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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.

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  • 533-50-6 Structure
  • Basic information

    1. Product Name: L-(+)-Erythrulose
    2. Synonyms: L-(+)-Erythrulose;(3S)-1,3,4-trihydroxybutan-2-one;L-(+)-erythrulose hydrate;(3S)-1,3,4-Trihydroxy-2-butanone;(S)-1,3,4-Trihydroxy-2-butanone;L-glycero-2-Tetrulose;C02045;L-Glycero-tetrulose
    3. CAS NO:533-50-6
    4. Molecular Formula: C4H8O4
    5. Molecular Weight: 120.10392
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 533-50-6.mol
    9. Article Data: 33
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 144.07°C (rough estimate)
    3. Flash Point: 110℃
    4. Appearance: /
    5. Density: 1.420
    6. Vapor Pressure: 2.8E-06mmHg at 25°C
    7. Refractive Index: 1.4502 (estimate)
    8. Storage Temp.: room temp
    9. Solubility: Methanol (Slightly), Water (Slightly)
    10. PKA: 12.00±0.20(Predicted)
    11. Stability: Hygroscopic
    12. CAS DataBase Reference: L-(+)-Erythrulose(CAS DataBase Reference)
    13. NIST Chemistry Reference: L-(+)-Erythrulose(533-50-6)
    14. EPA Substance Registry System: L-(+)-Erythrulose(533-50-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 533-50-6(Hazardous Substances Data)

533-50-6 Usage

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.

L-erythrulose production by oxidative fermentation is catalyzed by PQQ-containing membrane-bound dehydrogenase.

Moonmangmee, Duangtip,Adachi, Osao,Shinagawa, Emiko,Toyama, Hirohide,Theeragool, Gunjana,Lotong, Napha,Matsushita, Kazunobu

, p. 307 - 318 (2002)

Thermotolerant Gluconobacter frateurii CHM 43 was selected for L-erythrulose production from mesoerythritol at higher temperatures. Growing cells and the membrane fraction of the strain rapidly oxidized mesoerythritol to L-erythrulose irreversibly with almost 100% of recovery at 37 degrees C. L-Erythrulose was also produced efficiently by the resting cells at 37 degrees C with 85% recovery. The enzyme responsible for mesoerythritol oxidation was found to be located in the cytoplasmic membrane of the organism. The EDTA-resolved enzyme required PQQ and Ca2+ for L-erythrulose formation, suggesting that the enzyme catalyzing meso-erythritol oxidation was a quinoprotein. Quinoprotein membrane-bound mesoerythritol dehydrogenase (QMEDH) was solubilized and purified to homogeneity. The purified enzyme showed a single band in SDS-PAGE of which the molecular mass corresponded to 80 kDa. The optimum pH of QMEDH was found at pH 5.0. The Michaelis constant of the enzyme was found to be 25 mM for meso-erythritol as the substrate. QMEDH showed a broad substrate specificity toward C3-C6 sugar alcohols in which the erythro form of two hydroxy groups existed adjacent to a primary alcohol group. On the other hand, the cytosolic NAD-denpendent meso-erythritol dehydrogenase (CMEDH) of the same organism was purified to a crystalline state. CMEDH showed a molecular mass of 60 kDa composed of two identical subunits, and an apparent sedimentation constant was 3.6 s. CMEDH catalyzed oxidoreduction between mesoerythritol and L-erythrulose. The oxidation reaction was observed to be reversible in the presence of NAD at alkaline pHs such as 9.0-10.5. L-Erythrulose reduction was found at pH 6.0 with NADH as coenzyme. Judging from the catalytic properties, the NAD-dependent enzyme in the cytosolic fraction was regarded as a typical pentitol dehydrogenase of NAD-dependent and the enzyme was independent of the oxidative fermentation of L-erythrulose production.

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.

PROCESSES FOR PREPARING C-4 SUGARS AND KETOSE SUGARS

-

Page/Page column 37-39, (2021/11/20)

Various processes for preparing C4 aldoses and/or ketones thereof are described. Various processes are described for preparing C4 aldoses and/or ketones thereof from feed compositions comprising glycolaldehyde. Also, various processes for preparing useful downstream products and intermediates, such as erythritol and erythronic acid, from the C4 aldoses and/or ketones thereof are described.

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.

