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533-50-6

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533-50-6 Usage

Description

L-(+)-Erythrulose is the L-isomer of D-Erythrulose (E650145), a tetrose carbohydrate that is characterized by its clear light yellow liquid appearance. It is known for its unique properties and applications in various industries.

Uses

Used in Cosmetics Industry:
L-(+)-Erythrulose is used as a tanning agent for self-tanning cosmetics, particularly when combined with dihydroxyacetone. It provides a natural-looking tan without the need for exposure to the sun or artificial UV sources, thus offering a safer alternative for achieving a tanned appearance.
Used in Organic Synthesis:
L-(+)-Erythrulose serves as a source of chiral ethyl ketones, which are utilized in the aldo reaction within the field of organic synthesis. Its unique chemical properties make it a valuable component in the creation of various compounds and materials.

Check Digit Verification of cas no

The CAS Registry Mumber 533-50-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 3 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 533-50:
(5*5)+(4*3)+(3*3)+(2*5)+(1*0)=56
56 % 10 = 6
So 533-50-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m0/s1

533-50-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name L-erythrulose

1.2 Other means of identification

Product number -
Other names L-Glycero-2-tetrulose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:533-50-6 SDS

533-50-6Synthetic route

threitol
2319-57-5

threitol

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With [(neocuproine)Pd(OAc)]2(OTf)2; oxygen In water; acetonitrile at 25℃; for 20h; chemoselective reaction;86%
formaldehyd
50-00-0

formaldehyd

dihydroxyacetone
96-26-4

dihydroxyacetone

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With D-fructose-6-phosphate aldolase of Escherichia coli Ala129Ser mutant In water at 25℃; for 21h; pH=7.5;68%
With D-fructose-6-phosphate aldolase of Escherichia coli Ala129Ser mutant at 25℃; pH=7.5; Kinetics; trisethanolamine buffer;
D-Serine
312-84-5

D-Serine

Glycolaldehyde
141-46-8

Glycolaldehyde

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With magnesium(II) chloride hexahydrate; flavin adenine dinucleotide (FAD)-containing flavoenzyme from the yeast Rhodotorula gracilis; thiamine pyrophosphate; oxygen In water at 25℃; for 8h; pH=7; Enzymatic reaction;67%
With transketolase from geobacillus stearothermophilus; D-amino acid oxidase from Rhodotorula gracilis; thiamine diphosphate; magnesium chloride In water at 25℃; for 8h; pH=7; Enzymatic reaction;44%
3-hydroxy-2-oxopropionic acid
1113-60-6

3-hydroxy-2-oxopropionic acid

Glycolaldehyde
141-46-8

Glycolaldehyde

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With thiamine pyrophosphate; magnesium chloride; transketolase from spinach 0.1 M glycylglycine buffer, pH 7.5;60%
With sodium hydroxide; thiamine diphosphate; Lithium hydroxypyruvate; magnesium chloride In water 3-5 d, transketolase (EC 2.2.1.1) from yeast;60%
at 37℃; transketolase, thiamine pyrophosphate, MgCl2, glycylglycine buffer pH 7.6; other aldehydes;
With thiamine pyrophosphate; magnesium chloride; transketolase from spinach In water glycyl-glycine buffer 0,05 M (pH 7.5);
at 37℃; transketolase, thiamine pyrophosphate, MgCl2, glycylglycine buffer pH 7.6;
Glycolaldehyde
141-46-8

Glycolaldehyde

Lithium hydroxypyruvate
3369-79-7

Lithium hydroxypyruvate

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With sodium hydroxide; magnesium(II) chloride hexahydrate; thiamine diphosphate In water at 25℃; for 24h; pH=7; Enzymatic reaction; optical yield given as %ee; stereoselective reaction;60%
With thiamine diphosphate; sodium hydroxide; magnesium chloride In glycylglycine buffer at 25℃; for 0.5h; pH=7.5; Enzymatic reaction;56%
With magnesium(II) chloride hexahydrate; trans ketolase from Geobacillus stearothermophilus; thiamine diphosphate; sodium hydroxide In water at 50℃; for 0.333333h; pH=7.5; Enzymatic reaction; stereospecific reaction;44%
L-erythrofuranose
210230-62-9

