12 h at 30°C and pH 7
Products: conversion with with more than 99% enantiomeric excess, 78% yield and a productivity of 3.9 mmol(S)-phenylepinephrine/l h in 12 h at 30°C and pH 7
?
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: i.e. D-pseudoephedrine
Products: i.e. D-pseudoephedrine
?
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: -
Products: -
r
DL-1-amino-2-butanol + NADPH + H+
? + NADP+
Substrates: 95% of the activity with L-1-amino-2-propanol
Products: -
Products: -
?
DL-1-amino-2-butanol + NADPH + H+
? + NADP+
Substrates: 95% of the activity with L-1-amino-2-propanol
Products: -
Products: -
?
DL-2-aminocyclohexanol + NADPH + H+
? + NADP+
Substrates: 50% of the activity with L-1-amino-2-propanol
Products: -
Products: -
?
DL-2-aminocyclohexanol + NADPH + H+
? + NADP+
Substrates: 50% of the activity with L-1-amino-2-propanol
Products: -
Products: -
?
L-1-amino-2-propanol + NADPH + H+
? + NADP+
Substrates: best substrate
Products: -
Products: -
?
L-1-amino-2-propanol + NADPH + H+
? + NADP+
Substrates: best substrate
Products: -
Products: -
?
additional information
?
-
Substrates: no substrate: D-1-amino-2-propanol, 2-aminoethanol, 2-bromoethanol, 2-buten-1-ol, 2-propen-1-ol, 2-phenylethanol, 3-phenyl-1-propanol, 2,5-hexanediol, trimethyleneglycol, 1-nonanol, 1-decanol, 1-dodecanol, 2-butanol, 1,3-butanediol and 1,4-butanediol
Products: -
Products: -
?
additional information
?
-
-
Substrates: no substrate: D-1-amino-2-propanol, 2-aminoethanol, 2-bromoethanol, 2-buten-1-ol, 2-propen-1-ol, 2-phenylethanol, 3-phenyl-1-propanol, 2,5-hexanediol, trimethyleneglycol, 1-nonanol, 1-decanol, 1-dodecanol, 2-butanol, 1,3-butanediol and 1,4-butanediol
Products: -
Products: -
?
additional information
?
-
Substrates: no substrate: D-1-amino-2-propanol, 2-aminoethanol, 2-bromoethanol, 2-buten-1-ol, 2-propen-1-ol, 2-phenylethanol, 3-phenyl-1-propanol, 2,5-hexanediol, trimethyleneglycol, 1-nonanol, 1-decanol, 1-dodecanol, 2-butanol, 1,3-butanediol and 1,4-butanediol
Products: -
Products: -
?
additional information
?
-
-
Substrates: no substrate: D-1-amino-2-propanol, 2-aminoethanol, 2-bromoethanol, 2-buten-1-ol, 2-propen-1-ol, 2-phenylethanol, 3-phenyl-1-propanol, 2,5-hexanediol, trimethyleneglycol, 1-nonanol, 1-decanol, 1-dodecanol, 2-butanol, 1,3-butanediol and 1,4-butanediol
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: i.e. D-pseudoephedrine
Products: i.e. D-pseudoephedrine
?
(2S)-2-(methylamino)-1-phenylpropan-1-one + NADPH + H+
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol + NADP+
Substrates: -
Products: i.e. D-pseudoephedrine
Products: i.e. D-pseudoephedrine
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
product inhibition above 20 mg/ml
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
additional information
metabolism
the enzyme participates in aminoalcohol or aminoketone metabolism in the organism
metabolism
-
the enzyme participates in aminoalcohol or aminoketone metabolism in the organism
-
additional information
OrfE is a negative regulator that represses gene aadh expression in the absence of 1-amino-2-propanol, analysis of enzyme regulation in tan OrfE-deficient mutant, overview
additional information
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OrfE is a negative regulator that represses gene aadh expression in the absence of 1-amino-2-propanol, analysis of enzyme regulation in tan OrfE-deficient mutant, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
26580
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
tetramer
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
OrfE is a negative regulator that represses gene aadh expression in the absence of 1-amino-2-propanol. Construction of orfE disruption mutant and analysis of enzyme regulation in an OrfE-deficient mutant, overview
additional information
-
OrfE is a negative regulator that represses gene aadh expression in the absence of 1-amino-2-propanol. Construction of orfE disruption mutant and analysis of enzyme regulation in an OrfE-deficient mutant, overview
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
construction of Rhodococcus expression vectors, derived from the Rhodococcus/Escherichia coli shuttle vector pRET1102, to express aadh. The plasmid pRET1102 can be transformed into many actinomycete strains, including Rhodococcus erythropolis. The transformation efficiency for a species closely related to Rhodococcus erythropolis is higher than that for other actinomycete strains. Promoters of various strengths, hsp, 1200rep, and TRR, are obtained from Gram-positive bacteria. The activity of TRR is stronger than that of hsp and 1200rep. The aadh-expressing plasmid pRET1172 with TRR can be transformed into many actinomycete strains to increase their AADH production. The Rhodococcus expression vector, pRET11100, constructed by removing aadh from the pRET1172 plasmid may be useful for bioconversion
gene aadh, DNA and amino acid sequence determination and analysis, expression analysis