One-Pot Cascade Synthesis of (3S)-Hydroxyketones Catalyzed by Transketolase via Hydroxypyruvate Generated in Situ from d-Serine by d-Amino Acid Oxidase

L'enfant, Mélanie,Bruna, Felipe,Lorillière, Marion,Ocal, Nazim,Fessner, Wolf-Dieter,Pollegioni, Loredano,Charmantray, Franck,Hecquet, Laurence

, p. 2550 - 2558 (2019/04/17)

We described an efficient in situ generation of hydroxypyruvate from d-serine catalyzed by a d-amino acid oxidase from Rhodotorula gracilis. This strategy revealed an interesting alternative to the conventional chemical synthesis of hydroxypyruvate starting from toxic bromopyruvate or to the enzymatic transamination from l-serine requiring an additional substrate as amino acceptor. Hydroxypyruvate thus produced was used as donor substrate of transketolases from Escherichia coli or from Geobacillus stearothermophilus catalyzing the stereoselective formation of a carbon?carbon bond. The enzymatic cascade reaction was performed in one-pot in the presence of d-serine and appropriate aldehydes for the synthesis of valuable (3S)-hydroxyketones, which were obtained with high enantio- and diastereoselectivity and in good yield. The efficiency of the process was based on the irreversibility of both reactions allowing complete conversion of d-serine and aldehydes. (Figure presented.).

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.

Efficient Production of Biomass-Derived C4 Chiral Synthons in Aqueous Solution

Lin, Shaoying,Guo, Xiao,Qin, Kai,Feng, Lei,Zhang, Yahong,Tang, Yi

, p. 4179 - 4184 (2017/12/02)

Carbohydrates are expected to replace petroleum and to become the base of industrial chemistry. Chirality is one particular area in which carbohydrates have a special potential advantage over petroleum resources. Herein, we report a catalytic approach for the direct production of d-tetroses [i.e., d-(?)-erythrose and d-(+)-erythrulose] from d-hexoses through a fast retro-aldol process at 190 °C that achieves a yield of 46 % and completely retains the chiral centers in the final chiral synthon. The d-tetrose products were further converted into their derivatives, thereby accomplishing transfer of chirality from natural chiral hexoses to high-value-added chiral chemicals. Our results also suggest that the product distribution for the conversion of d-hexoses was determined by their isomerization and epimerization trends that competed with their corresponding retro-aldol condensation processes.

ISOMERISATION OF C4-C6 ALDOSES WITH ZEOLITES

-

Page/Page column 25-28, (2014/03/25)

The present invention relates to isomerization of C4-C6 aldoses to their corresponding C4-C6 ketoses. In particular, the invention concerns isomerization of C4-C6 aldoses over solid zeolite catalysts free of any metals other than aluminum, in the presence of suitable solvent(s) at suitable elevated temperatures. C6 and C5 aldose sugars such as glucose and xylose, which are available in large amounts from biomass precursors, are isomerized to fructose and xylulose respectively, in a one or two-step process over inexpensive commercially available zeolite catalysts, containing aluminum as the only metal in the catalyst. The ketoses obtained are used as sweeteners in the food and/or brewery industry, or treated to obtain downstream platform chemicals such as lactic acid, HMF, levulinic acid, furfural, MMHB, and the like. FIG. 7

Zeolite-catalyzed isomerization of tetroses in aqueous medium

Saravanamurugan, Shunmugavel,Riisager, Anders

, p. 3186 - 3190 (2014/08/18)

The isomerization of erythrose (ERO) was studied in water over commercially available large-pore zeolites, e.g. H-Y, H-USY and H-beta. Among the employed zeolites, H-USY(6) was found to efficiently isomerize the sugar, yielding 45% erythrulose (ERU), 42% ERO and 3% of the epimer threose (THO) (corresponding to the equilibrium mixture), i.e. total tetrose yield 90%, after reaction for 5-7 h at 120 °C. Changing the solvent from water to methanol decreased the yield of ERU markedly to 18% and gave only a total yield of tetroses of 27% which is significantly lower than that obtained in water. Hence, the results demonstrate that water is the preferred solvent compared to lower alcohols for zeolite-catalyzed tetrose isomerization, which is opposite to what has been found previously for analogous pentose and hexose isomerization. A reuse study revealed further that H-USY(6) could be applied for at least five reaction runs with essentially unchanged activity and without significant aluminum leaching from the catalyst. The use of benign reaction conditions and an industrially pertinent solid catalyst in combination with water establishes a new, green tetrose isomerization protocol. the Partner Organisations 2014.

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