L-isoleucine
Conditions | Yield |
---|---|
With resin bound tetrathiomolybdate In methanol at 28℃; for 1.5h; ultrasonic bath; | 100% |
Fmoc-Ile-OH
L-isoleucine
Conditions | Yield |
---|---|
With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide for 9h; Ambient temperature; | 98% |
N-(tert-butyloxycarbonyl)-L-isoleucine
L-isoleucine
Conditions | Yield |
---|---|
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.166667h; Ionic liquid; | 98% |
With trifluoroacetic acid at 20℃; for 0.25h; |
L-isoleucine
Conditions | Yield |
---|---|
With dimethyl ether-poly(hydrogen fluoride) at 0℃; for 1h; | 93% |
A
3,3-dimethyloxindole
B
1,3-dihydro-3,3-dimethyl-1-hydroxy-H-indol-2-one
C
L-isoleucine
Conditions | Yield |
---|---|
With hydrogen; acetic acid; palladium on activated charcoal In methanol for 0.5h; | A n/a B n/a C 85% |
(S)-4-((S)-sec-butyl)oxazolidine-2,5-dione
L-Glycin
A
L-isoleucine
B
isoleucyl‐glycine
C
N-carbamoylglycine
Conditions | Yield |
---|---|
With water; potassium hydroxide; potassium borate buffer at 3℃; Product distribution; effect of use of various amino acid and NCA with various concentrations; effect of use various temp.; extent of hydrolysis; | A n/a B 83.9% C n/a D n/a |
L-isoleucine
Conditions | Yield |
---|---|
With ruthenium nanoparticles dispersed in a polyvinylpyrrolidone matrix; amberlyst A-21 In methanol; dichloromethane | 75% |
(2S,3S)-3-methyl-2-ureidopentanoic acid
L-isoleucine
Conditions | Yield |
---|---|
With NH4Cl-NH4OH buffer pH 8.5; nickel dichloride at 60℃; for 24h; N-carbamyl-L-amino acid aminohydrolase; | 55% |
With sodium phosphate buffer; N-carmamyl-L-amino acid aminohydrolase of Pseudomonas sp. strain NS671; water; manganese(II) at 30℃; for 0.5h; Product distribution; | 17.1 mmol |
With Tris-HCl buffer; N-carbamoyl-L-amino acid hydrolase; iron(II) sulfate at 30℃; for 2h; |
B
L-isoleucine
Conditions | Yield |
---|---|
With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; formate dehydrogenase; phenylalanine dehydrogenase In water at 30℃; for 24h; | A 50% B 48% |
Conditions | Yield |
---|---|
With C13H15NO5V(1-)*C16H36N(1+) In ethanol; water | A n/a B 50% |
With C13H15NO5V(1-)*C16H36N(1+) In ethanol; water | A 24% B n/a |
L-isoleucine
Conditions | Yield |
---|---|
With hydrogenchloride; Dowex 50W In toluene at 110℃; | 34% |
Conditions | Yield |
---|---|
With Escherichia coli TVD5 at 37℃; for 24h; biotransformation; Microbiological reaction; | 25.5% |
di-tert-butyl dicarbonate
N-chloro-(2S,3S)-amino-3-methyl-pentanoic acid ethyl ester
A
L-isoleucine
B
(2S,3S)-1-tert-butyl 2-ethyl 3-methyl-pyrrolidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Stage #1: N-chloro-(2S,3S)-amino-3-methyl-pentanoic acid ethyl ester With sulfuric acid at 3 - 9℃; for 3h; UV-irradiation; Stage #2: di-tert-butyl dicarbonate With potassium carbonate In 1,4-dioxane; water at 0 - 20℃; Further stages.; | A n/a B 25% |
hydrogen cyanide
(S)-2-methylbutyraldehyde
A
L-isoleucine
B
D-alloisoleucine
Conditions | Yield |
---|---|
With ammonia durch Verseifung des entstandenen Aminonitrils mit Salzsaeure; |
L-isoleucine
Conditions | Yield |
---|---|
durch gaerende Hefe; | |
With D-amino acid oxide ase-substances Durch selektiven Abbau; |
L-isoleucine
Conditions | Yield |
---|---|
fuehrt man dieses in Formyl-dl-isoleucin ueber und zerlegt letzteres in konz. alkoh. Loesung durch Brucin in die aktiven Komponenten; |
N-formyl-L-isoleucine
L-isoleucine
Conditions | Yield |
---|---|
With hydrogen bromide |
N-chloroacetyl-isoleucine
L-isoleucine
