Welcome to LookChem.com Sign In|Join Free

CAS

  • or

4042-36-8

Post Buying Request

4042-36-8 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

4042-36-8 Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 4042-36-8 differently. You can refer to the following data:
1. Serves as a building block in the synthesis of diphthamide
2. Serves as a building block in the synthesis of diphthamide.

Definition

ChEBI: The D-enantiomer of 5-oxoproline.

Purification Methods

Purify R-pyroglutamic acid by dissolving it in H2O, filtering, passing the filtrate through Dowex 50 (H+ form), washing with H2O, pooling washings, evaporating, removing H2O azeotropically with Me2CO and *C6H6, washing the residue with Et2O and recrystallising from EtOH/pet ether. [Pradeller et al. Collect Czech Chem Commun 42 79, 80 1977, Beilstein 22/6 V 7.]

Check Digit Verification of cas no

The CAS Registry Mumber 4042-36-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,4 and 2 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4042-36:
(6*4)+(5*0)+(4*4)+(3*2)+(2*3)+(1*6)=58
58 % 10 = 8
So 4042-36-8 is a valid CAS Registry Number.
InChI:InChI=1/C5H7NO3/c7-4-2-1-3-6(4)5(8)9/h1-3H2,(H,8,9)

4042-36-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (P1354)  D-Pyroglutamic Acid  >98.0%(T)

  • 4042-36-8

  • 5g

  • 430.00CNY

  • Detail
  • TCI America

  • (P1354)  D-Pyroglutamic Acid  >98.0%(T)

  • 4042-36-8

  • 25g

  • 1,330.00CNY

  • Detail
  • Alfa Aesar

  • (B24678)  (R)-(+)-2-Pyrrolidinone-5-carboxylic acid, 98+%   

  • 4042-36-8

  • 5g

  • 683.0CNY

  • Detail
  • Alfa Aesar

  • (B24678)  (R)-(+)-2-Pyrrolidinone-5-carboxylic acid, 98+%   

  • 4042-36-8

  • 25g

  • 1500.0CNY

  • Detail
  • Alfa Aesar

  • (B24678)  (R)-(+)-2-Pyrrolidinone-5-carboxylic acid, 98+%   

  • 4042-36-8

  • 100g

  • 5584.0CNY

  • Detail
  • Aldrich

  • (422614)  (R)-(+)-2-Pyrrolidone-5-carboxylicacid  95%

  • 4042-36-8

  • 422614-10G

  • 779.22CNY

  • Detail

4042-36-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-oxo-D-proline

1.2 Other means of identification

Product number -
Other names (R)-5-Oxopyrrolidine-2-carboxylic Acid

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:4042-36-8 SDS

4042-36-8Synthetic route

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate; platinum In water for 4h; Ambient temperature;95%
tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate
307304-62-7

tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With water In 1,4-dioxane for 12h; Hydrolysis; cyclization; Heating;45%
D-Glutamic acid
6893-26-1

D-Glutamic acid

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With water for 63h; Heating;
In water for 72h; Heating;
With D-glutamate cyclase from mouse In methanol at 37℃; for 1h; pH=8; Kinetics; Enzymatic reaction;
With sodium hydroxide In ethanol; water at 20℃; for 48h;
With DL-dithiothreitol; D-glutamate cyclase; manganese(ll) chloride In aq. buffer at 37℃; for 1h; pH=8; Kinetics; Enzymatic reaction;
L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
In water at 140℃; Rate constant; pH 8.0;
dextrorotatory pyroglutamamide

dextrorotatory pyroglutamamide

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With barium dihydroxide; water
inactive form

inactive form

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With Quinine
ethyl (R)-2-pyrrolidone-5-carboxylate
68766-96-1

ethyl (R)-2-pyrrolidone-5-carboxylate

A

ethanol
64-17-5

ethanol

B

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics;
methyl (2R)-pyroglutamate
64700-65-8

methyl (2R)-pyroglutamate

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / NaBH4 / ethanol / 2 h / Ambient temperature
2: 95 percent / NaHCO3, O2 / Pt / H2O / 4 h / Ambient temperature
View Scheme
Pyroglutamic acid
149-87-1

