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150-30-1 Usage

General Description

DL-3-Phenylalanine is a chemical compound that consists of a phenylalanine molecule with a chiral center at the alpha carbon, resulting in two enantiomers, D-phenylalanine and L-phenylalanine. Phenylalanine is an essential amino acid and is an important building block of proteins in the human body. DL-3-Phenylalanine is commonly used in pharmaceuticals and as a nutritional supplement. It has been studied for its potential health benefits, including its role in the production of neurotransmitters and its ability to inhibit the enzymes responsible for the breakdown of endorphins and enkephalins, which may have analgesic effects. Additionally, DL-3-Phenylalanine has been investigated for its potential use in the treatment of certain mood disorders and chronic pain conditions. Overall, DL-3-Phenylalanine plays a critical role in various physiological processes and has applications in the fields of medicine and nutrition.

Check Digit Verification of cas no

The CAS Registry Mumber 150-30-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 0 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 150-30:
(5*1)+(4*5)+(3*0)+(2*3)+(1*0)=31
31 % 10 = 1
So 150-30-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m1/s1

150-30-1 Well-known Company Product Price

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  • TCI America

  • (P0136)  DL-Phenylalanine  >98.0%(HPLC)(T)

  • 150-30-1

  • 25g

  • 175.00CNY

  • Detail
  • TCI America

  • (P0136)  DL-Phenylalanine  >98.0%(HPLC)(T)

  • 150-30-1

  • 250g

  • 790.00CNY

  • Detail
  • Alfa Aesar

  • (A10132)  DL-Phenylalanine, 99%   

  • 150-30-1

  • 25g

  • 211.0CNY

  • Detail
  • Alfa Aesar

  • (A10132)  DL-Phenylalanine, 99%   

  • 150-30-1

  • 100g

  • 585.0CNY

  • Detail
  • Alfa Aesar

  • (A10132)  DL-Phenylalanine, 99%   

  • 150-30-1

  • 500g

  • 2852.0CNY

  • Detail
  • Vetec

  • (V900615)  DL-Phenylalanine  Vetec reagent grade, 98%

  • 150-30-1

  • V900615-100G

  • 264.42CNY

  • Detail
  • Vetec

  • (V900615)  DL-Phenylalanine  Vetec reagent grade, 98%

  • 150-30-1

  • V900615-500G

  • 842.40CNY

  • Detail
  • Aldrich

  • (147966)  DL-Phenylalanine  ReagentPlus®, 99%

  • 150-30-1

  • 147966-25G

  • 320.58CNY

  • Detail
  • Aldrich

  • (147966)  DL-Phenylalanine  ReagentPlus®, 99%

  • 150-30-1

  • 147966-100G

  • 544.05CNY

  • Detail

150-30-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name phenylalanine

1.2 Other means of identification

Product number -
Other names DL-Phenylalanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:150-30-1 SDS

150-30-1Synthetic route

2-(N-acetylamino)-2-benzylpropanedioic diethyl ester
3235-26-5

2-(N-acetylamino)-2-benzylpropanedioic diethyl ester

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; water at 90℃; for 0.166667h; Microwave irradiation;98%
With water; hydrogen cation Heating;82%
With hydrogen bromide anschliessend Erwaermen mit wss. Schwefelsaeure;
With sodium hydroxide anschliessend Erwaermen mit wss. Schwefelsaeure;
With hydrogenchloride In water at 110℃; Microwave irradiation;
L-phenylalanine
63-91-2

L-phenylalanine

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
salicylaldehyde In acetic acid at 100℃; for 1h;94%
With barium dihydroxide; water at 155 - 160℃;
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times;
benzyl bromide
100-39-0

benzyl bromide

C21H15N3O3(2-)*Ni(2+)

C21H15N3O3(2-)*Ni(2+)

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With potassium hydroxide; C-7 In dichloromethane at 20℃;90%
2-(Benzhydryl-amino)-3-phenyl-propionic acid tert-butyl ester
126181-40-6

