Conditions | Yield |
---|---|
With CC10H14NOSCH2CH2CH3N(CH3)2 (5); zinc diacetate In methanol at 30℃; Product distribution; pH 4.00; other reagent; | A 95% B 5% |
With 5-((3-(dimethylamino)propyl)thio)-4-(aminomethyl)-3-hydroxyl-5,6,7,8-tetraquinoline In methanol at 30℃; Product distribution; stereoselective transaminations at pH=4.00, various reagents; | A 96 % Chromat. B 4 % Chromat. |
With C12H18N4O2*ClH; 2,2-diphenylglycine In methanol; water at 20℃; for 6h; enantioselective reaction; | A n/a B n/a |
With isopropylamine In aq. buffer for 48h; pH=7.0; Time; Enzymatic reaction; Overall yield = 90 %; | A n/a B n/a |
(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
L-Norvaline
Conditions | Yield |
---|---|
With hydrogen; palladium dichloride In tetrahydrofuran; ethanol under 2068.6 Torr; for 21h; | 93% |
With hydrogen; palladium dichloride In ethanol at 25℃; under 1034.3 Torr; Yield given; |
(1S,2S,5S,9S)-2,10,10-Trimethyl-5-propyl-3-oxa-6-aza-tricyclo[7.1.1.02,7]undec-6-en-4-one
L-Norvaline
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at 70℃; for 3h; | 92% |
Conditions | Yield |
---|---|
With sodium formate; ammonium chloride; NADH In aq. phosphate buffer at 25℃; for 6h; pH=8.0; Kinetics; Reagent/catalyst; Green chemistry; Enzymatic reaction; | 84.1% |
With glutamate dehydrogenase; L-glutamic acid; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; branched-chain amino acid aminotransferase; NADH In isopropyl alcohol at 35℃; for 5h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 59.1% |
With L-2-aminobutyric acid; branched-chain transaminase from Escherichiacoli; S-selective ω-transaminase from Ochrobactrum anthropi; (3-hydroxy-5-hydroxymethyl)-2-methylisonicotinic acid 5-phosphate; isopropylamine In aq. phosphate buffer for 9h; pH=7; | n/a |
DL-α-alanyl-DL-norvaline
A
L-alanin
B
D-Alanine
C
D-norvaline
D
L-Norvaline
Conditions | Yield |
---|---|
With (S)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 1h; Ambient temperature; | A 78.31% B 21.69% C 60.57% D 39.43% |
With (S)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 3h; Ambient temperature; | A 76.83% B 23.15% C 73.8% D 26.2% |
With (R)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 1h; Ambient temperature; | A 26.8% B 73.2% C 42.16% D 57.84% |
With (R)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate for 1h; Ambient temperature; | A 26.8% B 73.2% C 42.16% D 57.84% |
tert-butyl-(2S,3S)-1,2-dihydroxyhexan-3-ylcarbamate
L-Norvaline
Conditions | Yield |
---|---|
Stage #1: tert-butyl-(2S,3S)-1,2-dihydroxyhexan-3-ylcarbamate With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran for 12h; Heating; | 65% |
(2S)-(N-para-toluenesulphonylamino)pentanoic acid tert-butyl ester
L-Norvaline
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid; phenol for 24h; Ambient temperature; | 62% |
With hydrogen bromide; acetic acid 1.) phenol, 25 deg C, 24 h; |
((S)-1-Cyano-butyl)-carbamic acid methyl ester
L-Norvaline
Conditions | Yield |
---|---|
With hydrogenchloride In water for 7h; Heating; | 60% |
L-Norvaline
Conditions | Yield |
---|---|
With hydrogen; palladium on carbon In water at 50℃; under 16501.7 Torr; for 47h; | 41.5% |
N-acetylnorvaline
A
L-Norvaline
B
N-acetyl-D-norvaline
Conditions | Yield |
---|---|
With potassium hydroxide; Aspergillus acylase I pH 7.5-8.0; Yields of byproduct given; | A 33% B n/a |
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2; | |
With lipase AS 'Amano' at 35℃; for 24h; pH=6.5; Enzymatic reaction; enantioselective reaction; | A n/a B n/a |
α-ketovalerate
L-Norvaline
Conditions | Yield |
---|---|
With L-glutamic acid; pyridoxal 5'-phosphate In water at 40℃; for 18h; E.coli Aspartate transaminase, pH 8; | 32% |
With pyridoxal 5'-phosphate; Paracoccus denitrificans ω-transaminase; isopropylamine In aq. phosphate buffer for 1.66667h; pH=7; Enzymatic reaction; |
N-formyl-D,L-norvaline
L-Norvaline
Conditions | Yield |
---|---|
beim Verseifen; | |
Multi-step reaction with 2 steps 2: Hydrolysis View Scheme | |
With water; cobalt(II) chloride for 0.8h; pH=8; Enzymatic reaction; |
N-formyl-L-norvaline
L-Norvaline
Conditions | Yield |
---|---|
Hydrolysis; |
N-acetylnorvaline
L-Norvaline
Conditions | Yield |
---|---|
With (R)-1-phenyl-ethyl-amine | |
With acylase from Aspergillus oryzae; water at 20 - 37℃; |
Conditions | Yield |
---|---|