Pyroglutamic acid

A

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

B

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With Ν,Ν-dimethyldehydroabietylamine In chloroform-d1 at 27℃; Resolution of racemate;
ethanol
64-17-5

ethanol

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

ethyl (R)-2-pyrrolidone-5-carboxylate
68766-96-1

ethyl (R)-2-pyrrolidone-5-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 20℃;100%
With thionyl chloride at 80℃; for 1.5h;94%
sulfuric acid Reflux;
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

tert-butyl (R)-5-oxopyrrolidine-2-carboxylate
205524-46-5

tert-butyl (R)-5-oxopyrrolidine-2-carboxylate

Conditions
ConditionsYield
With perchloric acid In water100%
With perchloric acid In water at 20℃; for 24h; Inert atmosphere;100%
(R)-4-(3,5-dimethylisoxazol-4-yl)-N1-(1-(methylsulfonyl)pyrrolidin-3-yl)benzene-1,2-diamine

(R)-4-(3,5-dimethylisoxazol-4-yl)-N1-(1-(methylsulfonyl)pyrrolidin-3-yl)benzene-1,2-diamine

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R)-N-(5-(3,5-dimethylisoxazol-4-yl)-2-(((R)-1-(methylsulfonyl)pyrrolidin-3-yl)amino)phenyl)-5-oxopyrrolidine-2-carboxamide

(R)-N-(5-(3,5-dimethylisoxazol-4-yl)-2-(((R)-1-(methylsulfonyl)pyrrolidin-3-yl)amino)phenyl)-5-oxopyrrolidine-2-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h;100%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate
128899-31-0

<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
Stage #1: D-pyrrolidone-5-carboxylic acid With thionyl chloride In methanol at 20℃; for 4h;
Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 15h;
Stage #3: p-toluenesulfonyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 16h;
100%
methanol
67-56-1

methanol

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

methyl (2R)-pyroglutamate
64700-65-8

methyl (2R)-pyroglutamate

Conditions
ConditionsYield
With thionyl chloride for 12h;98%
With thionyl chloride 1.) 0 deg C, 30 min, 2.) room temp., 3 h;95%
With sulfuric acid at 20℃; for 24h;95%
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester
113994-41-5

2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

amlodipine (R)-(+)-pyroglutamate

amlodipine (R)-(+)-pyroglutamate

Conditions
ConditionsYield
95.1%
1-(2-tert-butylphenyl)piperazine dihydrochloride

1-(2-tert-butylphenyl)piperazine dihydrochloride

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(5R)-5-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}pyrrolidin-2-one
1252657-17-2

(5R)-5-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}pyrrolidin-2-one

Conditions
ConditionsYield
Stage #1: 1-(2-tert-butylphenyl)piperazine dihydrochloride; D-pyrrolidone-5-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile at 20℃; for 16h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
94%
C12H11Cl2N3O

C12H11Cl2N3O

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R,E)-N-(4-(6,7-dichloro-4-oxoquinazolin-3(4H)-yl)but-2-en-1-yl)-5-oxopyrrolidine-2-carboxamide

(R,E)-N-(4-(6,7-dichloro-4-oxoquinazolin-3(4H)-yl)but-2-en-1-yl)-5-oxopyrrolidine-2-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 2h;90%
(S)-benzyl 2-amino-3-(4-methoxyphenyl)propanoate
55456-41-2

(S)-benzyl 2-amino-3-(4-methoxyphenyl)propanoate

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(S)-benzyl 3-(4-methoxyphenyl)-2-((R)-5-oxopyrrolidine-2-carboxamido)propanoate

(S)-benzyl 3-(4-methoxyphenyl)-2-((R)-5-oxopyrrolidine-2-carboxamido)propanoate

Conditions
ConditionsYield
Stage #1: (S)-benzyl 2-amino-3-(4-methoxyphenyl)propanoate With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: D-pyrrolidone-5-carboxylic acid With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;
89%
C27H37N3O5

C27H37N3O5

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

C27H34N4O5

C27H34N4O5

Conditions
ConditionsYield
Stage #1: C27H37N3O5 With trifluoroacetic acid In dichloromethane at 0 - 20℃;
Stage #2: D-pyrrolidone-5-carboxylic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
89%
tert-butyl (3R)-3-amino-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

tert-butyl (3R)-3-amino-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

tert-butyl (3R)-3-amino-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (2R)-5-oxopyrrolidine-2-carboxylate

tert-butyl (3R)-3-amino-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (2R)-5-oxopyrrolidine-2-carboxylate

