Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; | 100% |
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.; | 100% |
With dimethylsulfide; hydrogen fluoride at 0℃; for 2h; Product distribution; Var.: HF in anisole; | 99.5% |
Conditions | Yield |
---|---|
With ammonium bicarbonate; water In dichloromethane for 15h; α-chymotrypsin; | 100% |
at 25℃; for 0.833333h; enzyme alcalase from Bacillus licheniforms; pH 8.2; | |
With water at 37℃; Rate constant; pH 7.4; apparent rate constant of product formation; calculated nasal absorption rate constant; | |
With water; sodium chloride In dimethyl sulfoxide at 37℃; Rate constant; also human plasma as reagent; | |
Multi-step reaction with 4 steps 1: dichloromethane / 20 °C 2: copper diacetate; oxygen / acetonitrile / 20 h 3: potassium hydroxide / methanol; water / 7 h / Reflux 4: dimethyl sulfoxide; aq. phosphate buffer / 24 h / 37 °C / pH 7.4 View Scheme |
Conditions | Yield |
---|---|
With ammonium bicarbonate; water In dichloromethane for 12h; α-chymotrypsin; | 100% |
With water at 37℃; Rate constant; pH 7.4; apparent rate constant of product formation; calculated nasal absorption rate constant; | |
With water; sodium chloride In dimethyl sulfoxide at 37℃; Rate constant; also human plasma as reagent; |
N,O-bis-allyloxycarbonyl-L-tyrosine
L-tyrosine
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; acetic acid In dichloromethane Product distribution; slectivity of cleavge of allyl and allyloxycarbonyl groups; other amino acid derivatives; | 100% |
With tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride In dichloromethane Ambient temperature; | 95% |
N-tert-butoxycarbonyl-O-2,6-dichlorobenzyl-L-tyrosine
L-tyrosine
Conditions | Yield |
---|---|
With Nafion H; dimethylsulfide; 3-methyl-phenol; trifluoroacetic acid for 3h; | 100% |
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; | 100% |
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.; | 100% |
Conditions | Yield |
---|---|
With water at 170℃; for 0.05h; Microwave irradiation; | 100% |
With sodium tetrahydroborate In methanol; aq. phosphate buffer at 20℃; for 1h; Cooling with ice; Sealed tube; | 87% |
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 72 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 24 h / 20 °C 3: acetonitrile / 2.6 h / pH 7.2 / Photolysis; HEPES buffer View Scheme |
Conditions | Yield |
---|---|
With formate dehydrogenase; NAD; ammonium formate at 30℃; for 24h; PheDH; | 99% |
With L-phenylalanine; L-specific transaminase ywfG at 20℃; for 16h; pH=8; aq. potassium phosphate buffer; Enzymatic reaction; |
Conditions | Yield |
---|---|
With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; formate dehydrogenase; phenylalanine dehydrogenase In water at 30℃; for 24h; | 99% |
With L-glutamic acid; pyridoxal 5'-phosphate In water at 40℃; for 4h; E.coli Aspartate transaminase, pH 8; | 80% |
(RS)-tyrosinamide hydrochloride
L-tyrosine
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride In aq. buffer at 40℃; for 6h; pH=7.0; Enzymatic reaction; | 99% |
(Z)-2-benzamido-3-(p-hydroxyphenyl)-2-propenic acid
L-tyrosine
Conditions | Yield |
---|---|
With hydrogen; PF6 In tetrahydrofuran at 25℃; under 760 Torr; | 98% |
With hydrogen; PF6 In tetrahydrofuran at 25℃; under 760 Torr; effects of solvents dependency of the optical yields; |
Nα-(allyloxycarbonyl)tyrosine O-allyl ether
L-tyrosine
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride In dichloromethane Ambient temperature; | 95% |
D,L-Tyr-OPron
L-tyrosine
Conditions | Yield |
---|---|
With Alcalase; pyridoxal 5'-phosphate; water In tert-butyl alcohol at 40℃; for 4h; pH=8.5; racemization of D-enantiomer; kin. resolution; | 95% |
benzyl tyrosinate
L-tyrosine
Conditions | Yield |
---|---|
With Alcalase; pyridoxal 5'-phosphate; water In tert-butyl alcohol at 40℃; for 3h; pH=8.5; racemization of D-enantiomer; kin. resolution; | 95% |
With Alcalase; 3,5-dichlorobenzaldehyde In water; acetonitrile at 35℃; for 24h; pH=8.5; Enzymatic reaction; optical yield given as %ee; | 95% |
L-tyrosine
Conditions | Yield |
---|---|
With tris[(3-sulfophenyl)phosphine]palladium(0) dodecasodium salt In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 0.0833333h; pH=7.8; Catalytic behavior; Reagent/catalyst; | 95% |
tyrosine ethyl ester
L-tyrosine
Conditions | Yield |
---|---|
With Alcalase; 3,5-dichlorobenzaldehyde In water; acetonitrile at 35℃; for 72h; pH=7.5; Enzymatic reaction; optical yield given as %ee; | 92% |