2-(Benzhydryl-amino)-3-phenyl-propionic acid tert-butyl ester

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
palladium on activated charcoal In acetic acid Heating;89%
Multi-step reaction with 2 steps
1: 60 percent / formic acid / 10percent Pd/C / methanol
2: trifluoroacetic acid
View Scheme
2-Benzyl-2-benzyloxycarbonylamino-malonic acid dimethyl ester

2-Benzyl-2-benzyloxycarbonylamino-malonic acid dimethyl ester

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With water; hydrogen cation Heating;88%
2-[2-Benzoylamino-1-methoxy-eth-(Z)-ylideneamino]-3-phenyl-propionic acid

2-[2-Benzoylamino-1-methoxy-eth-(Z)-ylideneamino]-3-phenyl-propionic acid

A

Phenylalanine
150-30-1

Phenylalanine

B

methyl hippurate
1205-08-9

methyl hippurate

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether Yields of byproduct given;A n/a
B 69%
2-[2-Benzoylamino-1-ethoxy-eth-(Z)-ylideneamino]-3-phenyl-propionic acid

2-[2-Benzoylamino-1-ethoxy-eth-(Z)-ylideneamino]-3-phenyl-propionic acid

A

Phenylalanine
150-30-1

Phenylalanine

B

ethyl hippurate
1499-53-2

ethyl hippurate

Conditions
ConditionsYield
With hydrogenchloride In diethyl etherA n/a
B 63%
(±)-N-Boc-2-amino-2-benzylacetonitrile
154279-16-0

(±)-N-Boc-2-amino-2-benzylacetonitrile

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogenchloride In methanol for 6h; Heating;50%
N-(diphenylmethylene)glycine tert-butyl ester
81477-94-3

N-(diphenylmethylene)glycine tert-butyl ester

benzyl bromide
100-39-0

benzyl bromide

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
Stage #1: N-(diphenylmethylene)glycine tert-butyl ester; benzyl bromide With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl In dichloromethane at 20℃; for 1h;
Stage #2: With hydrogenchloride In methanol; water Heating;
50%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With ammonium bicarbonate Ambient temperature; detonation; also with (NH4)2CO3;45%
With ammonium bicarbonate Ambient temperature; detonation; also with (NH4)2CO3;45%
With ammonium hydroxide; Anabaena variabilis phenylalanine ammonia lyase at 30℃; pH=9.5; Kinetics; Enzymatic reaction;
With ammonium hydroxide; phenylalanine ammonia-lyase from Anabaena variabilis N347A mutant In aq. buffer at 35℃; for 12h;
With phenylalanine ammonia lyase from Anabaena variabilis; ammonium carbamate at 30℃; for 22h; pH=9.9; Catalytic behavior; pH-value; Enzymatic reaction;99 %Chromat.
(2R)-N-(diphenylmethylene)[1,2-13 C2, 15 N, 2,2-2 H2 ]glycylbornane-10,2-sultam

(2R)-N-(diphenylmethylene)[1,2-13 C2, 15 N, 2,2-2 H2 ]glycylbornane-10,2-sultam

iodomethylbenzene
620-05-3

iodomethylbenzene

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; lithium hydroxide; n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water45%
2-oxo-3-(phenyl)propionic acid
156-06-9

2-oxo-3-(phenyl)propionic acid

A

Phenylalanine
150-30-1

Phenylalanine

B

Phac-DL-Phe-NH2
83556-31-4

Phac-DL-Phe-NH2

Conditions
ConditionsYield
Stage #1: 2-oxo-3-(phenyl)propionic acid With ammonia; hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis[[bis(3-sulfophenyl)phosphino]methyl]-4,4',7,7'-tetrasulfo-1,1'-binaphthyl octasodium salt In ethanol; water at 60℃; under 31503.2 Torr; for 24h;
Stage #2: With hydrogenchloride In ethanol; water Product distribution / selectivity;
A 15%
B 43%
4-benzyl-2-phenyl-2-oxazolin-5-one
5874-61-3, 21453-79-2, 51127-19-6, 75658-67-2