Conditions
ConditionsYield
In ethanol at 63℃;89%
In ethanol at 63℃; Inert atmosphere;89%
In ethanol at 63℃;89%
In ethanol at 65℃;19.2 g
silver(l) oxide
20667-12-3

silver(l) oxide

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

[Ag2(R-pyrrld)(S-pyrrld)]

[Ag2(R-pyrrld)(S-pyrrld)]

Conditions
ConditionsYield
In water to suspn. of Ag2O in water was added soln. of ligand in water, stirred for 2 h; filtered off, acetone vapor was diffused, collected, washed with Et2O, dried in vacuo; elem. anal.;86.2%
C16H21F3N2O2S*C2HF3O2

C16H21F3N2O2S*C2HF3O2

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

thioacetic acid S-[(S)-6-[((R)-5-oxo-pyrrolidine-2-carbonyl)-amino]-6-(3-trifluoromethyl-phenylcarbamoyl)-hexyl] ester
1428535-89-0

thioacetic acid S-[(S)-6-[((R)-5-oxo-pyrrolidine-2-carbonyl)-amino]-6-(3-trifluoromethyl-phenylcarbamoyl)-hexyl] ester

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;84%
2-{(5-methoxy-1H-indole-3yl)-methylene}-N-pentylhydrazine carboxidamide

2-{(5-methoxy-1H-indole-3yl)-methylene}-N-pentylhydrazine carboxidamide

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(x)C5H7NO3*C16H23N5O

(x)C5H7NO3*C16H23N5O

Conditions
ConditionsYield
In methanol at 20℃; for 1h;84%
C16H24N2O2S*C2HF3O2

C16H24N2O2S*C2HF3O2

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

thioacetic acid S-{(S)-6-[((R)-5-oxo-pyrrolidine-2-carbonyl)-amino]-6-m-tolylcarbamoyl-hexyl} ester
1428535-79-8

thioacetic acid S-{(S)-6-[((R)-5-oxo-pyrrolidine-2-carbonyl)-amino]-6-m-tolylcarbamoyl-hexyl} ester

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;80%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;
para-difluorobenzene
540-36-3

para-difluorobenzene

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

C10H9F2NO

C10H9F2NO

Conditions
ConditionsYield
With methanesulfonic acid; phosphorus pentoxide; Eaton’s reagent at 50 - 65℃; for 27h; Temperature; Inert atmosphere;78%
D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

methyl (2R)-pyroglutamate
64700-65-8

methyl (2R)-pyroglutamate

Conditions
ConditionsYield
With thionyl chloride In methanol at 20℃; Inert atmosphere;75%
allyl alcohol
107-18-6

allyl alcohol

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

allyl (R)-5-oxopyrrolidine-2-carboxylate

allyl (R)-5-oxopyrrolidine-2-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 23℃; for 3h; Inert atmosphere;71%
D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(-)-8-(4-phenylphenyl)menthol
322640-14-2

(-)-8-(4-phenylphenyl)menthol

(1R,2S,5R)-2-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)-5-methylcyclohexyl (R)-5-oxopyrrolidine-2-carboxylate

(1R,2S,5R)-2-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)-5-methylcyclohexyl (R)-5-oxopyrrolidine-2-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 23℃; for 24.5h; Inert atmosphere;69%
(1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-10-ol

(1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-10-ol

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R)-5-((1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-10-hydroxy-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-carbonyl) pyrrolidin-2-one

(R)-5-((1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-10-hydroxy-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphtho[1,2-e]indol-3-carbonyl) pyrrolidin-2-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 14h;58%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(S)-3-hydroxypiperidine D-pyroglutamate

(S)-3-hydroxypiperidine D-pyroglutamate

Conditions
ConditionsYield
In ethanol for 1.5h; Time; Reflux; Large scale;55%
benzylamine
100-46-9

benzylamine

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R)-5-oxopyrrolidine-2-carboxylic acid benzylamide
178327-71-4

(R)-5-oxopyrrolidine-2-carboxylic acid benzylamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 0 - 20℃; for 3h;48%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 3h; Cooling with ice;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 3h; Cooling with ice;
(S)-3-aminomethyl-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-5-fluoro-N2-[1-(4-fluorophenyl)ethyl]pyridine-2,6-diamine
905585-65-1

