Conditions | Yield |
---|---|
durch Einw. von gaerender Hefe; | |
durch Einw. von Penicillium purpurogenum; | |
Einw. von Penicillium glaucum; |
Conditions | Yield |
---|---|
Enzymatische Herstellung; |
N-benzoylglutamic acid
D-Glutamic acid
Conditions | Yield |
---|---|
Enzymatische Herstellung; |
N-benzyloxycarbonyl-DL-glutamic acid
D-Glutamic acid
Conditions | Yield |
---|---|
With sodium hydroxide; aniline; papain Hydrogenolyse der dabei unveraendert zurueckbleibenden N-Carbobenzoxy-D-glutaminsaeure an Palladium in Methanol; | |
Enzymatische Herstellung; |
5-oxo-1-(toluene-4-sulfonyl)-D-proline
D-Glutamic acid
Conditions | Yield |
---|---|
With sodium hydroxide anschliessend mit Natrium und NH3; | |
With hydrogen bromide anschliessend mit Natrium und NH3; |
Conditions | Yield |
---|---|
In water at 140℃; Rate constant; pH 8.0; | |
With L-amino acid deaminase from Proteus mirabilis; Burkholderia stabilis formate dehydrogenase; meso-diaminopimelate dehydrogenase from Symbiobacterium thermophilum mutant H227V; sodium formate; ammonium chloride; NADPH In aq. phosphate buffer at 45℃; pH=9; Enzymatic reaction; |
Conditions | Yield |
---|---|
With methyloxirane In ethanol for 0.5h; Heating; Yield given; |
(R)-2-amino-4-cyanobutanoic acid
D-Glutamic acid
Conditions | Yield |
---|---|
With hydrogenchloride at 95℃; |
N-[(1,1-dimethylethoxy)carbonyl]-D-glutamic acid
A
D-Glutamic acid
B
L-glutamic acid
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 1h; Ambient temperature; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
Yield given. Yields of byproduct given; |
D-Glutamic acid
Conditions | Yield |
---|---|
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; | |
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 7.5; enzymatic reaction; |
Conditions | Yield |
---|---|
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 8.0; enzymatic reaction; | |
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; |
Conditions | Yield |
---|---|
With HEPES buffer; IFAB-PX60 conjugate at 37℃; for 24h; Product distribution; enantioselectivity and substrate specificity, various IFAB-PX conjugates and keto acids; | |
With enzym based on a mutant form of intestinal fatty acid binding protein; rac-Ala-OH at 37℃; for 24h; Product distribution; Rate constant; var. amino acids; | |
With sodium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid In water at 37℃; adipocyte lipid binding protein containing 5-(2-pyridylthio)pyridoxamine cofactor; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With IFABP - methylpyridoxamine conjugate; ›Tyr In various solvent(s) at 37℃; for 120h; pH=7.71; Enzyme kinetics; Product distribution; Further Variations:; Reagents; transamination; | |
With C12H18N4O2*ClH; 2,2-diphenylglycine In methanol; water at 20℃; for 6h; enantioselective reaction; | A n/a B n/a |
(R)-4-Amino-5-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-oxo-pentanoic acid ethyl ester
D-Glutamic acid
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 0℃; for 1h; |
hydrogenchloride
5-oxo-pyrrolidine-2-carboxylic acid amide
D-Glutamic acid
Conditions | Yield |
---|---|
levorotatory pyroglutamamide; |
Conditions | Yield |
---|---|
levorotatory pyroglutamamide; |
D-Glutamic acid
Conditions | Yield |
---|---|
With hydrogenchloride Hydrolysis; |
Conditions | Yield |
---|---|
at 100℃; |
D-Glutamic acid
Conditions | Yield |
---|---|
With water; strychnidin-10-one Spaltung ueber mehrere Stufen; |
D-Glutamic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
D-Glutamic acid
Conditions | Yield |
---|---|
Hydrolysis.durch selektive Hydrolyse mit Hilfe eines Enzym-Praeparats aus Nieren und Kochen der unveraendert zurueckbleibenden N-Chloracetyl-D-glutaminsaeure mit 2n-HCl; |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium carbonate 1.) MeCN, 50-55 deg C; Multistep reaction. Yields of byproduct given; | |
With hydrogenchloride; potassium carbonate 1.) MeCN, 50-55 deg C; Yield given. Multistep reaction; |
sulfuric acid
α-N-phenylacetyl-L-glutamine
A
phenylacetic acid
B
D-Glutamic acid
Conditions | Yield |
---|---|
Stage #1: L-glutamic acid With mercaptoethyl alcohol; Tris-HCl buffer; Chitopearl immobilized glutamate racemase In water at 40℃; pH=8; Racemization; Stage #2: With mercaptoethyl alcohol; Tris-HCl buffer; Chitopearl immobilized L-glutamate oxidase In water at 40℃; pH=8; Oxidation; | A n/a B 0.0045 mmol |