gene aadh, DNA and amino acid sequence determination and analysis, expression in Escherichia coli JM109 leading to a 10.4fold increase in specific activity as to catalysis of the reduction of (2S)-2-(methylamino)-1-phenylpropan-1-one, as compared with that of Rhodococcus erythropolis strain MAK154 induced by 1-amino-2-propanol. Coexpression of aadh with glucose dehydrogenase gene gdh as cofactor regeneration enzyme, and installation of a system for sufficient production of d-psi-pseudoephedrine from racemic (S)-1-phenyl-2-methylaminopropan-1-one
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is induced on cultivation with aminoalcohols such as 1-amino-2-propanol, 1-amino-2-butanol and 2-aminocyclohexanol
OrfE is a negative regulator that represses gene aadh expression in the absence of 1-amino-2-propanol
the enzyme is induced by the addition of several aminoalcohols, such as 1-amino-2-propanol
expression is induced on cultivation with aminoalcohols such as 1-amino-2-propanol, 1-amino-2-butanol and 2-aminocyclohexanol
expression is induced on cultivation with aminoalcohols such as 1-amino-2-propanol, 1-amino-2-butanol and 2-aminocyclohexanol
-
-
OrfE is a negative regulator that represses gene aadh expression in the absence of 1-amino-2-propanol
OrfE is a negative regulator that represses gene aadh expression in the absence of 1-amino-2-propanol
-
-
the enzyme is induced by the addition of several aminoalcohols, such as 1-amino-2-propanol
the enzyme is induced by the addition of several aminoalcohols, such as 1-amino-2-propanol
-
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pharmacology
synthesis
pharmacology
the enzyme produces double chiral aminoalcohols, which are used as pharmaceuticals. The Rhodococcus expression vector, pRET11100, constructed by removing aadh from the pRET1172 plasmid may be useful for bioconversion
pharmacology
-
the enzyme produces double chiral aminoalcohols, which are used as pharmaceuticals. The Rhodococcus expression vector, pRET11100, constructed by removing aadh from the pRET1172 plasmid may be useful for bioconversion
-
synthesis
coversion of 1-(3-hydroxyphenyl)-2-(methylamino) ethanone to (S)-phenylephrine with with more than 99% enantiomeric excess, 78% yield and a productivity of 3.9 mmol(S)-phenylepinephrine/l h in 12 h at 30°C and pH 7. The (S)-phenylepinephrine, recovered from reaction mixture by precipitation at pH 11.3, can be converted to (R)-phenylepinephrine by Walden inversion reaction
synthesis
-
coversion of 1-(3-hydroxyphenyl)-2-(methylamino) ethanone to (S)-phenylephrine with with more than 99% enantiomeric excess, 78% yield and a productivity of 3.9 mmol(S)-phenylepinephrine/l h in 12 h at 30°C and pH 7. The (S)-phenylepinephrine, recovered from reaction mixture by precipitation at pH 11.3, can be converted to (R)-phenylepinephrine by Walden inversion reaction
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kataoka, M.; Ishige, T.; Urano, N.; Nakamura, Y.; Sakuradani, E.; Fukui, S.; Kita, S.; Sakamoto, K.; Shimizu, S.
Cloning and expression of the L-1-amino-2-propanol dehydrogenase gene from Rhodococcus erythropolis, and its application to double chiral compound production
Appl. Microbiol. Biotechnol.
80
597-604
2008
Rhodococcus erythropolis (A1IG83)
brenda
Kataoka, M.; Nakamura, Y.; Urano, N.; Ishige, T.; Shi, G.; Kita, S.; Sakamoto, K.; Shimizu, S.
A novel NADP+-dependent L-1-amino-2-propanol dehydrogenase from Rhodococcus erythropolis MAK154: a promising enzyme for the production of double chiral aminoalcohols
Lett. Appl. Microbiol.
43
430-455
2006
Rhodococcus erythropolis (A1IG83), Rhodococcus erythropolis, Rhodococcus erythropolis MAK154 (A1IG83), Rhodococcus erythropolis MAK154
brenda
Lin, W.; Chen, C.; Chen, H.; Hsu, W.
Enantioselective synthesis of (S)-phenylephrine by whole cells of recombinant Escherichia coli expressing the amino alcohol dehydrogenase gene from Rhodococcus erythropolis BCRC 10909
Process Biochem.
45
1529-1536
2010
Rhodococcus erythropolis (D6MMN3), Rhodococcus erythropolis BCRC 10909 (D6MMN3)
-
brenda
Urano, N.; Kataoka, M.; Ishige, T.; Kita, S.; Sakamoto, K.; Shimizu, S.
Genetic analysis around aminoalcohol dehydrogenase gene of Rhodococcus erythropolis MAK154: a putative GntR transcription factor in transcriptional regulation
Appl. Microbiol. Biotechnol.
89
739-746
2011
Rhodococcus erythropolis (A1IG83), Rhodococcus erythropolis MAK154 (A1IG83)
brenda
Yamamura, E.T.
Construction of Rhodococcus expression vectors and expression of the aminoalcohol dehydrogenase gene in Rhodococcus erythropolis
Biosci. Biotechnol. Biochem.
82
1396-1403
2018
Rhodococcus erythropolis (A1IG83), Rhodococcus erythropolis, Rhodococcus erythropolis MAK154 (A1IG83), Rhodococcus erythropolis MAK154
brenda
EXTERNAL LINKS (specific for EC-Number 1.1.1.B18)
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Release 2023.1 (January 2023)
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