(S)-3-aminomethyl-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-5-fluoro-N2-[1-(4-fluorophenyl)ethyl]pyridine-2,6-diamine

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R)-N-((6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-((S)-1-(4-fluorophenyl)ethylamino)pyridin-3-yl)methyl)-5-oxo-pyrrolidine-2-carboxamide
905586-73-4

(R)-N-((6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-2-((S)-1-(4-fluorophenyl)ethylamino)pyridin-3-yl)methyl)-5-oxo-pyrrolidine-2-carboxamide

Conditions
ConditionsYield
Stage #1: (S)-3-aminomethyl-N6-(5-cyclopropyl-1H-pyrazol-3-yl)-5-fluoro-N2-[1-(4-fluorophenyl)ethyl]pyridine-2,6-diamine; D-pyrrolidone-5-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 1h;
Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; dichloromethane
43%
(S)-N-cinnamoylserinecyclohexylamide

(S)-N-cinnamoylserinecyclohexylamide

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(S)-N-cinnamoylserine{3-(R)-pyroglutamoyl}cyclohexylamide

(S)-N-cinnamoylserine{3-(R)-pyroglutamoyl}cyclohexylamide

Conditions
ConditionsYield
With oxalyl dichloride; triethylamine In N,N-dimethyl-formamide25%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one
128899-30-9, 100548-49-0, 106191-02-0

(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

Conditions
ConditionsYield
Stage #1: D-pyrrolidone-5-carboxylic acid With thionyl chloride In methanol at 0 - 20℃; for 1h;
Stage #2: With sodium tetrahydroborate In ethanol at 0 - 20℃; for 16h;
Stage #3: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;
24%
[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine hydrochloride

[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine hydrochloride

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-5-oxo-D-prolineamide

N-[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-5-oxo-D-prolineamide

Conditions
ConditionsYield
Stage #1: D-pyrrolidone-5-carboxylic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In tetrahydrofuran at 0℃; for 2h;
Stage #2: [3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amine hydrochloride With 4-methyl-morpholine In tetrahydrofuran; DMF (N,N-dimethyl-formamide) at 20℃; for 15h;
Stage #3: With sodium methylate In methanol at 20℃; for 1h;
8%
7-fluoronaphtho[2,1-d]thiazol-2-amine

7-fluoronaphtho[2,1-d]thiazol-2-amine

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R)-N-(7-fluoronaphtho[2,1-d]thiazol-2-yl)-5-oxopyrrolidine-2-carboxamide

(R)-N-(7-fluoronaphtho[2,1-d]thiazol-2-yl)-5-oxopyrrolidine-2-carboxamide

Conditions
ConditionsYield
Stage #1: D-pyrrolidone-5-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: 7-fluoronaphtho[2,1-d]thiazol-2-amine In N,N-dimethyl-formamide at 60℃; for 16h;
5%

4042-36-8Relevant articles and documents

A colorimetric assay method for measuring D-glutamate cyclase activity

Ariyoshi, Makoto,Hamase, Kenji,Homma, Hiroshi,Katane, Masumi,Matoba, Satoaki,Mita, Masashi,Miyamoto, Tetsuya,Motoda, Risa,Nakayama, Kazuki,Saitoh, Yasuaki,Sakai-Kato, Kumiko,Sekine, Masae,Tateishi, Shuhei

, (2020)

In mammals, metabolism of free D-glutamate is regulated by D-glutamate cyclase (DGLUCY), which reversibly converts D-glutamate to 5-oxo-D-proline and H2O. Metabolism of these D-amino acids by DGLUCY is thought to regulate cardiac function. In this study, we established a simple, accurate, and sensitive colorimetric assay method for measuring DGLUCY activity. To this end, we optimized experimental procedures for derivatizing 5-oxo-D-proline with 2-nitrophenylhydrazine hydrochloride. 5-Oxo-D-proline was derivatized with 2-nitrophenylhydrazine hydrochloride in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide as a catalyst to generate the acid hydrazides, whose levels were then determined using a colorimetric method. Under optimized conditions, we examined the sensitivity and accuracy of the colorimetric method and compared our technique with other methods by high-performance liquid chromatography with ultraviolet–visible or fluorescence detection. Moreover, we assessed the suitability of this colorimetric method for measuring DGLUCY activity in biological samples. Our colorimetric method could determine DGLUCY activity with adequate validity and reliability. This method will help to elucidate the relationship among DGLUCY activity, the physiological and pathological roles of D-glutamate and 5-oxo-D-proline, and cardiac function.