4-benzyl-2-phenyl-2-oxazolin-5-one

A

Phenylalanine
150-30-1

Phenylalanine

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With potassium In tetrahydrofuran for 4h;A 37%
B 33%
phenyllactic acid
828-01-3

phenyllactic acid

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen at 219.84℃; under 7500.75 Torr; for 2h; Autoclave;30%
With ammonium hydroxide; hydrogen at 180℃; under 7500.75 Torr; for 2h; Autoclave;51.5 %Spectr.
2-Bromo-3-phenyl-propionic acid; compound with ammonia

2-Bromo-3-phenyl-propionic acid; compound with ammonia

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
at 19.9℃; under 37503000 Torr; Product distribution; under shear deformation (360 deg);0.95%
5-benzylidene-2-thiohydantoin
583-46-0

5-benzylidene-2-thiohydantoin

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogenchloride; tin
4-benzyl-oxazolidine-2,5-dione
583-47-1

4-benzyl-oxazolidine-2,5-dione

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogenchloride
5-phenylimidazolidine-2,4-dione
89-24-7

5-phenylimidazolidine-2,4-dione

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With hydrogen iodide
With phosphorus; iodine
With barium dihydroxide; water
diethyl ether
60-29-7

diethyl ether

4-(phenyl-trans-azo)-phenol; compound with phenylalanine

4-(phenyl-trans-azo)-phenol; compound with phenylalanine

A

Phenylalanine
150-30-1

Phenylalanine

B

4-Oxy-azoxybenzol
16054-49-2

4-Oxy-azoxybenzol

2-bromo-3-phenylpropanoic acid
16503-53-0

2-bromo-3-phenylpropanoic acid

Phenylalanine
150-30-1

Phenylalanine

Conditions
ConditionsYield
With ammonia
With ammonia; water
With ammonia; water at 100℃; im Druckrohr;
With ammonia
formic acid
64-18-6

formic acid

Phenylalanine
150-30-1

Phenylalanine

N-formyl-phenylalanine
4289-95-6

N-formyl-phenylalanine

Conditions
ConditionsYield
With acetic anhydride at 20℃; for 1h;100%
With acetic anhydride at 20℃; for 19h;87%
In N,N-dimethyl-formamide for 0.166667h; Heating;81%
Conditions
ConditionsYield
With sodium tetrahydroborate; iodine100%
With zirconium(IV) borohydride In tetrahydrofuran at 25℃; Reduction;90%
With sodium tetrahydroborate; iodine In tetrahydrofuran for 15h; Heating;60%
ethanol
64-17-5

ethanol

Phenylalanine
150-30-1

Phenylalanine

phenylalanine ethyl ester
1795-96-6

phenylalanine ethyl ester

Conditions
ConditionsYield
Stage #1: ethanol; Phenylalanine With thionyl chloride Reflux;
Stage #2: With sodium hydrogencarbonate
100%
With toluene-4-sulfonic acid In toluene at 80℃; for 16h;83%
With hydrogenchloride
methanol
67-56-1

methanol

Phenylalanine
150-30-1

Phenylalanine

methyl 2-amino-3-phenylpropanoate hydrochloride
5619-07-8

methyl 2-amino-3-phenylpropanoate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 5 - 50℃; for 25h;100%
With thionyl chloride at 50℃; for 25h; Cooling with ice;100%
With thionyl chloride at 0 - 20℃; for 20h;99%
Phenylalanine
150-30-1

Phenylalanine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-(tert-butoxycarbonylamino)-3-phenylpropionic acid
4530-18-1

2-(tert-butoxycarbonylamino)-3-phenylpropionic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;100%
With tetramethyl ammoniumhydroxide91%
With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 5h;81%
Phenylalanine
150-30-1