mit Hilfe eines Enzym-Praeparats aus Schweine-Nieren; |
N,N-dibenzyl-L-norvaline
L-Norvaline
Conditions | Yield |
---|---|
With hydrogenchloride; palladium Hydrogenation; |
N-Acetyl-L-2-aminopentanoic acid
L-Norvaline
Conditions | Yield |
---|---|
With Aspergillus oryzae acylase relative rates; | |
With pig kidney acylase I In phosphate buffer at 37℃; for 0.166667h; pH=7.4; Enzyme kinetics; Deacetylation; |
Conditions | Yield |
---|---|
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2; |
(R)-2-Azido-pentanoic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
A
D-norvaline
B
L-Norvaline
Conditions | Yield |
---|---|
With titanium tetrakis(benzyl alkoxide); hydrogen; Pd-BaSO4 1.) benzyl alcohol, 130 gradC 2.) EtOH, 1 atm, r.t.; Yield given. Multistep reaction. Yields of byproduct given; |
N-Methoxyacetyl norvaline
A
L-Norvaline
B
N-Methoxyacetyl D-norvaline
Conditions | Yield |
---|---|
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2; |
L-Norvaline
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In ethanol for 1h; |
diethylaluminium cyanide
(S)-N-(butylidene)-4-methylbenzenesulfinamide
L-Norvaline
Conditions | Yield |
---|---|
With hydrogenchloride 1.) Et2O, from -78 to -15 degC; 2.) reflux; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride 1.) THF, from -78 to -40 degC; 2.) reflux; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate In water; tert-butyl alcohol at 40℃; for 4h; alcalase, pH=8.5; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With Alcalase; pyridoxal 5'-phosphate; water In tert-butyl alcohol at 40℃; for 4h; pH=8.5; racemization of D-enantiomer; kinetic res.; Title compound not separated from byproducts; |
(R)-2-((4S,5R)-2-Oxo-4,5-diphenyl-oxazolidin-3-yl)-pent-4-enoic acid benzyl ester
A
D-norvaline
B
L-Norvaline
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In tetrahydrofuran; methanol under 3102.9 Torr; for 10.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With phosphate buffer; Humicola amino esterase Ambient temperature; Title compound not separated from byproducts; |
2-{[1-Phenyl-meth-(E)-ylidene]-amino}-pentanoic acid ethyl ester
A
D-norvaline
B
L-Norvaline
Conditions | Yield |
---|---|
With water; chymotrypsin In acetonitrile for 208h; Yield given. Title compound not separated from byproducts; |
DL-norvaline ethyl ester; hydrochloride
L-Norvaline
L-Norvaline
phthalic anhydride
L-Norvaline
(S)-2-(1,3-dioxoisoindolin-2-yl)pentanoic acid
Conditions | Yield |
---|---|
at 135℃; | 100% |
at 140℃; for 0.166667h; | 98% |
With triethylamine In toluene at 130℃; Dean-Stark; | 37% |
at 130℃; |
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 90℃; | 100% |
L-Norvaline
2-Nitrobenzenesulfonyl chloride
2-(2-nitro-benzenesulfonylamino)-pentanoic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; water at 20℃; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water at 3℃; Darkness; | 99% |
L-Norvaline
ethyl trifluoroacetate,
(S)-2-(2,2,2-trifluoroacetamido)pentanoic acid
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With hydrogenchloride Ambient temperature; | 98% |
With hydrogenchloride for 1h; Reflux; | 98% |
With hydrogenchloride for 6h; Reflux; Inert atmosphere; | 97% |
L-Norvaline
trifluoroacetic anhydride
4-propyl-2-(trifluoromethyl)oxazol-5(2H)-one
Conditions | Yield |
---|---|
for 1h; Reflux; | 97% |
L-Norvaline
di-tert-butyl dicarbonate
N-tert-butoxycarbonyl-L-norvaline
Conditions | Yield |
---|---|
Stage #1: L-Norvaline With sodium hydroxide In tetrahydrofuran; water at 0℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 0 - 20℃; for 24h; | 95% |
Stage #1: L-Norvaline With sodium hydroxide In 1,4-dioxane; water for 6h; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 20℃; Cooling with ice; | 69.42% |
With sodium hydroxide In 1,4-dioxane at 20℃; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene Heating / reflux; | 95% |
ethanol
L-Norvaline
toluene-4-sulfonic acid
tosylate de L-norvalinate d'ethyle
Conditions | Yield |
---|---|
In benzene for 10h; Heating; | 94% |
Conditions | Yield |
---|---|
With molecular sieve In ethanol under N2; aq. NaOH added to amino acid, soln. stirred at room temp. for 5 min, soln. concd. under vac., residue dried at 60°C (vac., 16 h), molecular sieves (4 Angstroem), ferrocenecarboxaldehyde and EtOH added, mixt. stirred (room temp., 16 h); molecular sieves filtered off, filtrate concd. under vac., residue suspd. in pentane, solid filtered off, washed with pentane, dried under vac.; | 94% |