L-erythrofuranose

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With glucose isomerase (EC 5.3.1.5); magnesium sulfate In water at 60℃; for 8h;39%
meso-erythritol
909878-64-4

meso-erythritol

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
durch Bact.gluconicum, Bact.xylinoides, Bact.orleanese, Bact.aceti (Hansen);
durch Acetobacter suboxydans;
durch Acetobacter xylinum (Sorbosebakterien);
Conditions
ConditionsYield
(microbiological transformation);
D-threo-[2,5]hexodiulosonic acid; calcium salt (2:1)
24940-63-4

D-threo-[2,5]hexodiulosonic acid; calcium salt (2:1)

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With calcium hydroxide
Glycolaldehyde
141-46-8

Glycolaldehyde

Lithium hydroxypyruvate
3369-79-7

Lithium hydroxypyruvate

B

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With hydrogenchloride; thiamine pyrophosphate; Tris buffer; magnesium chloride at 25℃; spinach transketolase; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With thiamine diphosphate; magnesium chloride pH=7; aq. buffer; Supercritical conditions; Enzymatic reaction; optical yield given as %ee;
Glycolaldehyde
141-46-8

Glycolaldehyde

Potassium; 2-carboxy-2-oxo-ethanolate

Potassium; 2-carboxy-2-oxo-ethanolate

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With sodium hydroxide; thiamine pyrophosphate; magnesium chloride for 24h; E. coli transketolase, bovine serum albumin; Yield given;
2-<(4S,5S)-4,5-bis-hydroxymethyl-2,2-dimethyl-<1,3>dioxolan-4-yloxy>-ethanol

2-<(4S,5S)-4,5-bis-hydroxymethyl-2,2-dimethyl-<1,3>dioxolan-4-yloxy>-ethanol

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With sulfuric acid
(S)-<(S)-4-(2-hydroxy-ethoxy>-2,2-dimethyl-<1,3>dioxolan-4-yl>-ethane-1,2-diol

(S)-<(S)-4-(2-hydroxy-ethoxy>-2,2-dimethyl-<1,3>dioxolan-4-yl>-ethane-1,2-diol

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With sulfuric acid
meso-erythritol
909878-64-4

meso-erythritol

A

ethanol
64-17-5

ethanol

B

L-erythrulose
533-50-6

L-erythrulose

C

carbon dioxide
124-38-9

carbon dioxide

D

cellulose

cellulose

Conditions
ConditionsYield
durch Acetobacter xylinum;
β-hydroxypyruvate
1927-27-1

β-hydroxypyruvate

Glycolaldehyde
141-46-8

Glycolaldehyde

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With thiamine diphosphate In phosphate buffer at 25℃; pH=7.0;
meso-erythritol
909878-64-4

meso-erythritol

B

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With C30H42N4O6Pd2(2+)*2CF3O3S(1-); p-benzoquinone In water; acetonitrile at 60℃; for 1.2h; Darkness; Overall yield = 61 %; Overall yield = 140 mg; chemoselective reaction;A n/a
B n/a
Glycolaldehyde
141-46-8

Glycolaldehyde

L-erythrulose
533-50-6

L-erythrulose

Conditions
ConditionsYield
With Saccharomyces cerevisiae transketolase; thiamine pyrophosphate; magnesium(II) In aq. phosphate buffer at 25℃; for 24h; pH=7; Equilibrium constant; Enzymatic reaction;
L-erythrulose
533-50-6

L-erythrulose

dihydroxyacetone phosphate disodium salt

dihydroxyacetone phosphate disodium salt

C7H13O10P(2-)

C7H13O10P(2-)

Conditions
ConditionsYield
With cobalt(II) chloride hexahydrate; rhamnulose-1-phosphate aldolase from Bacteroides thetaiotaomicron In water at 20℃; for 5h; pH=7.5; Inert atmosphere; stereoselective reaction;92%
L-erythrulose
533-50-6

