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| CAS No.: | 6600-40-4 |
|---|---|
| Name: | L-norvaline |
| Article Data: | 64 |
| Molecular Structure: | |
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| Formula: | C5H11NO2 |
| Molecular Weight: | 117.148 |
| Synonyms: | L-Norvaline (9CI);Norvaline, L-;L-2-Aminovaleric acid;L-2-aminopentanoate;(S)-2-Aminopentanoic acid;L-(+)-2-aminovaleric acid;L-2-aminopentanoic acid;(2S)-2-aminopentanoic acid;alpha-L-Aminopentanoic acid;Leucine,2-methyl-;Pentanoic acid, 2-amino-, (S)-;L-Norvaaline;L(+)-Norvaline;(S)-2-Amino-pentanoic acid; |
| EINECS: | 229-543-3 |
| Density: | 1.067 g/cm3 |
| Melting Point: | >300 °C(lit.) |
| Boiling Point: | 222.9 °C at 760 mmHg |
| Flash Point: | 88.6 °C |
| Solubility: | 10.5 g/100 mL (18 °C) in water |
| Appearance: | white to light yellow crystal powder |
| Hazard Symbols: |
 C,  Xn
|
| Risk Codes: | 20/21/22-36/37/38 |
| Safety: | 24/25-37/39-26 |
| PSA: | 63.32000 |
| LogP: | 0.89870 |
| 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 |
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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.
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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.
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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
