(RS)-tyrosinamide hydrochloride
tyrosine
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate monohydrate In aq. buffer at 40℃; for 6h; pH=8.0; Enzymatic reaction; | 99% |
tyrosine
Conditions | Yield |
---|---|
Stage #1: C15H15N3*C16H13Cl2NO4 With hydrogenchloride In acetonitrile at 20℃; for 1h; Stage #2: With triethylamine In water at 20℃; for 1h; | 90% |
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; |
Conditions | Yield |
---|---|
With D-Alanine; meso-diaminopimelate dehydrogenase; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; alcohol dehydrogenases from Thermoanaerobacter brockii; NADH In isopropyl alcohol at 35℃; for 12h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 62.3% |
Conditions | Yield |
---|---|
With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol In water at 30℃; for 1h; pH=7.3; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | 47% |
durch Einw. von wachsender Hefe in Gegenwart von Malzextrakt oder Hefeautolysat; | |
With oidium lactis |
N-formyl-DL-tyrosine
tyrosine
Conditions | Yield |
---|---|
With water; brucine |
D-tyrosine amide; hydrochloride
tyrosine
Conditions | Yield |
---|---|
With hydrogenchloride |
D-(R)-phenylalanine
A
tyrosine
B
(2R)-2-amino-3-(2-hydroxyphenyl)propanoic acid
C
m-hydroxy-D-phenylalanine
Conditions | Yield |
---|---|
With sulfuric acid; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate at 20 - 50℃; Product distribution; various acid concentration; anaerob condition; | |
With air; 5-ethyl-10-methyl-2,4-dioxo-2,3,4,10-tetrahydrobenzo[g]pteridin-5-ium perchlorate In sulfuric acid at 20℃; Product distribution; Mechanism; hydroxylating ability of the system; other temperatures and acid; other oxidant or without them; |
A
tyrosine
B
2-amino-2-(3,5-dihydroxyphenyl)acetic acid
C
Amino-{3-[4-(amino-carboxy-methyl)-2-chloro-phenoxy]-4-hydroxy-phenyl}-acetic acid
Conditions | Yield |
---|---|
With hydrogenchloride; mercaptoacetic acid at 110℃; for 24h; | A n/a B n/a C n/a D 39 mg |
N-carbamyl-D-tyrosine
tyrosine
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 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; |
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate In water; tert-butyl alcohol at 40℃; for 3h; alcalase, pH=8.5; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
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 pyridoxal 5'-phosphate; ethylenediaminetetraacetic acid; sodium diphenylglycine In aq. buffer at 50℃; pH=8; Overall yield = 9 %; enantioselective reaction; | A n/a B n/a |
Conditions | Yield |
---|---|
With Phen60*Cu(II); PIPES buffer; water at 25℃; for 24h; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With water In tert-butyl alcohol pH=11.5; Hydrolysis; | |
With Streptomyces spp. 82F2 D-aminopeptidase In dimethyl sulfoxide at 20℃; for 0.0833333h; pH=6.5; aq. buffer; Enzymatic reaction; |
A
tyrosine
B
2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
A
tyrosine
B
2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
A
tyrosine
B
2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
Conditions | Yield |
---|---|
With acetone man hydriert das Reaktionsprodukt mit Palladium in Eisessig und verseift das Produkt mit Salzsaeure; |
tyrosine
Conditions | Yield |
---|---|
With potassium hydroxide Erhitzen mit Salzsaeure im Druckrohr auf 100grad; |
tyrosine
Conditions | Yield |
---|---|
With hydrogenchloride |
tyrosine
Conditions | Yield |
---|---|
Hydrolysis; -; |
Conditions | Yield |
---|---|
With aminoacylase I from Aspergillus melleus; Tris buffer In water at 25℃; for 5.5h; pH=6.5; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
at 20℃; under 0 Torr; Kinetics; |
Conditions | Yield |
---|---|