L-erythrulose

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

potassium thioacyanate
333-20-0

potassium thioacyanate

A

ethyl 2-(6-hydroxy-2-thioxotetrahydro-1H-furo[2,3-d]imidazole-1-yl)acetate

ethyl 2-(6-hydroxy-2-thioxotetrahydro-1H-furo[2,3-d]imidazole-1-yl)acetate

B

ethyl 2-(4,5-bis(hydroxymethyl)-2-thioxo-1H-imidazole-1-yl)acetate

ethyl 2-(4,5-bis(hydroxymethyl)-2-thioxo-1H-imidazole-1-yl)acetate

Conditions
ConditionsYield
With acetic acid In water; acetonitrile at 60℃; for 16h;A 90%
B n/a
L-erythrulose
533-50-6

L-erythrulose

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

C36H44O4Si2

C36H44O4Si2

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;86%
L-erythrulose
533-50-6

L-erythrulose

benzylamine hydrochloride
3287-99-8, 39110-74-2

benzylamine hydrochloride

potassium thioacyanate
333-20-0

potassium thioacyanate

1-benzyl-6-hydroxytetrahydro-1H-furo[2,3-d]imidazole-2(5H)-thione

1-benzyl-6-hydroxytetrahydro-1H-furo[2,3-d]imidazole-2(5H)-thione

Conditions
ConditionsYield
With acetic acid In water; acetonitrile at 60℃; for 16h;85%
L-erythrulose
533-50-6

L-erythrulose

sodium pyruvate
113-24-6

sodium pyruvate

C7H12O7*H3N

C7H12O7*H3N

Conditions
ConditionsYield
With pyruvate aldolase A3SLS0 for 15h; Enzymatic reaction;85%
L-erythrulose
533-50-6

L-erythrulose

formamidine acetic acid
3473-63-0

formamidine acetic acid

4(5)-(L-glycerodiitol-1-yl)imidazole

4(5)-(L-glycerodiitol-1-yl)imidazole

Conditions
ConditionsYield
With ammonia at 75℃; under 40 Torr; for 15h; bomb;83%
L-erythrulose
533-50-6

L-erythrulose

potassium thioacyanate
333-20-0

potassium thioacyanate

(2,4-dichlorophenyl)methanamine hydrochloride
73728-66-2

(2,4-dichlorophenyl)methanamine hydrochloride

A

(3aS,6R,6aR)-1-(2,4-dichlorobenzyl)-6-hydroxytetrahydro-1H-furo[2,3-d]imidazole-2(5H)-thione

(3aS,6R,6aR)-1-(2,4-dichlorobenzyl)-6-hydroxytetrahydro-1H-furo[2,3-d]imidazole-2(5H)-thione

B

(R)-1-(2,4-dichlorobenzyl)-5-(1,2-dihydroxyethyl)-1H-imidazole-2(3H)-thione

(R)-1-(2,4-dichlorobenzyl)-5-(1,2-dihydroxyethyl)-1H-imidazole-2(3H)-thione

Conditions
ConditionsYield
With acetic acid In water; acetonitrile at 60℃; for 16h;A 83%
B n/a
L-erythrulose
533-50-6

L-erythrulose

acetone
67-64-1

acetone

3,4-O-isopropylidene-L-(S)-erythrulose
115114-86-8

3,4-O-isopropylidene-L-(S)-erythrulose

Conditions
ConditionsYield
With sodium sulfate; zinc(II) chloride In 1,4-dioxane; methanol for 15h; Ambient temperature;81%
With copper(II) sulfate at 28℃; for 12h;
With camphor-10-sulfonic acid for 12h; Ambient temperature;
L-erythrulose
533-50-6

L-erythrulose

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1,4-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-butan-2-one
677300-95-7

1,4-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-butan-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;70%
C19(13)CH33(2)H3N4O14SP2

C19(13)CH33(2)H3N4O14SP2

L-erythrulose
533-50-6

L-erythrulose

C21(13)CH37(2)H3N4O16SP2

C21(13)CH37(2)H3N4O16SP2

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; thiamine diphosphate; magnesium chloride; alcohol dehydrogenase In various solvent(s) at 25℃; for 10h; pH=7.5;65%
L-erythrulose
533-50-6

L-erythrulose

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride
39637-99-5, 20445-33-4

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

C14H15F3O6
1191924-79-4

C14H15F3O6

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 12h;63%
C20(13)CH35(2)H3N4O14SP2