Phenylalanine

bis(2,4-dinitrophenyl) carbonate
7497-12-3

bis(2,4-dinitrophenyl) carbonate

4-benzyl-oxazolidine-2,5-dione
583-47-1

4-benzyl-oxazolidine-2,5-dione

Conditions
ConditionsYield
In tetrahydrofuran at 60℃; for 91h; Product distribution / selectivity;100%
Phenylalanine
150-30-1

Phenylalanine

2-chloro-4-fluorobenzonitrile
60702-69-4

2-chloro-4-fluorobenzonitrile

N-(3-chloro-4-cyanophenyl)phenylalanine
1114547-56-6

N-(3-chloro-4-cyanophenyl)phenylalanine

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 90℃;100%
3-aminopropyltriethoxysilane
919-30-2

3-aminopropyltriethoxysilane

Phenylalanine
150-30-1

Phenylalanine

C18H32N2O4Si

C18H32N2O4Si

Conditions
ConditionsYield
at 160℃; for 0.05h; Product distribution / selectivity; Microwave irradiation (300 W);100%
Phenylalanine
150-30-1

Phenylalanine

benzoyl chloride
98-88-4

benzoyl chloride

DL-N-benzoylphenylalanine
2566-22-5, 2901-76-0, 37002-52-1

DL-N-benzoylphenylalanine

Conditions
ConditionsYield
With sodium hydroxide; N-ethyl-N,N-diisopropylamine In water 1.) 0 deg C, 30 min; 2.) up to RT, 30 min;99%
With sodium hydroxide In water; acetonitrile at 0℃; for 2h;88%
With sodium hydroxide In water for 0.5h;79%
methanol
67-56-1

methanol

Phenylalanine
150-30-1

Phenylalanine

DL-phenylalanine methyl ester
15028-44-1

DL-phenylalanine methyl ester

Conditions
ConditionsYield
With thionyl chloride at -20℃; for 3.66667h; Reflux;99%
With thionyl chloride for 3h; Heating;98%
With sulfuric acid Reflux;92%
Phenylalanine
150-30-1

Phenylalanine

1-benzylisatin
1217-89-6

1-benzylisatin

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
21728-28-9

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester

C35H31N3O4

C35H31N3O4

Conditions
ConditionsYield
In methanol at 30℃; for 4h; Solvent; Time; Concentration; diastereoselective reaction;99%
1-benzyl-5-chloroisatin
26960-68-9

1-benzyl-5-chloroisatin

Phenylalanine
150-30-1

Phenylalanine

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
21728-28-9

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester

C35H30ClN3O4

C35H30ClN3O4

Conditions
ConditionsYield
In methanol at 30℃; for 24h; diastereoselective reaction;99%
Phenylalanine
150-30-1

Phenylalanine

1-benzyl-7-fluoroindoline-2,3-dione
1190109-45-5

1-benzyl-7-fluoroindoline-2,3-dione

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
21728-28-9

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester

C35H30FN3O4

C35H30FN3O4

Conditions
ConditionsYield
In methanol at 30℃; for 24h; diastereoselective reaction;99%
Phenylalanine
150-30-1

Phenylalanine

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

methyl 2-amino-3-phenylpropanoate hydrochloride
5619-07-8

methyl 2-amino-3-phenylpropanoate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 18h;99%
formaldehyd
50-00-0

formaldehyd

Phenylalanine
150-30-1

Phenylalanine

(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
67123-97-1

(R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water for 4.5h; Heating / reflux;98.9%
With hydrogenchloride69%
With hydrogenchloride In water for 6h; Reflux;33%
phthalic anhydride
85-44-9

phthalic anhydride

Phenylalanine
150-30-1

Phenylalanine

N-phthaloylphenylalanine
3588-64-5

N-phthaloylphenylalanine

Conditions
ConditionsYield
at 170℃; for 2h;98%
In acetonitrile at 145℃; Sealed tube;96%
at 170℃; for 2.5h;93%
maleic anhydride
108-31-6

maleic anhydride

Phenylalanine
150-30-1

Phenylalanine

N-maleyl-D,L-phenylalanine
96661-85-7

N-maleyl-D,L-phenylalanine

Conditions
ConditionsYield
In acetic acid at 20℃;98%
In acetic acid for 0.166667h; Heating;81%
Phenylalanine
150-30-1