With α-chymotrypsin In water; acetone at 30℃; for 24h; Product distribution; var. solvents; other amino acids; | 50% |
D,L-TyrO-iPr
L-tyrosine
Conditions | Yield |
---|---|
With Alcalase; 3,5-dichlorobenzaldehyde In water; acetonitrile at 35℃; for 120h; pH=8.0; Enzymatic reaction; optical yield given as %ee; | 92% |
hexan-1-amine
(S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-3-(4-hydroxy-phenyl)-propionic acid
A
L-tyrosine
B
1-hexyl-3,5-dinitro-4-pyridone
Conditions | Yield |
---|---|
In pyridine Product distribution; | A 88.3% B n/a |
tyrosine methyl ester hydrochloride
A
tyrosine
B
D-tyrosine methyl ester
C
L-tyrosine
Conditions | Yield |
---|---|
at 30℃; for 0.333333h; enzyme alcalase from Bacillus licheniforms; pH 8.0; Yields of byproduct given; | A n/a B 86% C n/a |
at 30℃; for 0.333333h; enzyme alcalase from Bacillus licheniforms; pH 8.0; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
p-borono-L-phenylalanine
L-tyrosine
Conditions | Yield |
---|---|
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation; | 85% |
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; pyridoxal 5'-phosphate; Ammonium; recombinant wild-type thermophilic tyrosine phenol lyases from thermophilic microorganism Symbiobacterium toebii In aq. phosphate buffer at 37℃; pH=8; Green chemistry; Enzymatic reaction; stereoselective reaction; | 84% |
With ammonium chloride at 50℃; β-tyrosinase from Symbiobacterium thermophilum, 0.2 mM pyridoxal-5'-phosphate, 50 mM potassium phosphate buffer pH 8.0; |
(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate
L-tyrosine
Conditions | Yield |
---|---|
With acetic acid In water at 160℃; for 0.0833333h; Microwave irradiation; optical yield given as %ee; | 81% |
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 21 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0 - 21 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: water / 24 h / 21 °C / pH 7.5 View Scheme |
Conditions | Yield |
---|---|
With ammonium acetate In water at 37℃; for 20h; pH 8.5; with Erwinia herbicola; | 80% |
at 70℃; for 2.5h; β-tyrosinase from Symbiobacterium thermophilum, 50 mM potassium phosphate buffer pH 8.0; |
L-tyrosine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 20℃; for 0.5h; Inert atmosphere; | 80% |
methanol
(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid
A
benzyl methyl ether
B
L-tyrosine
Conditions | Yield |
---|---|
With potassium hydroxide; [bis(acetoxy)iodo]benzene at 0 - 5℃; for 1.5h; | A 78% B n/a |
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at 25℃; for 0.333333h; | 72% |
With cell extract of Sphingomonas paucimobilis SC 16113 In water at 42℃; for 20h; Enzymatic reaction; | 100 % Chromat. |
With ethylenediaminetetraacetic acid; phenylmethylsulphonyl fluoride; water In aq. phosphate buffer at 30℃; Kinetics; Reagent/catalyst; Microbiological reaction; Enzymatic reaction; |
tyrosine methyl ester
Moz-Asp(Bzl)-OBzl
A
L-tyrosine
Conditions | Yield |
---|---|
Stage #1: tyrosine methyl ester With Alcalase; water In tert-butyl alcohol at 25℃; pH=8.5; kinetic resolution; Stage #2: Moz-Asp(Bzl)-OBzl With Alcalase In tert-butyl alcohol Condensation; | A n/a B 63% |
D,L-tyrosine benzyl ester hydrochloride
L-tyrosine
Conditions | Yield |
---|---|
Stage #1: D,L-tyrosine benzyl ester hydrochloride With lithium carbonate In water; tert-butyl alcohol at 23℃; for 0.166667h; Resolution of racemate; Stage #2: With 2-Hydroxymethylpyridine; Alcalase; water; zinc(II) acetate dihydrate In tert-butyl alcohol at 23℃; for 4h; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; | 63% |
(S)-3-benzyloxycarbonyl-4-(4-hydroxyphenyl)methyloxazolidin-5-one
L-tyrosine
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at 25℃; for 0.333333h; | 62% |
L-tyrosine
Conditions | Yield |
---|---|
With tris[(3-sulfophenyl)phosphine]palladium(0) dodecasodium salt In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 0.0833333h; pH=7.8; Catalytic behavior; Reagent/catalyst; | 47% |
Conditions | Yield |
---|---|
With thionyl chloride 1.) room temperature, 2 h, 2.) reflux, 0.5 h; | 100% |
With thionyl chloride | 100% |
With thionyl chloride at 0 - 20℃; | 99% |
Conditions | Yield |
---|---|
With hydrogenchloride | 100% |
With sulfuric acid at -10℃; Reflux; | 90.2% |
With amberlyst-15 Ambient temperature; | 70% |
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 168h; | 100% |
With potassium methanolate In methanol at 40℃; | 86% |
With methanol; ion-exchange resin + form>; N,N,N',N'-tetramethylguanidine |
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 4h; Inert atmosphere; Cooling with ice; | 100% |