C20(13)CH35(2)H3N4O14SP2

L-erythrulose
533-50-6

L-erythrulose

C22(13)CH39(2)H3N4O16SP2

C22(13)CH39(2)H3N4O16SP2

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; thiamine diphosphate; magnesium chloride; alcohol dehydrogenase In various solvent(s) at 25℃; pH=7.5;62%
L-erythrulose
533-50-6

L-erythrulose

A

methyl 2-hydroxy-4-methoxybutanoate
1361017-70-0

methyl 2-hydroxy-4-methoxybutanoate

B

3-hydroxyoxolan-2-one
19444-84-9

3-hydroxyoxolan-2-one

Conditions
ConditionsYield
With Sn-MCM-41 In methanol at 89.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;A 61%
B 7%
L-erythrulose
533-50-6

L-erythrulose

A

methyl 2-hydroxybut-3-enoate
5837-73-0

methyl 2-hydroxybut-3-enoate

B

methyl 2-hydroxy-4-methoxybutanoate
1361017-70-0

methyl 2-hydroxy-4-methoxybutanoate

C

3-hydroxyoxolan-2-one
19444-84-9

3-hydroxyoxolan-2-one

Conditions
ConditionsYield
With Sn-MCM-41 In methanol at 139.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;A 60%
B 10%
C 8%
With tin In methanol at 159.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;A 50%
B 18%
C 8%
L-erythrulose
533-50-6

L-erythrulose

A

methyl 2-hydroxybut-3-enoate
5837-73-0

methyl 2-hydroxybut-3-enoate

B

methyl 2-hydroxy-4-methoxybutanoate
1361017-70-0

methyl 2-hydroxy-4-methoxybutanoate

Conditions
ConditionsYield
With tin (IV) chloride pentahydrate In methanol at 159.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;A 7%
B 57%
L-erythrulose
533-50-6

L-erythrulose

methyl 2-hydroxy-4-methoxybutanoate
1361017-70-0

methyl 2-hydroxy-4-methoxybutanoate

Conditions
ConditionsYield
With Sn-SBA-15 In methanol at 89.84℃; under 15001.5 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;57%
L-erythrulose
533-50-6

L-erythrulose

(2S)-2-hydroxy-4-oxobutyl phosphate sodium salt

(2S)-2-hydroxy-4-oxobutyl phosphate sodium salt

4-deoxy-D-fructose 6-phosphate sodium salt

4-deoxy-D-fructose 6-phosphate sodium salt

Conditions
ConditionsYield
With thiamine pyrophosphate; 1,4-dihydronicotinamide adenine dinucleotide; sodium formate; transketolase In water for 24h; pH=7.5; Enzyme kinetics; Condensation; Enzymatic reaction;52%
With thiamine pyrophosphate; 1,4-dihydronicotinamide adenine dinucleotide; sodium formate; formate dehydrogenase; transketolase In water for 24h; pH=7.5; Condensation; Enzymatic reaction;52%
L-erythrulose
533-50-6

L-erythrulose

(R)-methoxytrifluoromethylphenylacetyl chloride
20445-33-4, 39637-99-5

(R)-methoxytrifluoromethylphenylacetyl chloride

C14H15F3O6
1191924-83-0

C14H15F3O6

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 12h;51%
L-erythrulose
533-50-6

L-erythrulose

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

acetone
67-64-1

acetone

3,4-O-isopropylidene-L-(S)-erythrulose
115114-86-8

3,4-O-isopropylidene-L-(S)-erythrulose

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 0.5h; Ambient temperature;50%
L-erythrulose
533-50-6

L-erythrulose

di-tert-butyl 2,2’-({[1R-(1α,2α,3α,4α,5α,6α)]-5-amino-2,4,6-tris[benzyloxy]cyclo-hexane-1,3-diyl}diimino)diacetate

di-tert-butyl 2,2’-({[1R-(1α,2α,3α,4α,5α,6α)]-5-amino-2,4,6-tris[benzyloxy]cyclo-hexane-1,3-diyl}diimino)diacetate

di-tert-butyl 2,2’-({[1R-(1α,2α,3α,4α,5α,6α)]-2,4,6-tris(benzyloxy)-5-[(1,3,4-trihydroxy-butan-2-yl)amino]cyclohexane-1,3-diyl}diimino)diacetate

di-tert-butyl 2,2’-({[1R-(1α,2α,3α,4α,5α,6α)]-2,4,6-tris(benzyloxy)-5-[(1,3,4-trihydroxy-butan-2-yl)amino]cyclohexane-1,3-diyl}diimino)diacetate