Conditions | Yield |
---|---|
With acylase-I-substances Hydrolysis; |
N-chloroacetyl-DL-isoleucine
A
L-isoleucine
B
N-chloroacetyl-D-isoleucine
Conditions | Yield |
---|---|
bei der Einwirkung von Acylase-I-Praeparaten aus Schweinenieren; |
L-isoleucine
Conditions | Yield |
---|---|
With hydrogenchloride |
D-Glucose
A
L-isoleucine
B
L-glutamic acid
C
L-Lysine hydrochloride
D
L-tyrosine
Conditions | Yield |
---|---|
at 30℃; for 72h; Brevibacterium flavum, mutant strain AH-198, soybean-meal hydrolysate, (NH4)2SO4; Yield given. Further byproducts given. Yields of byproduct given; |
(S)-1-phenyl-ethylamine
A
D-allo-isoleucine
B
L-isoleucine
C
D-Isoleucine
D
D-alloisoleucine
Conditions | Yield |
---|---|
Product distribution; Rate constant; multistep reaction; |
(2S,3S)-2-Amino-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-pentan-1-one
L-isoleucine
Conditions | Yield |
---|---|
With lithium hydroxide; ion exchange 1.) THF; Yield given. Multistep reaction; |
carbon monoxide
A
L-serin
B
L-threonine
C
L-isoleucine
D
L-Aspartic acid
Conditions | Yield |
---|---|
With sodium molybdate; ammonium iron (II) sulfate; water; sodium carbonate; ammonium chloride; calcium chloride; magnesium chloride; zinc(II) chloride for 5h; Ambient temperature; Irradiation; pH=7.0; Further byproducts given; |
(2S,3S)-2-{[1-(3-Hydroxy-2-methyl-5-phosphonooxymethyl-pyridin-4-yl)-meth-(Z)-ylidene]-amino}-3-methyl-pentanoic acid
A
L-isoleucine
B
pyridoxal 5'-phosphate
Conditions | Yield |
---|---|
In water at 25℃; Equilibrium constant; Mechanism; over a wide pH range; | |
With phosphate buffer; Carbonate buffer at 25℃; Equilibrium constant; var. pH; |
(2S,3R)-2-Azido-3-methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
A
D-allo-isoleucine
B
L-isoleucine
C
D-Isoleucine
D
D-alloisoleucine
Conditions | Yield |
---|---|
With titanium tetrakis(benzyl alkoxide); hydrogen; Pd-BaSO4 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t.; Yield given. Multistep reaction. Title compound not separated from byproducts; |
N-(S)-2-methylbutylformamide
A
L-isoleucine
B
D-alloisoleucine
Conditions | Yield |
---|---|
With hydrogenchloride; Dowex 50(H+) at 100 - 110℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
N-((S)-1-Cyano-2-methyl-butyl)-acetamide
A
L-isoleucine
B
D-alloisoleucine
Conditions | Yield |
---|---|
With hydrogenchloride; Dowex 50(H+) at 100 - 110℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With hydrogenchloride; Dowex 50(H+) at 100 - 110℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
Stage #1: methanol With thionyl chloride at -15 - 0℃; for 1h; Stage #2: L-isoleucine for 3h; Reflux; | 100% |
With hydrogenchloride | 96% |
With thionyl chloride at 0℃; for 12h; Reflux; | 95% |
Conditions | Yield |
---|---|
With thionyl chloride for 38h; Heating; | 100% |
With thionyl chloride | 100% |
With thionyl chloride for 10h; Heating; | 65% |
L-isoleucine
di-tert-butyl dicarbonate
N-(tert-butyloxycarbonyl)-L-isoleucine
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 24h; | 100% |
Stage #1: L-isoleucine With sodium hydroxide In 1,4-dioxane; water at 0℃; Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃; | 100% |
With sodium hydroxide In 1,4-dioxane; water at 0℃; | 100% |
Conditions | Yield |
---|---|
at 135℃; | 100% |
at 140℃; for 0.166667h; | 99% |
With triethylamine Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 20℃; | 100% |
With sodium hydroxide In 1,4-dioxane; toluene at 0℃; | 97% |
With water; sodium hydrogencarbonate; sodium carbonate In acetone at 15 - 20℃; pH=8 - 10; | 95% |