Phenylalanine

Bz-Gly-ONPh
3101-11-9

Bz-Gly-ONPh

N-hippuroyl-3-phenyl-alanine
4703-39-3

N-hippuroyl-3-phenyl-alanine

Conditions
ConditionsYield
With sodium hydroxide In water; butan-1-ol Ambient temperature;98%
m-carborane-1,7-dicarboxylic acid dichloride
23810-52-8

m-carborane-1,7-dicarboxylic acid dichloride

Phenylalanine
150-30-1

Phenylalanine

C2B10H10(CONHCH(CH2C6H5)COOH)2
186822-50-4

C2B10H10(CONHCH(CH2C6H5)COOH)2

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water byproducts: NaCl; stirring (20-30°C, 2-3 h), aq. HCl addn.; washing (water), drying (vac.); elem. anal.;98%
(S)-benzyl 4-(1-benzo[d][1m2m3]triazol-1-yl)-3-(benzyloxycarbonylamino)-4-oxobutanoate
1052265-49-2

(S)-benzyl 4-(1-benzo[d][1m2m3]triazol-1-yl)-3-(benzyloxycarbonylamino)-4-oxobutanoate

Phenylalanine
150-30-1

Phenylalanine

2-((S)-4-(benzyloxy)-2-(benzyloxycarbonylamino)-4-oxobutanamido)-3-phenylpropanoic acid
1052265-93-6

2-((S)-4-(benzyloxy)-2-(benzyloxycarbonylamino)-4-oxobutanamido)-3-phenylpropanoic acid

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 2h;98%
formaldehyd
50-00-0

formaldehyd

Phenylalanine
150-30-1

Phenylalanine

1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ; hydrochloride
41994-51-8

1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 4.5h; Reflux;98%
Phenylalanine
150-30-1

Phenylalanine

((S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide)
1644308-41-7

((S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide)

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

C34H30Cl3N3NiO3

C34H30Cl3N3NiO3

Conditions
ConditionsYield
With potassium carbonate In methanol at 60℃; for 3h; Temperature; diastereoselective reaction;98%
Phenylalanine
150-30-1

Phenylalanine

(S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidine-2-carboxamide

(S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidine-2-carboxamide

nickel(II)-(S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidine-2-carboxamide/(S)-phenylalanine Schiff base complex

nickel(II)-(S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidine-2-carboxamide/(S)-phenylalanine Schiff base complex

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 72h;98%
With potassium carbonate In methanol at 60℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; diastereoselective reaction;98%
Phenylalanine
150-30-1

Phenylalanine

N-benzyl-5-fluoroisatin
366799-82-8

N-benzyl-5-fluoroisatin

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester
21728-28-9

(2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid ethyl ester

C35H30FN3O4

C35H30FN3O4

Conditions
ConditionsYield
In methanol at 30℃; for 24h; diastereoselective reaction;98%
benzoic acid N-hydroxysuccinimide ester
23405-15-4

benzoic acid N-hydroxysuccinimide ester

Phenylalanine
150-30-1

Phenylalanine

DL-N-benzoylphenylalanine
2566-22-5, 2901-76-0, 37002-52-1

DL-N-benzoylphenylalanine

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water at 20℃; for 2h;97%
Phenylalanine
150-30-1

Phenylalanine

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

C21H18ClNO4
1033595-55-9

C21H18ClNO4

Conditions
ConditionsYield
With [bmIm]OH In water Heating;97%
Phenylalanine
150-30-1

Phenylalanine

indole-2,3-dione
91-56-5

indole-2,3-dione

(3E)-3-benzylidene-1,3-dihydro-2H-indol-2-one
23782-37-8

(3E)-3-benzylidene-1,3-dihydro-2H-indol-2-one

C31H25N3O2

C31H25N3O2

Conditions
ConditionsYield
In methanol at 60℃; for 3h; diastereoselective reaction;97%
1-dodecyl alcohol
112-53-8