at 20℃; under 0 Torr; Kinetics; |
(R)-sec-butylamine
B
tyrosine
Conditions | Yield |
---|---|
at 20℃; under 0 Torr; Kinetics; |
(R)-sec-butylamine
B
tyrosine
Conditions | Yield |
---|---|
at 20℃; under 0 Torr; Kinetics; |
Conditions | Yield |
---|---|
With meso-2,6-D-diaminopimelic acid dehydrogenase mutant BC621; ammonium chloride; NADPH In various solvent(s) for 24h; | |
With L-glutamic acid; recombinant Pseudomonas stutzeri ST-201 D-phenylglycine aminotransferase; sodium chloride In aq. buffer at 37℃; pH=9.5; Enzymatic reaction; enantioselective reaction; | n/a |
Conditions | Yield |
---|---|
With thionyl chloride Reflux; | 100% |
With thionyl chloride at 0 - 25℃; for 12h; | 95% |
With thionyl chloride at 0 - 10℃; for 0.5h; |
Conditions | Yield |
---|---|
With acetyl chloride | 100% |
With acetyl chloride for 3h; Heating; | 100% |
With thionyl chloride at 0℃; for 16h; | 100% |
di-tert-butyl dicarbonate
tyrosine
N,O-bis(tert-butoxycarbonyl)-D-tyrosine
Conditions | Yield |
---|---|
With sodium hydroxide In water; isopropyl alcohol at 37℃; pH=11.5 - 12; | 100% |
With sodium hydroxide In water; isopropyl alcohol at 37℃; pH=11.5 - 12; |
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 168h; | 100% |
Conditions | Yield |
---|---|
With thionyl chloride In methanol for 5h; Reflux; | 99.7% |
tyrosine
3',5'-dibromo-D-tyrosine hydrobromide
Conditions | Yield |
---|---|
With bromine; acetic acid at 20℃; for 4h; | 98% |
tyrosine
Conditions | Yield |
---|---|
With thionyl chloride; acetic acid at 20℃; for 3h; | 97.5% |
With sulfuryl dichloride; acetic acid at 20℃; for 2h; | 94% |
di-tert-butyl dicarbonate
tyrosine
N-(tert-butoxycarbonyl)-D-tyrosine
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water at 20℃; | 97% |
With sodium hydroxide In 1,4-dioxane at 20℃; for 0.5h; | |
With sodium hydroxide In 1,4-dioxane at 20℃; |
tyrosine
(R)-3,5-bromotyrosine bromate
Conditions | Yield |
---|---|
With bromine In acetic acid at 80℃; for 2h; | 92% |
With bromine; acetic acid at 70℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With sodium carbonate In ethanol boiling; | 90% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h; | 90% |
Conditions | Yield |
---|---|
With thionyl chloride at 95℃; for 12h; | 90% |
tyrosine
N-(tert-butoxycarbonyl)-D-tyrosine
Conditions | Yield |
---|---|
88% | |
Multi-step reaction with 3 steps 1: HCl 2: 95 percent / triethylamine; pyridine / CHCl3; tetrahydrofuran / 10 - 20 °C 3: lithium hydroxide / methanol; H2O / 20 °C View Scheme |
tyrosine
(1S,3E)-5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-1-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-5-oxo-3-pentenyl-(2S)-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoate
N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-tyrosine
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide In N,N-dimethyl-formamide at 55 - 60℃; | 87% |
tyrosine
3-chloro-D-tyrosine
Conditions | Yield |
---|---|
With sulfuryl dichloride; acetic acid at 20℃; | 86% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 20℃; for 8h; | 85% |
With sodium hydroxide In water at 2℃; for 1h; |
tyrosine
Conditions | Yield |
---|---|
With phosphorus pentoxide; phosphoric acid at 80℃; for 24h; | 85% |
With phosphorus pentoxide; phosphoric acid In water at 80℃; for 24h; Inert atmosphere; | 81% |
With phosphorus pentoxide; phosphoric acid at 80℃; Inert atmosphere; | 16% |
With phosphorus pentoxide; phosphoric acid at 80℃; for 24h; |
[(-CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)-)Ni2(μ-Cl)](perchlorate)
tyrosine
Conditions | Yield |
---|---|