Conditions
ConditionsYield
With 5-ethyl-2-methylpyridine borane complex; acetic acid In methanol; toluene at 20℃; for 96h;31%
cyclopent-2-enone
930-30-3

cyclopent-2-enone

L-erythrulose
533-50-6

L-erythrulose

A

3-hydroxymethyl-tetrahydro-1,4-dioxa-cyclopenta[cd]pentalene-2a,4a-diol

3-hydroxymethyl-tetrahydro-1,4-dioxa-cyclopenta[cd]pentalene-2a,4a-diol

B

1,4-dihydroxy-3-hydroxymethyl-2,6-dioxatricyclo[5.2.1.04,10]decane

1,4-dihydroxy-3-hydroxymethyl-2,6-dioxatricyclo[5.2.1.04,10]decane

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃; for 18h;A 8%
B 30%
L-valine
72-18-4

L-valine

L-erythrulose
533-50-6

L-erythrulose

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

A

(3R,5S)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

(3R,5S)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

B

(2R,3R,5S)-N-(tert-butyl)-2,3-bis(hydroxymethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

(2R,3R,5S)-N-(tert-butyl)-2,3-bis(hydroxymethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

C

(3S,5R,6R)-N-(tert-butyl)-6-hydroxy-5-(hydroxymethyl)-3-isopropyl-2-oxo-1,4-oxazepane-5-carboxamide

(3S,5R,6R)-N-(tert-butyl)-6-hydroxy-5-(hydroxymethyl)-3-isopropyl-2-oxo-1,4-oxazepane-5-carboxamide

Conditions
ConditionsYield
With trifluoroethanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 16h; Overall yield = 62 %; Overall yield = 130.6 mg; stereoselective reaction;A 30%
B 21%
C 11%
Wilkinson's catalyst
14694-95-2

Wilkinson's catalyst

L-erythrulose
533-50-6

L-erythrulose

A

ethanol
64-17-5

ethanol

B

meso-erythritol
909878-64-4

meso-erythritol

rac-threitol
6968-16-7

rac-threitol

E

glycerol
56-81-5

glycerol

Conditions
ConditionsYield
In N,N-dimethyl acetamide argon-filled glovebox, durene, bibenzyl, heating 23h, further products; detn. of products by GC;A 10%
B 1-2
C 1-2
D 1-2
E 24%
D-Val-OH
640-68-6

D-Val-OH

L-erythrulose
533-50-6

L-erythrulose

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

A

(3S,5R)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

(3S,5R)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

B

(3R,5R)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

(3R,5R)-N-(tert-butyl)-3-((R)-1,2-dihydroxyethyl)-5-isopropyl-6-oxomorpholine-3-carboxamide

Conditions
ConditionsYield
With trifluoroethanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 16h; Overall yield = 38 %; stereoselective reaction;A 24%
B 14%

533-50-6Relevant articles and documents

Microfluidic multi-input reactor for biocatalytic synthesis using transketolase

Lawrence, James,O'Sullivan, Brian,Lye, Gary J.,Wohlgemuth, Roland,Szita, Nicolas

, p. 111 - 117 (2013)

Biocatalytic synthesis in continuous-flow microreactors is of increasing interest for the production of specialty chemicals. However, the yield of production achievable in these reactors can be limited by the adverse effects of high substrate concentration on the biocatalyst, including inhibition and denaturation. Fed-batch reactors have been developed in order to overcome this problem, but no continuous-flow solution exists. We present the design of a novel multi-input microfluidic reactor, capable of substrate feeding at multiple points, as a first step towards overcoming these problems in a continuous-flow setting. Using the transketolase-(TK) catalysed reaction of lithium hydroxypyruvate (HPA) and glycolaldehyde (GA) to l-erythrulose (ERY), we demonstrate the transposition of a fed-batch substrate feeding strategy to our microfluidic reactor. We obtained a 4.5-fold increase in output concentration and a 5-fold increase in throughput compared with a single input reactor.