1-dodecyl alcohol

Phenylalanine
150-30-1

Phenylalanine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

racemic 1-(dodecyloxy)-1-oxo-3-phenylpropan-2-aminium 4-methyl benzenesulfonate

racemic 1-(dodecyloxy)-1-oxo-3-phenylpropan-2-aminium 4-methyl benzenesulfonate

Conditions
ConditionsYield
In toluene Reflux;97%
Stage #1: 1-dodecyl alcohol; Phenylalanine In neat (no solvent) at 120℃; for 0.0833333h; Green chemistry;
Stage #2: toluene-4-sulfonic acid In neat (no solvent) at 130 - 135℃; Green chemistry;
82%
N-benzyloxycarbonyl-3-aminopropionic acid succinimide ester
53733-97-4

N-benzyloxycarbonyl-3-aminopropionic acid succinimide ester

Phenylalanine
150-30-1

Phenylalanine

(±)-Cbz-βAla-Phe-OH
21612-32-8

(±)-Cbz-βAla-Phe-OH

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water; acetone at 20℃; for 5h;97%

150-30-1Relevant articles and documents

Systematic pH Study on the Acid- and Base-Catalyzed Racemization of Free Amino Acids To Determine the Six Constants, One for Each of the Three Ionic Species

Baum, Rocky,Smith, Grant Gill

, p. 7325 - 7327 (1986)

Computer analysis of pH profiles for racemization of four amino acids at 142 deg C led to the determination of the six absolute rate constants, one for each ionic species of amino acid in aqueoussolution catalyzed by hydronium and hydroxide ions.A comparison is made to show the effect of using all six constants to express the observed rate constants, as opposed to using only four in previous studies.The analyses also allowed the calculation of amino acid pKa values at elevated temperatures.

Stress degradation study of bortezomib: Effect of co-solvent, isolation and characterization of degradation products by UHPLC-Q-TOF-MS/MS and NMR and evaluation of the toxicity of the degradation products

Udutha, Suresh,Borkar, Roshan M.,Shankar,Sony,Jala, Aishwarya,Vamshi Krisna,Kiran Kumar,Misra,Prabhakar,Srinivas

, p. 8178 - 8191 (2021)

Bortezomib (BTZ) is a first-in-class, potent reversible inhibitor of proteasome used in the treatment of multiple myeloma, the second most common hematological cancer. Stress degradation studies were performed to investigate the inherent stability of the drug according to ICH recommended guidelines Q1A (R2). Stress experiments were carried out in two ways using acetonitrile and methanol as co-solvents under various conditions. A selective stability-indicating LC-MS method has been developed to separate all degradation products of the drug on a Hibar-Purospher STAR, C18 (250 × 4.6 mm, 5 μm) column using a mobile phase consisting of 0.1% formic acid and acetonitrile in the gradient mode. BTZ was found to undergo degradation under acidic, basic, neutral hydrolysis and oxidative conditions, whereas it was stable under other conditions. Thirteen degradation products (DP-1-DP-13) were identified using acetonitrile as a co-solvent. Additionally, three (DP-14-DP-16) degradation products were found where methanol was used as a co-solvent. A total of 16 (DP-1-DP-16) degradation products were characterized by liquid chromatography-tandem mass spectrometry (LC-ESI-Q-TOF/MS/MS) and high-resolution mass spectrometry (HRMS). Major degradation products, DP-3, DP-6, DP-9, DP-10, DP-11 and DP-12, formed under oxidation conditions were isolated using preparative HPLC and characterized by 1D and 2D NMR experiments. Furthermore, in vitro cytotoxicity of isolated DPs was tested on normal cell lines such as CHO-K1, HEK-293 and NRK-49F by MTT assays. This study revealed that they were around 2-6 times less toxic as compared with the standard control of the drug and DP-10 showed relatively more toxicity than other isolated DPs against rat kidney cells at 18.20 μM. In silico toxicity studies suggested that BTZ and its DPs can be hepatotoxic and genotoxic resulting in severe toxicity.