Structural and enzymatic properties of mammalian D-glutamate cyclase

Katane, Masumi,Ariyoshi, Makoto,Tateishi, Shuhei,Koiwai, Sachi,Takaku, Kaoruko,Nagai, Kenichiro,Nakayama, Kazuki,Saitoh, Yasuaki,Miyamoto, Tetsuya,Sekine, Masae,Mita, Masashi,Hamase, Kenji,Matoba, Satoaki,Homma, Hiroshi

, p. 10 - 18 (2018/07/25)

D-Glutamate cyclase (DGLUCY) is a unique enzyme that reversibly converts free D-glutamate to 5-oxo-D-proline and H2O. Mammalian DGLUCY is highly expressed in the mitochondrial matrix in the heart, and its downregulation disrupts D-glutamate and/or 5-oxo-D-proline levels, contributing to the onset and/or exacerbation of heart failure. However, detailed characterisation of DGLUCY has not yet been performed. Herein, the structural and enzymatic properties of purified recombinant mouse DGLUCY were examined. The results revealed a dimeric oligomerisation state, and both D-glutamate-to-5-oxo-D-proline and 5-oxo-D-proline-to-D-glutamate reactions were catalysed in a stereospecific manner. Catalytic activity is modulated by divalent cations and nucleotides including ATP and ADP. Interestingly, the presence of Mn2+ completely abolished the 5-oxo-D-proline-to-D-glutamate reaction but stimulated the D-glutamate-to-5-oxo-D-proline reaction. The optimum pH is ~8.0, similar to that in the mitochondrial matrix, and the catalytic efficiency for D-glutamate is markedly higher than that for 5-oxo-D-proline. These findings suggest that DGLUCY functions as a metalloenzyme that degrades D-glutamate in the mitochondrial matrix in mammalian cells. The results also provide insight into the correlation between DGLUCY enzyme activity and the physiological and pathological roles of D-glutamate and 5-oxo-D-proline in cardiac function, which is of relevance to the risk of onset of heart failure.

Mapping the substrate selectivity of new hydrolases using colorimetric screening: Lipases from Bacillus thermocatenulatus and Ophiostoma piliferum, esterases from Pseudomonas fluorescens and Streptomyces diastatochromogenes

Liu, Andrew Man Fai,Somers, Neil A.,Kazlauskas, Romas J.,Brush, Terry S.,Zocher, Frank,Enzelberger, Markus M.,Bornscheuer, Uwe T.,Horsman, Geoff P.,Mezzetti, Alessandra,Schmidt-Dannert, Claudia,Schmid, Rolf D.

, p. 545 - 556 (2007/10/03)

Recent advances in biochemistry and molecular biology have simplified the discovery and preparation of new hydrolases. Although these hydrolases might solve problems in organic synthesis, measuring their selectivity, especially enantioselectivity, remains tedious and time consuming. Recently, we developed a colorimetric screening method to measure the enantioselectivity of hydrolases. Here we apply this rapid screening method to map the substrate selectivity of four new hydrolases: lipases from the thermophilic Bacillus thermocatenulatus (DSM 730, BTL2) and a filamentous fungus Ophiostoma piliferum (NRRL 18917, OPL) and esterases from two bacteria, Pseudomonas fluorescens (SIK-W1, esterase I, PFE) and Streptomyces diastatochromogenes (Tue 20, SDE). We screened a general library of 29 substrates and a chiral library of 23 pairs of enantiomers. All four hydrolases catalysed the hydrolysis of unnatural substrates, but the two lipases accepted a broader range of substrates than the two esterases. As expected, the two lipases favoured more hydrophobic substrates, while the two esterases showed a preference for smaller substrates. Several moderately enantioselective reactions were identified for the solketal esters: BTL2, butyrate, E = 7.9 (R); octanoate, E = 4.9 (R) and 3-bromo-2-methyl propionate methyl esters, PFE, E = 12 (S); SDE, E = 5.6 (S). OPL showed low enantioselectivity toward all substrates tested. The current colorimetric screen could not measure the selectivity for several slow-reacting substrates. Traditional screening identified high enantioselectivity of BTL2 and PFE toward one of these slow substrates, 1-phenylethyl acetate (E>50).

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 4042-36-8