Enantioselective Reductive Oligomerization of Carbon Dioxide into l-Erythrulose via a Chemoenzymatic Catalysis

Bontemps, Sébastien,Clapés, Pere,Desmons, Sarah,Dumon, Claire,Fauré, Régis,Grayson-Steel, Katie,Hurtado, John,Nu?ez-Dallos, Nelson,Vendier, Laure

supporting information, p. 16274 - 16283 (2021/10/12)

A cell-free enantioselective transformation of the carbon atom of CO2has never been reported. In the urgent context of transforming CO2into products of high value, the enantiocontrolled synthesis of chiral compounds from CO2would be highly desirable. Using an original hybrid chemoenzymatic catalytic process, we report herein the reductive oligomerization of CO2into C3(dihydroxyacetone, DHA) and C4(l-erythrulose) carbohydrates, with perfect enantioselectivity of the latter chiral product. This was achieved with the key intermediacy of formaldehyde. CO2is first reduced selectively by 4e-by an iron-catalyzed hydroboration reaction, leading to the isolation and complete characterization of a new bis(boryl)acetal compound derived from dimesitylborane. In an aqueous buffer solution at 30 °C, this compound readily releases formaldehyde, which is then involved in selective enzymatic transformations, giving rise either (i) to DHA using a formolase (FLS) catalysis or (ii) to l-erythrulose with a cascade reaction combining FLS and d-fructose-6-phosphate aldolase (FSA) A129S variant. Finally, the nature of the synthesized products is noteworthy, since carbohydrates are of high interest for the chemical and pharmaceutical industries. The present results prove that the cell-freede novosynthesis of carbohydrates from CO2as a sustainable carbon source is a possible alternative pathway in addition to the intensely studied biomass extraction andde novosyntheses from fossil resources.

D -Serine as a Key Building Block: Enzymatic Process Development and Smart Applications within the Cascade Enzymatic Concept

Auffray, Pascal,Charmantray, Franck,Collin, Jér?me,Hecquet, Laurence,L'Enfant, Mélanie,Martin, Juliette,Ocal, Nazim,Pollegioni, Loredano

, p. 769 - 775 (2020/07/14)

An efficient enzymatic method catalyzed by an enzyme from the d-threonine aldolase (DTA) family was developed for d-serine production at industrial scale. This process was used for the synthesis of two valuable ketoses, l-erythrulose and d-fructose, within the cascade enzymatic concept involving two other enzymes. Indeed, d-serine was used as a substrate of d-amino acid oxidase (DAAO) for the in situ generation of the corresponding α-keto acid, hydroxypyruvic acid (HPA), a key donor substrate of transketolase (TK). This enzyme catalyzed the irreversible transfer of the ketol group from HPA to an aldehyde acceptor to form a (3S)-ketose by stereoselective carbon-carbon bond formation. The compatibility of all enzymes and substrates allowed a sequential three-step enzymatic process to be performed without purification of the intermediates. This strategy was validated with two TK aldehyde substrates to finally obtain the corresponding (3S)-ketoses with high control of the stereoselectivity and excellent aldehyde conversion rates.

Separating Thermodynamics from Kinetics—A New Understanding of the Transketolase Reaction

Marsden, Stefan R.,Gjonaj, Lorina,Eustace, Stephen J.,Hanefeld, Ulf

, p. 1808 - 1814 (2017/05/26)

Transketolase catalyzes asymmetric C?C bond formation of two highly polar compounds. Over the last 30 years, the reaction has unanimously been described in literature as irreversible because of the concomitant release of CO2 if using lithium hydroxypyruvate (LiHPA) as a substrate. Following the reaction over a longer period of time however, we have now found it to be initially kinetically controlled. Contrary to previous suggestions, for the non-natural conversion of synthetically more interesting apolar substrates, the complete change of active-site polarity is therefore not necessary. From docking studies it was revealed that water and hydrogen-bond networks are essential for substrate binding, thus allowing aliphatic aldehydes to be converted in the charged active site of transketolase.

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