Catalytic amino acid production from biomass-derived intermediates

Deng, Weiping,Wang, Yunzhu,Zhang, Sui,Gupta, Krishna M.,Hülsey, Max J.,Asakura, Hiroyuki,Liu, Lingmei,Han, Yu,Karp, Eric M.,Beckham, Gregg T.,Dyson, Paul J.,Jiang, Jianwen,Tanaka, Tsunehiro,Wang, Ye,Yan, Ning

, p. 5093 - 5098 (2018)

Amino acids are the building blocks for protein biosynthesis and find use in myriad industrial applications including in food for humans, in animal feed, and as precursors for bio-based plastics, among others. However, the development of efficient chemical methods to convert abundant and renewable feedstocks into amino acids has been largely unsuccessful to date. To that end, here we report a heterogeneous catalyst that directly transforms lignocellulosic biomass-derived α-hydroxyl acids into α-amino acids, including alanine, leucine, valine, aspartic acid, and phenylalanine in high yields. The reaction follows a dehydrogenation-reductive amination pathway, with dehydrogenation as the rate-determining step. Ruthenium nanoparticles supported on carbon nanotubes (Ru/CNT) exhibit exceptional efficiency compared with catalysts based on other metals, due to the unique, reversible enhancement effect of NH3 on Ru in dehydrogenation. Based on the catalytic system, a two-step chemical process was designed to convert glucose into alanine in 43% yield, comparable with the well-established microbial cultivation process, and therefore, the present strategy enables a route for the production of amino acids from renewable feedstocks. Moreover, a conceptual process design employing membrane distillation to facilitate product purification is proposed and validated. Overall, this study offers a rapid and potentially more efficient chemical method to produce amino acids from woody biomass components.

New diketopiperazine derivatives from a deep-sea-derived Nocardiopsis alba SCSIO 03039

Zhang, Qingbo,Li, Sumei,Chen, Yuchan,Tian, Xinpeng,Zhang, Haibo,Zhang, Guangtao,Zhu, Yiguang,Zhang, Si,Zhang, Weimin,Zhang, Changsheng

, p. 31 - 36 (2013)

The strain SCSIO 03039 was isolated from a sediment sample in the Indian Ocean and was characterized as a Nocardiopsis alba species on the basis of its 16S rRNA gene sequence. Seven diketopiperazines (DKPs), including two new DKPs nocazines D (2a) and E (2b), and five known DKPs (1, 3-6), were isolated from N. alba SCSIO 03039, along with two known compounds 2-methoxy-1,4-naphthoquinone (7) and 1-hydroxy-4-methoxy-2-naphthoic acid (8). Their structures were elucidated by mass and NMR spectroscopic analyses. The structure of methoxyneihumicin (1), previously proposed in a conference poster lacking publicly available experimental data, was validated for the first time by detailed NMR analyses and X-ray diffraction study. The two enantiomers nocazines D (2a) and E (2b) were isolated as a mixture. Compounds 3 and 4 were only known as synthetic compounds before. Methoxyneihumicin (1) exhibited in vitro cytotoxicities against MCF-7 and SF-268 with IC 50 values of 4.6 and 12.7 μM, respectively, better than those of 6 (22.0 and 20.6 μM). The other compounds showed less pronounced cytotoxities against three tested human cancer cell lines and no compounds displayed antibacterial activities toward four indicator strains.

Primordial reductive amination revisited

Huber, Claudia,W?chtersh?user, Günter

, p. 1695 - 1697 (2003)

Amino acids are formed efficiently by reductive amination of α-keto acids under aqueous, conditions with freshly precipitated FeS or Fe(OH)2 and with NH3, CH3NH2 or (CH3)2NH at pH values near their pKa.