α-ketoglutaric acid
Phenylalanine
A
D-Glutamic acid
B
L-glutamic acid
C
2-oxo-3-(phenyl)propionic acid
Conditions | Yield |
---|---|
With IFABP-V60C; R126M-S-pyridoxamine In water at 37℃; pH=7.5; Kinetics; Enzyme kinetics; Further Variations:; Reagents; Enzymatic reaction; |
methanol
D-Glutamic acid
D-glutamic acid dimethyl ester hydrochloride
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 20℃; for 16h; | 100% |
With tertiary butyl chloride at 20℃; for 16h; | 100% |
With hydrogenchloride | 96.3% |
D-Glutamic acid
di-tert-butyl dicarbonate
N-[(1,1-dimethylethoxy)carbonyl]-D-glutamic acid
Conditions | Yield |
---|---|
With triethylamine In water; N,N-dimethyl-formamide for 1h; | 100% |
In water; N,N-dimethyl-formamide at 20 - 30℃; for 1h; | 90% |
Conditions | Yield |
---|---|
Stage #1: methanol; D-Glutamic acid With thionyl chloride at 30℃; for 6h; Stage #2: di-tert-butyl dicarbonate With triethylamine In 1,4-dioxane; water | 99% |
Conditions | Yield |
---|---|
Stage #1: methanol; D-Glutamic acid With thionyl chloride at 20℃; for 20h; Stage #2: In toluene for 2h; Reflux; | 98% |
D-Glutamic acid
benzyl chloroformate
N-benzyloxycarbonyl-D-glutamic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 60℃; for 0.25h; | 96% |
With sodium hydrogencarbonate | 94% |
With sodium hydrogencarbonate; sodium carbonate In water; acetone at 0 - 20℃; for 36h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With sodium carbonate In ethanol boiling; | 95% |
chloro-trimethyl-silane
D-Glutamic acid
di-tert-butyl dicarbonate
α-Methyl (2R)-N-(tert-butoxycarbonyl)glutamate ester
Conditions | Yield |
---|---|
Stage #1: chloro-trimethyl-silane; D-Glutamic acid In methanol at 20℃; Cooling with ice; Stage #2: di-tert-butyl dicarbonate With triethylamine at 20℃; for 3h; | 95% |
D-Glutamic acid
benzyl alcohol
D-glutamic acid-5-benzyl ester
Conditions | Yield |
---|---|
With boron trifluoride; sodium sulfate In diethyl ether at 20℃; for 15h; | 94% |
With boron trifluoride; sodium sulfate In diethyl ether at 20℃; for 15h; | 94% |
With boron trifluoride diethyl etherate at 20℃; for 15h; | 78% |
D-Glutamic acid
(R)-tetrahydro-5-oxo-2-furancarboxylic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at -5 - 20℃; | 93% |
With hydrogenchloride; sodium nitrite Ambient temperature; | 89.9% |
With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 12h; | 78% |
Conditions | Yield |
---|---|
at 70℃; | 91.7% |
formaldehyd
D-Glutamic acid
benzyl chloroformate
(4R)-4-(2-Carboxyethyl)-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one
Conditions | Yield |
---|---|
Stage #1: D-Glutamic acid; benzyl chloroformate With sodium hydrogencarbonate In water at 20℃; for 16h; Stage #2: formaldehyd With toluene-4-sulfonic acid In toluene for 0.333333h; Heating; Further stages.; | 91% |
Conditions | Yield |
---|---|
Stage #1: D-Glutamic acid With pyridine; chloro-trimethyl-silane In dichloromethane for 1h; Stage #2: n-hexadecanoyl chloride In dichloromethane for 1.83333h; | 90% |
D-Glutamic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrate In water at -5 - 25℃; for 0.111167h; | 89.6% |
1-Heptadecanol
D-Glutamic acid
(R)-2-Amino-pentanedioic acid diheptadecyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene Heating; | 89% |
Conditions | Yield |
---|---|
With potassium hydroxide; thionyl chloride at 150℃; | 88% |
Stage #1: ethanol; D-Glutamic acid With thionyl chloride Stage #2: Stage #3: In toluene Reflux; |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; for 16h; | 88% |
With thionyl chloride at 0 - 20℃; for 10h; | 88% |
With thionyl chloride at 0 - 20℃; |
D-Glutamic acid
sodium methylate
1,5-dimethyl (2R)-2-aminopentanedioate
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; for 12.5h; | 87% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene Heating; | 86% |
Conditions | Yield |
---|---|
Stage #1: D-Glutamic acid With pyridine; chloro-trimethyl-silane In dichloromethane for 1.16667h; Stage #2: tetradecanoyl chloride In dichloromethane for 1.83333h; | 86% |
Conditions | Yield |
---|---|
Stage #1: methanol; D-Glutamic acid With chloro-trimethyl-silane at 0 - 23℃; for 17.0833h; Stage #2: With copper(ll) sulfate pentahydrate; triflic azide; sodium hydrogencarbonate In methanol; water; toluene at 0 - 23℃; for 2.66667h; | 86% |
Conditions | Yield |