L-Norvaline
N-hydroxysuccinimide ester of 7-(1-carboxyethoxy)-4-phenylcoumarin
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1h; Condensation; | 90.9% |
Conditions | Yield |
---|---|
at 0 - 20℃; | 89% |
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 0℃; for 1h; | 88.5% |
With sodium hydroxide In tetrahydrofuran at 0℃; for 1h; | 88.5% |
Conditions | Yield |
---|---|
In methanol for 24h; | 88% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol at 60 - 70℃; diastereoselective reaction; | 88% |
L-Norvaline
4-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indole
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 90℃; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
Stage #1: L-Norvaline; Cyclopentanol at -5℃; for 0.166667h; Cooling with acetone-dry ice; Stage #2: With thionyl chloride at 20 - 60℃; for 42h; | 86% |
Conditions | Yield |
---|---|
With hydrogenchloride | 85% |
With hydrogenchloride Heating; |
L-Norvaline
(S)-2,5-dioxopyrrolidin-1-yl 2-((tert-butoxycarbonyl)amino)butanoate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water; acetone at 20℃; | 84% |
L-Norvaline
2-(S)-hydroxyvaleric acid
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 1h; | 82% |
With hydrogenchloride; acetic acid; sodium nitrite | |
With hydrogenchloride; silver(I) nitrite | |
With hydrogenchloride; acetic acid; sodium nitrite at 0 - 20℃; | |
With sulfuric acid; sodium nitrite In water at 0℃; for 2h; |
L-Norvaline
(2S)-2-chloropentanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite In water at 0℃; | 82% |
With hydrogenchloride; sodium nitrite at -5℃; for 15h; |
Conditions | Yield |
---|---|
With hydrogenchloride In potassium hydroxide; water org. compd. dissoln. in aq. KOH soln., aq. Pt-salt soln. addn., ppt. filtration off, concd. HCl addn. to filtrate, mixt. boiling for ca. 5 min, pptn.; ppt. filtration off, washing (HCl 1:1), drying at 100°C; elem. anal.; | 80% |
Conditions | Yield |
---|---|
With sodium carbonate In 1,4-dioxane; water at 20 - 25℃; for 3h; | 78% |
Conditions | Yield |
---|---|
With sodium hydroxide | 77% |
Stage #1: L-Norvaline; benzyl chloroformate With sodium hydrogencarbonate In water at 0 - 20℃; for 24.75h; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=1; | 73% |
With sodium hydroxide; sodium carbonate In water at 0 - 20℃; | |
With lithium hydroxide In water; toluene at 0 - 20℃; for 15h; |
The IUPAC name of L-Norvaline is (2S)-2-aminopentanoic acid. With the CAS registry number 6600-40-4, it is also named as Pentanoic acid, 2-amino-. The product's categories are Chiral; Protected Amino Acid & Peptides; Norvaline [Nva]; Amino Acids; Unusual Amino Acids; Pharmaceutical Intermediates; Amino Acids. It is white to light yellow crystal powder which is a non-proteinogenic branched-chain amino acid.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.12; (4)ACD/LogD (pH 7.4): -2.12; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.463; (13)Molar Refractivity: 30.27 cm3; (14)Molar Volume: 109.7 cm3; (15)Polarizability: 12×10-24 cm3; (16)Surface Tension: 41.9 dyne/cm; (17)Enthalpy of Vaporization: 50.61 kJ/mol; (18)Vapour Pressure: 0.0366 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 117.078979; (21)MonoIsotopic Mass: 117.078979; (22)Topological Polar Surface Area: 63.3; (23)Heavy Atom Count: 8; (24)Complexity: 82.5; (25)Defined Atom StereoCenter Count: 1.
Preparation of L-Norvaline: It can be obtained by 2-oxo-pentanoic acid anion. This reaction needs reagent pyridoxal phosphate, L-glutamic acid and solvent H2O at temperature of 40 °C. The reaction time is 18 hours and the yield is 32%. The other conditions are E.coli Aspartate transaminase and pH 8.
Uses of L-Norvaline: It is known to promote tissue regeneration and muscle growth and become a precursor in the penicillin biosynthetic pathway. It also can be used for nutrition agent and drug synthesis. For example: it can react with phthalic acid anhydride to get N,N-phthaloyl-L-norvaline. This reaction reacts at 130 °C.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)[C@@H](N)CCC
2. InChI:InChI=1/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
3. InChIKey:SNDPXSYFESPGGJ-BYPYZUCNBD
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