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Albertson,Tullar

, p. 502 (1945)

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Albertson,Archer

, p. 308 (1945)

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Collman,Buckingham

, p. 3039 (1963)

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Nummularine-O, a cyclopeptide alkaloid from Zizyphus nummularia

Pandey,Dwivedi,Shah,Eckhardt

, p. 2690 - 2691 (1986)

In addition to the known peptide alkaloid jubanine-B, a new peptide alkaloid, nummularine-O, has been isolated from the stem bark of Zizyphus nummularia and their structures have been elucidated by chemical and spectroscopic methods.

Primordial Amino Acids by Reductive Amination of α-Oxo Acids in Conjunction with the Oxidative Formation of Pyrite

Hafenbradi, D.,Keller, M.,Waechtershaeuser, G.,Stetter, K. O.

, p. 5179 - 5182 (1995)

The theory of an autotrophic origin of life postulates a primordial formation of amino acids by a mild and specific chemical energy source, namely by the reductive amination of α-oxo acids in conjunction with the oxidative formation of pyrite.Here we show experimental proof for this reaction, which involves carbon dioxide as catalyst.

Artificial Transaminase Carriyng a Synthetic Macrocyclic Binding Group

Winkler, Jeffrey,Coutouli-Argyropoulou, Evdoxia,Leppkes, Reinhard,Breslow, Ronald

, p. 7198 - 7199 (1983)

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Khan,Kidwai

, p. 822 (1973)

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Autorecycling System for the Synthesis of α-Amino-acids by the Reductive Amination of α-Keto-acids catalysed by 1,5-Dihydro-5-deazaflavin

Yoneda, Fumio,Kuroda, Kazunori

, p. 927 - 929 (1982)

An effective autorecycling system for the biomimetic synthesis of α-amino-acids by the reductive amination of α-keto-acids has been achieved for the first time using 10-aryl-5-deazaflavin, ammonium formate, and formic acid; each mole of the 5-deazaflavin catalyses the reduction, by formic acid, of up to 20 moles of the α-imino-acids formed in situ from the α-keto-acids and ammonium formate.

KINETIC STUDY OF A Zn2 + -CATALYZED TRANSAMINATION REACTION BETWEEN PYRIDOXAMINE ANALOGS WITH A PYRIDINOPHANE STRUCTURE AND alpha -KETO ACIDS.

Tachibana,Ando,Kuzuhara

, p. 2263 - 2266 (1983)

The kinetics of the nonenzymatic transamination reaction from pyridoxamine analogs with a pyridinophane structure to a-keto acids catalyzed by Zn**2** plus were investigated by monitoring the changes in the absorption spectra in methanol. It was found that these reactions obeyed first-order kinetics for the formation of the Zn**2** plus chelate of an aldimine. No appreciable change in the reaction rate was observed when the concentration of the a-keto acid was increased, indicating that the isomerization of the ketimine chelate to the aldimine chelate is the rate-determining step. There was a considerable enhancement of the reaction rate when the molar ratio of the zinc ion to the pyridoxamine analogs was reduced from 1/1 to 0. 5/1.

Method for the Racemization of Optically Active Amino Acids

Yamada, Shigeki,Hongo, Chikara,Yoshioka, Ryuzo,Chibata, Ichiro

, p. 843 - 846 (1983)

A practical method for the racemization of optically active amino acids has been developed.A wide variety of optically active α-amino acids, including neutral amino acids, acidic amino acids, basic amino acids, and imino acids, could be racemized by heating in a medium of acetic acid at 80-100 deg C for 1 h in the presence of 0.05 molar equiv of an aliphatic or an aromatic aldehyde.The factors influencing the racemization were investigated.Phenylglycine, (p-hydroxyphenyl)glycine, and serine could be racemized without complete dissolution of the optically active isomers.Thus, isolation of the racemic modification was easily achieved by simple filtration of the racemic modification suspended in the reaction mixture.The mechanism of the racemization is discussed.

Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions

Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.

, (2020/07/15)

The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko

, p. 11047 - 11059 (2020/10/12)

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

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