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4.1.2.19: rhamnulose-1-phosphate aldolase

This is an abbreviated version!
For detailed information about rhamnulose-1-phosphate aldolase, go to the full flat file.

Word Map on EC 4.1.2.19

Reaction

L-rhamnulose 1-phosphate
=
glycerone phosphate
 +
(S)-lactaldehyde

Synonyms

aldolase, rhamnulose phosphate, L-Rhamnulose-1-phosphate aldolase, L-rhamnulose-1-phosphate aldolase (class II), L-Rhamnulose-1-phosphate L-lactaldehyde-lyase, Rha-1PA, RhaD, Rhamn-1PA, rhamnulose 1-phosphate aldolase, Rhamnulose phosphate aldolase, rhamnulose-1-phosphate aldolase, RhuA, TM1072

ECTree

     4 Lyases
         4.1 Carbon-carbon lyases
             4.1.2 Aldehyde-lyases
                4.1.2.19 rhamnulose-1-phosphate aldolase

Substrates Products

Substrates Products on EC 4.1.2.19 - rhamnulose-1-phosphate aldolase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2R)-2,3-dihydroxy-4-nitrobutanal
(1R,2R,3S,4R,5S,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol + (1S,2R,3R,4R,5R,6R)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol
show the reaction diagram
-
-
-
-
r
(2S)-2,3-dihydroxy-4-nitrobutanal
(1R,2R,3S,4S,5S,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol + 1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol
show the reaction diagram
-
-
-
-
r
(2S,3S)-3-methyl-1-oxopentane-2-benzylcarbamate
(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
show the reaction diagram
-
product ratio 55:45
-
?
(benzyloxy)acetaldehyde + dihydroxyacetone
(3R,4S)-5-(benzyloxy)-1,3,4-trihydroxypentan-2-one + (3R,4R)-5-(benzyloxy)-1,3,4-trihydroxypentan-2-one
show the reaction diagram
favored direction of reaction
-
-
r
(R)-1-oxobutane-2-benzylcarbamate
(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
show the reaction diagram
-
product ratio 48:30:11:11
-
?
(R)-1-oxohexane-2-benzylcarbamate
(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
show the reaction diagram
-
product ratio 28:63:5:5
-
?
(R)-1-oxopentane-2-benzylcarbamate
(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
show the reaction diagram
-
product ratio 44:34:11:10
-
?
(R)-3-methyl-1-oxobutane-2-benzylcarbamate
(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-isopropyl-3,4-diol
show the reaction diagram
-
-
-
?
(R)-4-methyl-1-oxopentane-2-benzylcarbamate
(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
show the reaction diagram
-
product ratio 32:43:16.9
-
?
(S)-1-oxo-3-phenylpropan-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-benzyl-3,4-diol
show the reaction diagram
-
-
-
?
(S)-1-oxobutane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol
show the reaction diagram
-
-
-
?
(S)-1-oxohexane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-butyl-3,4-diol + (2S,3S,4R,5S)-2-(hydroxymethyl)pyrrolidine-5-butyl-3,4-diol
show the reaction diagram
-
product ratio 93:7
-
?
(S)-1-oxopentane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol
show the reaction diagram
-
-
-
?
(S)-3-methyl-1-oxobutane-2-benzylcarbamate
(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
show the reaction diagram
-
product ratio 84:16
-
?
(S)-4-methyl-1-oxopentane-2-benzylcarbamate
(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
show the reaction diagram
-
product ratio 71:6:23
-
?
2 glycerone phosphate + 2 D-glyceraldehyde
D-psicose 1-phosphate + D-sorbose 1-phosphate
show the reaction diagram
-
-
-
?
2 glycerone phosphate + 2 L-glyceraldehyde
L-fructose 1-phosphate + L-tagatose 1-phosphate
show the reaction diagram
-
-
-
?
2-methyl-1-oxopropane-2-benzylcarbamate
(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-5-dimethyl-3,4-diol + (2R,3S,4R)-2-(hydroxymethyl)pyrrolidine-5-dimethyl-3,4-diol
show the reaction diagram
-
product ratio 44:56
-
?
3-hydroxy-4-nitrobutanal
(1R,2R,3S,5R,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,5-tetraol + (1S,2R,3R,5S,6R)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,5-tetraol
show the reaction diagram
-
-
-
-
r
4-nitrobutanal
(1R,2R,3S,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3-triol + (1S,2R,3R,6R)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3-triol
show the reaction diagram
-
-
-
-
?
6-Deoxy-L-sorbose 1-phosphate
Glycerone phosphate + D-lactaldehyde
show the reaction diagram
-
0.8% of the activity with L-rhamnulose 1-phosphate
-
-
?