---|---|
In water ligand was added to aq. soln. of Er(ClO4)3, stirred at 80°C, aq. soln. of NaOH was added pH 2; filtered, allowed to stand at room temp. for 1 wk, filtered, washed withTHF/ether, dried; elem. anal.; | 85% |
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 15 - 20℃; for 2h; | 85% |
D-Glutamic acid
carbonic acid 2,5-dioxopyrrolidin-1-yl ester 4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)benzyl ester
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; water at 25℃; | 83% |
D-Glutamic acid
toluene-4-sulfonic acid
benzyl alcohol
D-glutamic acid dibenzyl ester p-toluenesufonate salt
Conditions | Yield |
---|---|
In benzene for 7h; Reflux; | 83% |
In benzene for 26h; Reflux; | 77% |
In toluene at 20℃; Inert atmosphere; |
D-Glutamic acid
1-dodecyl alcohol
(R)-2-Amino-pentanedioic acid didodecyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene Heating; | 82% |
D-Glutamic acid
N-Fmoc-D-glutamic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In [(2)H6]acetone; water | 81% |
With sodium hydrogencarbonate In [(2)H6]acetone; water | 81% |
D-Glutamic acid
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
N-Fmoc-D-glutamic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 20℃; for 72h; Cooling with ice; | 81% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 2018℃; Inert atmosphere; regioselective reaction; | 80% |
With chloro-trimethyl-silane | 75% |
With chloro-trimethyl-silane at 20℃; for 18h; | 65% |
D-Glutamic acid
[NiCl2(N,N-bis(dicyclohexylphosphinomethyl)methylamine)]
Conditions | Yield |
---|---|
With silver(l) oxide In dichloromethane (N2); Schlenk technique; Ag2O added to stirred sol. of Ni-complex, glutamic acid added, mixt. refluxed for 8 h; mixt. filtered (Celite), evapd., product precipitated with diethyl ether, filtered, dried; elem. anal.; | 80% |
Conditions | Yield |
---|---|
Stage #1: D-Glutamic acid With hydrogenchloride; water; sodium nitrite at -5℃; for 16h; Stage #2: methanol In water for 12h; Reflux; | 80% |
Stage #1: D-Glutamic acid With hydrogenchloride; sodium nitrite In water at -10 - 20℃; for 18h; Stage #2: methanol With hydrogenchloride; water for 12h; Reflux; | 60% |
Stage #1: D-Glutamic acid With hydrogenchloride; sodium nitrite In water at -10 - 20℃; for 18h; Stage #2: methanol With hydrogenchloride In water for 12h; Reflux; | 60% |
The IUPAC name of D-Glutamic acid is (2R)-2-aminopentanedioic acid. With the CAS registry number 6893-26-1, it is also named as D-2-Aminopentanedioic acid. The product's categories are Amino Acids Series; Glutamic Acid [Glu, E]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids; Biochemistry; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Nutritional Supplements; Amino Acids; Glutamate Receptor. Besides, it is white crystalline powder, which should be stored at room temperature. In addition, its molecular formula is C5H9NO4 and molecular weight is 147.13.
The other characteristics of this product can be summarized as: (1)EINECS: 230-000-8; (2)ACD/LogP: -1.44; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): -4.7; (5)ACD/LogD (pH 7.4): -4.93; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 5; (11)#H bond donors: 4; (12)#Freely Rotating Bonds: 5; (13)Index of Refraction: 1.522; (14)Molar Refractivity: 31.83 cm3; (15)Molar Volume: 104.3 cm3; (16)Density: 1.409 g/cm3; (17)Flash Point: 155.7 °C; (18)Melting point: 200-202 °C; (19)alpha: -31.3 °(c=10, 2 N HCl); (20)Water solubility: 7 g/L (20 °C); (21)Enthalpy of Vaporization: 63.39 kJ/mol; (22)Boiling Point: 333.8 °C at 760 mmHg; (23)Vapour Pressure: 2.55E-05 mmHg at 25 °C.
Preparation of D-Glutamic acid: frist of all, please use acylase to treat Acetyl-DL-glutamic acid. And then you would obtain this chemical after refining and drying.
Uses of D-Glutamic acid: this chemical is used as amino acids medicine. It can also used for biochemical studies. Additionally, it can react with phenylmethanol to get D-glutamic acid-5-benzyl ester.
This reaction needs H2SO4. The yield is 58.9 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing to avoid contact with skin and eyes.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(O)CC[C@@H](N)C(=O)O
(2)InChI: InChI=1/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1
(3)InChIKey: WHUUTDBJXJRKMK-GSVOUGTGBI
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