With N-ethyl-N,N-diisopropylamine | 96% |
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 12h; Cooling with ice; | 95% |
methanol
di-tert-butyl dicarbonate
L-tyrosine
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester
Conditions | Yield |
---|---|
Stage #1: methanol; L-tyrosine With thionyl chloride for 3h; Inert atmosphere; Heating; Stage #2: di-tert-butyl dicarbonate With triethylamine In methanol for 20h; Inert atmosphere; | 100% |
Stage #1: methanol; L-tyrosine With thionyl chloride Heating; Stage #2: di-tert-butyl dicarbonate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; Further stages.; |
L-leucine
L-phenylalanine
L-tyrosine
glycine
H-Tyr-Gly-Gly-Phe-Leu-NH2
Conditions | Yield |
---|---|
Stage #1: L-tyrosine With BF4(1-)*C7H13N3Pol(1+); benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 25℃; for 1h; Ionic liquid; Automated synthesizer; solid phase reaction; Stage #2: glycine In 1-methyl-pyrrolidin-2-one at 25℃; for 1h; Ionic liquid; Automated synthesizer; solid phase reaction; Stage #3: L-leucine; L-phenylalanine Further stages; | 100% |
Conditions | Yield |
---|---|
With tyrosine prenyltransferase SirD from Leptosphaeria maculans; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 1.5h; pH=7.5; Reagent/catalyst; Enzymatic reaction; | 100% |
With 7-dimethylallyl tryptophan synthase from Aspergillus fumigatus; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 16h; pH=7.5; Kinetics; Enzymatic reaction; stereoselective reaction; | 36% |
With potassium chloride; magnesium chloride In aq. buffer at 35℃; for 16h; pH=7.5; Kinetics; | |
With recombinant N-1‑dimethylallyltryptophan synthase from Fusarium f ujikuroi at 35℃; pH=7 - 9; Kinetics; Enzymatic reaction; regiospecific reaction; |
Conditions | Yield |
---|---|
In methanol at 120℃; for 0.25h; Microwave irradiation; | 99.28% |
L-tyrosine
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20℃; for 24h; Inert atmosphere; Schlenk technique; Darkness; | 99.2% |
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h; | 99% |
at 300 - 340℃; | |
Bestrahlen der Kristalle mit Roentgen-Strahlen; |
L-tyrosine
methyl chloroformate
(S)-3-(4-hydroxyphenyl)-2-[(methoxycarbonyl)amino] propionic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; | 99% |
With sodium hydroxide In water at 5℃; for 1.5h; Schotten-Baumann reaction; | 90% |
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; | 80% |
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; |
L-tyrosine
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; ammonia In methanol at 0 - 20℃; for 2h; Inert atmosphere; | 99% |
L-tyrosine
acetyl chloride
(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride
Conditions | Yield |
---|---|
With aluminium trichloride In nitrobenzene at 100℃; for 6h; | 98% |
Stage #1: L-tyrosine With aluminum (III) chloride In nitrobenzene at 20℃; for 0.166667h; Stage #2: acetyl chloride In nitrobenzene at 100℃; for 6h; | 83% |
With aluminium trichloride In nitrobenzene at 100℃; Friedel-Crafts acetylation; | 80% |
1. Introduction of L-Tyrosine
L-Tyrosine, with the IUPAC Name of (2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid, is one kind of white to off-white powder. For being stable in normal condition, it is incompatible with strong oxidizing agents, strong reducing agents. And it belongs to the Product Categories which include Food and Feed Additive;Tyrosine [Tyr, Y];Amino Acids;Amino Acids and Derivatives;alpha-Amino Acids;Biochemistry;Nutritional Supplements;L-Amino Acids;Amino Acids.
2. Properties of L-Tyrosine
L-Tyrosine has the following property datas: (1)Index of Refraction: 1.614; (2)Molar Refractivity: 47.37 cm3; (3)Molar Volume: 135.8 cm3; (4)Polarizability: 18.78×10-24cm3; (5)Surface Tension: 65.7 dyne/cm; (6)Density: 1.333 g/cm3; (7)Flash Point: 186.7 °C; (8)Enthalpy of Vaporization: 66.87 kJ/mol; (9)Melting Point: >300 °C (dec.)(lit.); (10)Boiling Point: 385.2 °C at 760 mmHg; (11)Vapour Pressure: 1.27E-06 mmHg at 25°C; (12)Water Solubility: 0.45 g/L (25 oC).
3. Structure Descriptors of L-Tyrosine
You could convert the following datas into the molecular structure:
(1).InChI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1
(2).InChIKey: InChIKey=OUYCCCASQSFEME-QMMMGPOBSA-N
(3).Smiles: C([C@H](Cc1ccc(O)cc1)N)(O)=O
4. Toxicity of L-Tyrosine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 1450mg/kg (1450mg/kg) | Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 1117, 1977. |
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