Stage #1: [(-CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)CH2C6H2(S)(tert-butyl)CH2N(methyl)C2H4N(methyl)C2H4N(methyl)-)Ni2(μ-Cl)](perchlorate); tyrosine With triethylamine In methanol; acetonitrile for 4h; Inert atmosphere; Schlenk technique; Stage #2: lithium perchlorate trihydrate In methanol; ethanol; acetonitrile at 40℃; for 6h; Inert atmosphere; Schlenk technique; | 84% |
tyrosine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Conditions | Yield |
---|---|
Stage #1: tyrosine; [(Cp)Ru(η6-naphthalene)]CF3SO3 With hydrogenchloride In water for 15h; Irradiation; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In 1,4-dioxane at 0 - 23℃; for 15h; | 84% |
tyrosine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
trifluoroacetic acid
Conditions | Yield |
---|---|
Stage #1: tyrosine; [(Cp)Ru(η6-naphthalene)]CF3SO3 With hydrogenchloride In water for 15h; Irradiation; Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide With sodium carbonate In 1,4-dioxane; water at 0 - 23℃; for 15h; Stage #3: trifluoroacetic acid In water pH=3; | 84% |
tyrosine
Conditions | Yield |
---|---|
With sulfuryl dichloride In acetic acid for 5h; Ambient temperature; | 80% |
With sulfuryl dichloride; acetic acid at 20℃; for 5h; Inert atmosphere; | |
With sulfuryl dichloride; acetic acid at 20℃; for 24h; Inert atmosphere; | |
With sulfuryl dichloride In acetic acid at 20℃; for 16h; |
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; | 80% |
tyrosine
benzyl chloroformate
N-benzyloxycarbonyl-(O-benzyloxycarbonyl)-(R)-tyrosine
Conditions | Yield |
---|---|
In tetrahydrofuran | 78% |
With sodium hydroxide |
tyrosine
benzyl chloride
(R)-2-amino-3-(4-(benzyloxy)phenyl)propanoic acid
Conditions | Yield |
---|---|
Stage #1: tyrosine With potassium hydroxide; copper(II) sulfate In water at 15 - 65℃; for 1h; Stage #2: benzyl chloride In water; N,N-dimethyl-formamide at 20 - 60℃; for 2h; Stage #3: With hydrogenchloride; ammonia more than 3 stages; | 77% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 60 - 80℃; for 1.5h; | 74.5% |
tyrosine
Conditions | Yield |
---|---|
Stage #1: tyrosine With copper(ll) sulfate pentahydrate; 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; potassium carbonate In methanol; water at 20℃; for 5h; Stage #2: 3-trifluoromethylphenyl propargyl sulfide With sodium acetate; copper (I) acetate; sodium L-ascorbate In methanol at 30℃; for 16h; | 73% |
Conditions | Yield |
---|---|
In methanol; water for 24h; Inert atmosphere; Reflux; | 69% |
Molecular Structure:
Molecular Formula: C9H11NO3
Molecular Weight: 181.1885
IUPAC Name: (2R)-2-Amino-3-(4-hydroxyphenyl)propanoic acid
Synonyms of D-Tyrosine (CAS NO.556-02-5): EINECS 209-112-6 ; (R)-(+)-Tyrosine;rarechem ab pp 1343 ; (R)-(+)-3-(4-Hydroxyphenyl)-d-alanine ; (R)-2-Amino-3-(4-hydroxyphenyl)propionic acid;TYROSINE, D- ; 3-(4-Hydroxyphenyl)-d-alanine ; D-3-(4-Hydroxyphenyl)alanine;d(+)-tyrosine
CAS NO: 556-02-5
Product Categories: Amino Acids Derivatives ; AMINO ACIDS ; Tyrosine [Tyr, Y] ; Amino Acids and Derivatives ; alpha-Amino Acids ; Biochemistry ; Amino Acids and Derivatives
Melting point: >300 °C
Index of Refraction: 1.614
Molar Refractivity: 47.37 cm3
Molar Volume: 135.8 cm3
Surface Tension: 65.7 dyne/cm
Density: 1.333 g/cm3
Flash Point: 186.7 °C
Enthalpy of Vaporization: 66.87 kJ/mol
Boiling Point: 385.2 °C at 760 mmHg
Vapour Pressure: 1.27E-06 mmHg at 25°C
D-Tyrosine (CAS NO.556-02-5) is an amino acid synthesized in the body from the essential amino acid phenylalanine. And it has been used to treat sleep disorders, enhance cognitive function, and alleviate symptoms of ADD.
Hazard Codes of D-Tyrosine (CAS NO.556-02-5): Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S24/25: Avoid contact with skin and eyes.
WGK Germany: 3
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