L-isoleucine
1,4,5,8-naphthalenetetracarboxylic dianhydride
2,2'-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydrobenzo[lmn][3,8]phenanthroline-2,7-diyl)bis(3-methylpentanoic acid)
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 110℃; for 24h; | 100% |
With acetic acid for 36h; Reflux; | 89% |
Conditions | Yield |
---|---|
With lithium hydride In methanol Reflux; | 100% |
Conditions | Yield |
---|---|
With sodium methylate In methanol Reflux; | 100% |
Conditions | Yield |
---|---|
With caesium carbonate In methanol Reflux; | 100% |
Conditions | Yield |
---|---|
With calcium hydride In methanol Reflux; | 100% |
L-isoleucine
5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde
Conditions | Yield |
---|---|
With lithium hydride In methanol Reflux; | 100% |
L-isoleucine
5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde
Conditions | Yield |
---|---|
With sodium methylate In methanol Reflux; | 100% |
L-isoleucine
5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde
Conditions | Yield |
---|---|
With caesium carbonate In methanol Reflux; | 100% |
L-isoleucine
5-(4-methylphenyl)-1,2-oxazole-3-carbaldehyde
Conditions | Yield |
---|---|
With calcium hydride In methanol Reflux; | 100% |
L-isoleucine
bis(trichloromethyl) carbonate
(S)-4-((S)-sec-butyl)oxazolidine-2,5-dione
Conditions | Yield |
---|---|
In tetrahydrofuran at 50℃; for 4.5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 2.3 - 3.3; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
With acetyl chloride for 18h; Reflux; | 99% |
With hydrogenchloride Ambient temperature; | 98% |
Stage #1: methanol With thionyl chloride at 0℃; for 0.5h; Stage #2: L-isoleucine In methanol at 0℃; | 97.5% |
L-isoleucine
(2S,3S)-2-Hydroxy-3-methylpentanoic acid
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite In water at 0 - 20℃; | 99% |
With sulfuric acid; sodium nitrite at 0 - 20℃; for 18h; | 92% |
With sulfuric acid; water; sodium nitrite at 60℃; Flow reactor; | 92% |
L-isoleucine
(2S,3S)-2-azido-3-methylpentanoic acid
Conditions | Yield |
---|---|
With sodium azide; copper(ll) sulfate pentahydrate; trifluoromethylsulfonic anhydride; potassium carbonate In methanol; dichloromethane; water at 0 - 20℃; for 16h; | 99% |
With sodium azide; trifluoromethylsulfonic anhydride; copper sulfate pentahydrate; potassium carbonate In dichloromethane; water at 20℃; for 16h; | 99% |
With sodium azide; copper(ll) sulfate pentahydrate; trifluoromethylsulfonic anhydride; potassium carbonate In dichloromethane; water at 0 - 20℃; for 16h; | 99% |
L-isoleucine
4-(phenylacetoxy)benzyl-L-phenylalanine
Conditions | Yield |
---|---|
With HEPES-buffer; calcium chloride; thermolysin In ethyl acetate at 40℃; for 48h; pH=6.5; | 99% |
L-isoleucine
tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester
Boc-Ala-Ile-OH
Conditions | Yield |
---|---|
Stage #1: L-isoleucine With calcium hydroxide In water at 20℃; Stage #2: tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester In N,N-dimethyl-formamide at 25℃; for 24h; | 99% |
L-leucine
L-isoleucine
malonic acid
L-valinal
(Ac)-NSLKIDNLDV-CONH2
Conditions | Yield |
---|---|
Stage #1: L-valinal With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Stage #2: With piperidine for 0.333333h; Microwave irradiation; Stage #3: L-leucine; L-isoleucine; malonic acid; Fmoc-Asn(PG)-OH; Fmoc-Ser(PG)-OH; Fmoc-Lys(PG)-OH; Fmoc-Asp(PG)-OH Further stages; | 99% |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; potassium carbonate In methanol; water at 20℃; for 16h; | 99% |