benzyl (2-oxoethyl)carbamate + dihydroxyacetone
benzyl [(2S,3R)-2,3,5-trihydroxy-4-oxopentyl]carbamate + benzyl [(2R,3R)-2,3,5-trihydroxy-4-oxopentyl]carbamate
show the reaction diagram
favored direction of reaction
-
-
r
benzyl [(2R)-1-oxopropan-2-yl]carbamate + dihydroxyacetone
benzyl [(2R,3S,4R)-3,4,6-trihydroxy-5-oxohexan-2-yl]carbamate + benzyl [(2R,3R,4R)-3,4,6-trihydroxy-5-oxohexan-2-yl]carbamate
show the reaction diagram
favored direction of reaction
-
-
r
D-Fructose 1-phosphate
?
show the reaction diagram
-
1.7% of the activity with L-rhanmnulose 1-phosphate
-
-
?
D-Fructose-1,6-diphosphate
?
show the reaction diagram
-
1.8% of the activity with L-rhanmnulose 1-phosphate
-
-
?
D-Ribulose 1,5-diphosphate
?
show the reaction diagram
-
1.3% of the activity with L-rhanmnulose 1-phosphate
-
-
?
dihydroxyacetone + L-lactaldehyde
L-rhamnulose 1-phosphate
show the reaction diagram
favored direction of reaction
-
-
r
dihydroxyacetone phosphate + L-lactaldehyde
?
show the reaction diagram
-
-
-
?
dihydroxyacetone phosphate + L-lactaldehyde
L-rhamnulose 1-phosphate
show the reaction diagram
dihydroxyacetone phosphate + N-Cbz-(2R)-2-amino-3-methylbutanal
N-Cbz-5-amino-1,3,4-trihydroxyoctan-2-one
show the reaction diagram
-
-
yield 93%, ratio of (3R,4S) to (3S,4R) product is 2:98
-
?
dihydroxyacetone phosphate + N-Cbz-(2S)-2-amino-3-methylbutanal
N-Cbz-5-amino-1,3,4-trihydroxyoctan-2-one
show the reaction diagram
-
-
yield 93%, ratio of (3R,4S) to (3S,4R) product is 98:2
-
?
dihydroxyacetone phosphate + N-Cbz-(2S)-2-aminobutanal
N-Cbz-5-amino-1,3,4-trihydroxyheptan-2-one
show the reaction diagram
-
-
yield 94%, ratio of (3R,4S) to (3S,4R) product is 98:2
-
?
dihydroxyacetone phosphate + N-Cbz-(2S)-2-aminopropanal
N-Cbz-5-amino-1,3,4-trihydroxyhexan-2-one
show the reaction diagram
-
-
yield 99%, ratio of (3R,4S) to (3S,4R) product is 98:2
-
?
dihydroxyacetone phosphate + N-Cbz-aminoacetaldehyde
N-Cbz-5-amino-1,3,4-trihydroxypentan-2-one
show the reaction diagram
-
yield 91%, ratio of (3R,4S) to (3S,4R) product is 94:6
yield 91%, ratio of (3R,4S) to (3S,4R) product is 94:6
-
?
dimethoxyacetaldehyde + glycerone phosphate
(3R,4R)-3,4-dihydroxy-5,5-dimethoxy-2-oxopentyl phosphate
show the reaction diagram
-
-
-
-
?
DL-glycerol 3-phosphate + D-glyceraldehyde
D-psicose + D-sorbose
show the reaction diagram
-
-
-
?
DL-glycerol 3-phosphate + L-glyceraldehyde
L-fructose + D-tagatose
show the reaction diagram
-
-
-
?
Glycerone phosphate + (S)-lactaldehyde
L-Rhamnulose 1-phosphate
show the reaction diagram
Glycerone phosphate + acetaldehyde
5-Deoxy-L-xylulose 1-phosphate
show the reaction diagram
glycerone phosphate + benzyloxyacetaldehyde
(3R,4S)-5-(benzyloxy)-3,4-dihydroxy-2-oxopentyl phosphate
show the reaction diagram
-
68% aldol formation at 45°C
-
-
?
glycerone phosphate + D-glyceraldehyde
D-psicose 1-phosphate
show the reaction diagram
-
-
-
?
glycerone phosphate + D-glyceraldehyde
D-sorbose 1-phosphate
show the reaction diagram
Glycerone phosphate + D-lactaldehyde
6-Deoxy-D-sorbose 1-phosphate
show the reaction diagram
glycerone phosphate + ethyl-3-methyl-4-oxocrotonate
(3R,4S,5E)-7-ethoxy-3,4-dihydroxy-5-methyl-2,7-dioxohept-5-en-1-yl phosphate
show the reaction diagram
-
87% aldol formation at 45°C
-
-
?
Glycerone phosphate + formaldehyde
D-Erythrulose 1-phosphate
show the reaction diagram
Glycerone phosphate + glycolaldehyde
L-Xylulose 1-phosphate
show the reaction diagram
glycerone phosphate + L-glyceraldehyde
L-fructose 1-phosphate
show the reaction diagram
-
-
-
?
glycerone phosphate + L-glyceraldehyde
L-tagatose 1-phosphate
show the reaction diagram
-
-
-
?
glycerone phosphate + phenylacetaldehyde
(3R,4S)-3,4-dihydroxy-2-oxo-5-phenylpentyl phosphate
show the reaction diagram
-
53% aldol formation at 45°C
-
-
?
L-Rhamnulose 1-phosphate
?
show the reaction diagram
L-rhamnulose 1-phosphate
dihydroxyacetone phosphate + L-lactaldehyde
show the reaction diagram
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
show the reaction diagram
L-Sorbose 1-phosphate
Glycerone phosphate + D-glyceraldehyde
show the reaction diagram
N-formylglycinal + dihydroxyacetone
N-[(2S,3R)-2,3,5-trihydroxy-4-oxopentyl]formamide + N-[(2R,3R)-2,3,5-trihydroxy-4-oxopentyl]formamide
show the reaction diagram
-
-
-
r
Xylulose 1-phosphate
Glycerone phosphate + glycoaldehyde
show the reaction diagram
additional information
?
-