With copper(ll) sulfate pentahydrate; potassium carbonate In methanol; dichloromethane; water at 20℃; | 75% |
Conditions | Yield |
---|---|
Stage #1: pyridine-4-carbaldehyde; L-isoleucine With sodium carbonate In water at 60℃; for 3h; Stage #2: With sodium tetrahydroborate In water at 0℃; | 98.15% |
L-isoleucine
p-toluenesulfonyl chloride
3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}pentanoic acid
Conditions | Yield |
---|---|
In water at 110℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction; | 98% |
With sodium carbonate In water for 5h; | 95.74% |
With sodium carbonate In water for 4h; | 95.74% |
L-isoleucine
4-(phenylacetoxy)benzyl-L-methionine
Conditions | Yield |
---|---|
With HEPES-buffer; calcium chloride; thermolysin In ethyl acetate at 40℃; for 24h; pH=6.5; | 98% |
L-isoleucine
(+)-(S)-2-methylbutane nitrile
Conditions | Yield |
---|---|
With sodium hydroxide; trichloroisocyanuric acid at 25℃; for 0.5h; | 98% |
With trichloroisocyanuric acid; sodium hydrogencarbonate In water at 5 - 15℃; for 3.25h; | 93.2% |
With ammonium bromide In methanol; water Electrochemical reaction; | 86% |
L-isoleucine
5-(1-carboxy-2-methyl-butylamino)-3-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester
Conditions | Yield |
---|---|
In methanol at 60℃; | 98% |
Reported in EPA TSCA Inventory.
Isoleucine is an α-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)CH2CH3. With the CAS NO.73-32-5, it also called (2S,3S)-2-Amino-3-methylpentansαure; (2s,3s)-alpha-amino-beta-merthylvalericacid; (2s,3s)-alpha-amino-beta-methyl-n-valericacid; (s-(r*,r*))-2-amino-3-methylpentanoicaci; (s-(r*,r*))-2-amino-3-methylpentanoicacid; (S,S)-2-amino-3-methyl-pentanoicacid; (s,s)-isoleucine; [S-(R*,R*)]-2-Amino-3-methylpentanoic acid. And it is a white crystals or crystalline solid. Isoleucine can be used in biochemical research, and in medicine used for nutritional supplements.
Physical properties about Isoleucine are: (1)ACD/LogP: 0.799; (2)ACD/LogD (pH 5.5): -1.70; (3)ACD/LogD (pH 7.4): -1.70; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.463; (12)Molar Refractivity: 34.863 cm3; (13)Molar Volume: 126.632 cm3; (14)Polarizability: 13.821 10-24cm3; (15)Surface Tension: 39.0019989013672 dyne/cm; (16)Density: 1.036 g/cm3; (17)Flash Point: 90.344 °C; (18)Enthalpy of Vaporization: 50.93 kJ/mol; (19)Boiling Point: 225.772 °C at 760 mmHg; (20)Vapour Pressure: 0.0309999994933605 mmHg at 25°C
Preparation of Isoleucine: Isoleucine(CAS NO.73-32-5) can be produced with sugar, ammonia, D-threonine as raw material.Serratia spp race (Serratia marcescens) fermentation derived. Or with sugar, ammonia, α-amino butyric acid as raw material.And it derived from yellow cocci (Micrococcus flavum), or Bacillus subtilis (Bacillus subtilis; Aerobactor) fermentation.
When you are using this chemical, please be cautious about it as the following:
1. Avoid contact with skin and eyes
2. Wear suitable protective clothing
3. Do not breathe dust
You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1;
(2)InChIKey=AGPKZVBTJJNPAG-WHFBIAKZSA-N;
(3)SmilesC([C@H]([C@H](CC)C)N)(O)=O;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | intraperitoneal | 6822mg/kg (6822mg/kg) | Archives of Biochemistry and Biophysics. Vol. 58, Pg. 253, 1955. | |
rat | LD50 | intraperitoneal | 6822mg/kg (6822mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archives of Biochemistry and Biophysics. Vol. 58, Pg. 253, 1955. |
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