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Cas Database

63-91-2

63-91-2

Identification

  • Product Name:L-Phenylalanine

  • CAS Number: 63-91-2

  • EINECS:200-568-1

  • Molecular Weight:165.192

  • Molecular Formula: C9H11NO2

  • HS Code:2922.49

  • Mol File:63-91-2.mol

Synonyms:beta-Phenylalnine, (-)-;Alanine, phenyl-;(-)-.beta.-Phenylalanine;(2S)-2-azaniumyl-3-phenyl-propanoate;(S)-Phenylalanine;alpha-Amino-beta-phenylpropionic acid, L-;(S)-alpha-Aminohydrocinnamic acid;beta-phenylalanine;L-.beta.-Phenylalanine;(2S)-2-amino-3-phenyl-propanoic acid;Phenylalamine;L-Antibiotic FN 1636;2-Amino-3-phenylpropionic acid, L-;Phenylalanine (USP);Hydrocinnamic acid, alpha-amino-;(L)-Phenylalanine;Alanine, phenyl-, L-;L-Phenylalanine (JP14);

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

  • Fire-fighting measures: Suitable extinguishing media Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. Flash point data for this chemical are not available; however, it is probably combustible. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:L-Phenylalanine
  • Packaging:50g
  • Price:$ 403
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  • Manufacture/Brand:Usbiological
  • Product Description:L-Phenylalanine
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  • Product Description:L-Phenylalanine >98.0%(HPLC)(T)
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  • Product Description:L-Phenylalanine >98.0%(HPLC)(T)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:L-Phenylalanine 99%, FCC
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:L-Phenylalanine 99%, natural, FCC, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:L-Phenylalanine 99%, FCC
  • Packaging:5kg-k
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:L-Phenylalanine 99%, natural, FCC, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:L-Phenylalanine United States Pharmacopeia (USP) Reference Standard
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Relevant articles and documentsAll total 445 Articles be found

Enhanced carboxypeptidase efficacies and differentiation of peptide epimers

Sung, Yu-Sheng,Putman, Joshua,Du, Siqi,Armstrong, Daniel W.

, (2022/01/29)

Carboxypeptidases enzymatically cleave the peptide bond of C-terminal amino acids. In humans, it is involved in enzymatic synthesis and maturation of proteins and peptides. Carboxypeptidases A and Y have difficulty hydrolyzing the peptide bond of dipeptides and some other amino acid sequences. Early investigations into different N-blocking groups concluded that larger moieties increased substrate susceptibility to peptide bond hydrolysis with carboxypeptidases. This study conclusively demonstrates that 6-aminoquinoline-N-hydroxysuccimidyl carbamate (AQC) as an N-blocking group greatly enhances substrate hydrolysis with carboxypeptidase. AQC addition to the N-terminus of amino acids and peptides also improves chromatographic peak shapes and sensitivities via mass spectrometry detection. These enzymes have been used for amino acid sequence determination prior to the advent of modern proteomics. However, most modern proteomic methods assume that all peptides are comprised of L-amino acids and therefore cannot distinguish L-from D-amino acids within the peptide sequence. The majority of existing methods that allow for chiral differentiation either require synthetic standards or incur racemization in the process. This study highlights the resistance of D-amino acids within peptides to enzymatic hydrolysis by Carboxypeptidase Y. This stereoselectivity may be advantageous when screening for low abundance peptide stereoisomers.

Recreating the natural evolutionary trend in key microdomains provides an effective strategy for engineering of a thermomicrobial N-demethylase

Gu, Zhenghua,Guo, Zitao,Shao, Jun,Shen, Chen,Shi, Yi,Tang, Mengwei,Xin, Yu,Zhang, Liang

, (2022/03/09)

N-demethylases have been reported to remove the methyl groups on primary or secondary amines, which could further affect the properties and functions of biomacromolecules or chemical compounds; however, the substrate scope and the robustness of N-demethylases have not been systematically investigated. Here we report the recreation of natural evolution in key microdomains of the Thermomicrobium roseum sarcosine oxidase (TrSOX), an N-demethylase with marked stability (melting temperature over 100 C) and enantioselectivity, for enhanced substrate scope and catalytic efficiency on -C-N-bonds. We obtained the structure of TrSOX by crystallization and X-ray diffraction (XRD) for the initial framework. The natural evolution in the nonconserved residues of key microdomains—including the catalytic loop, coenzyme pocket, substrate pocket, and entrance site—was then identified using ancestral sequence reconstruction (ASR), and the substitutions that accrued during natural evolution were recreated by site-directed mutagenesis. The single and double substitution variants catalyzed the N-demethylation of N-methyl-L-amino acids up to 1800- and 6000-fold faster than the wild type, respectively. Additionally, these single substitution variants catalyzed the terminal N-demethylation of non-amino-acid compounds and the oxidation of the main chain -C-N- bond to a -C=N- bond in the nitrogen-containing heterocycle. Notably, these variants retained the enantioselectivity and stability of the initial framework. We conclude that the variants of TrSOX are of great potential use in N-methyl enantiomer resolution, main-chain Schiff base synthesis, and alkaloid modification or degradation.

Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets

Li, Tingting,Xu, Bo

supporting information, p. 2673 - 2678 (2021/08/03)

Main observation and conclusion: We describe a practical and general protocol for immobilization of heterogeneous catalysts to mechanically robust porous ultra-high molecular weight polyethylene tablets using inter-facial Lifshitz-van der Waals Interactions. Diverse types of powderous catalysts, including Cu, Pd/C, Pd/Al2O3, Pt/C, and Rh/C have been immobilized successfully. The immobilized catalysts are mechanistically robust towards stirring in solutions, and they worked well in diverse synthetic reactions. The immobilized catalyst tablets are easy to handle and reused. Moreover, the metal leaching of immobilized catalysts was reduced significantly.

Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity

De Cesare, Silvia,McKenna, Catherine A.,Mulholland, Nicholas,Murray, Lorna,Bella, Juraj,Campopiano, Dominic J.

supporting information, p. 4904 - 4909 (2021/06/16)

Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that thel-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range ofN-acyl-amino acid substrates. This activity was revealed by1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used to probe the subtle structural selectivity of the biocatalyst using a substrate that could adopt different rotameric conformations.

A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids

Varga, Andrea,Csuka, Pál,Sonesouphap, Orlavanah,Bánóczi, Gergely,To?a, Monica Ioana,Katona, Gabriel,Molnár, Zsófia,Bencze, László Csaba,Poppe, László,Paizs, Csaba

, p. 185 - 194 (2020/04/28)

A novel phenylalanine ammonia-lyase of the psychrophilic yeast Pseudozyma antarctica (PzaPAL) was identified by screening microbial genomes against known PAL sequences. PzaPAL has a significantly different substrate binding pocket with an extended loop (26 aa long) connected to the aromatic ring binding region of the active site as compared to the known PALs from eukaryotes. The general properties of recombinant PzaPAL expressed in E. coli were characterized including kinetic features of this novel PAL with L-phenylalanine (S)-1a and further racemic substituted phenylalanines rac-1b-g,k. In most cases, PzaPAL revealed significantly higher turnover numbers than the PAL from Petroselinum crispum (PcPAL). Finally, the biocatalytic performance of PzaPAL and PcPAL was compared in the kinetic resolutions of racemic phenylalanine derivatives (rac-1a-s) by enzymatic ammonia elimination and also in the enantiotope selective ammonia addition reactions to cinnamic acid derivatives (2a-s). The enantiotope selectivity of PzaPAL with o-, m-, p-fluoro-, o-, p-chloro- and o-, m-bromo-substituted cinnamic acids proved to be higher than that of PcPAL.

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
With phosphate buffer; chymotrypsine; at 25 ℃; Product distribution; Rate constant; hydrolysis, various substrates under different reaction conditions;
Conditions
Conditions Yield
With Z-Phe-His-Leu; Tris-KCl buffer; water; cetyltrimethylammonim bromide; N,N-dimethyl-N-tetradecyltetradecan-1-aminium bromide; In acetonitrile; at 25 ℃; Rate constant; variation of ionic strength; enantioselectivity (L/D);
Conditions
Conditions Yield
With cell extract of Sphingomonas paucimobilis SC 16113; In water; at 42 ℃; for 20h; Enzymatic reaction;
48 % Chromat.
49.5 % Chromat.
angiotensin II
4474-91-3

angiotensin II

angiotensin II-(1-7)
51833-78-4

angiotensin II-(1-7)

Conditions
Conditions Yield
With wheat carboxypeptidase from wheat bran; at 30 ℃; Rate constant; pH 4.0; structure-reactivity relationship;
carriebowmide

carriebowmide

(R)-2-Hydroxy-3-methylbutyric acid
17407-56-6

(R)-2-Hydroxy-3-methylbutyric acid

N-methyl-L-leucine
3060-46-6

N-methyl-L-leucine

N-methyl-D-phenylalanine
56564-52-4

N-methyl-D-phenylalanine

Conditions
Conditions Yield
With hydrogenchloride; water; at 115 ℃; for 18h;
carriebowmide sulfone
1187486-26-5

carriebowmide sulfone

N-methyl-L-leucine
3060-46-6

N-methyl-L-leucine

L-methionine sulfone
7314-32-1,1118-85-0

L-methionine sulfone

N-methyl-D-phenylalanine
56564-52-4

N-methyl-D-phenylalanine

(2S,3R)-3-amino-2-methylhexanoic acid

(2S,3R)-3-amino-2-methylhexanoic acid

Conditions
Conditions Yield
With hydrogenchloride; water; at 110 ℃; for 18.5h;
trichodepsipeptide A
1342309-23-2

trichodepsipeptide A

(R)-2-Hydroxy-3-methylbutyric acid
17407-56-6

(R)-2-Hydroxy-3-methylbutyric acid

(S)-2-Hydroxy-3-methylbutanoic acid
17407-55-5

(S)-2-Hydroxy-3-methylbutanoic acid

(R)-2-hydroxy-4-methylpentanoic acid
20312-37-2,498-36-2

(R)-2-hydroxy-4-methylpentanoic acid

(S)-2-hydroxyl-3,3-dimethylbutyric acid
13748-90-8,498-36-2

(S)-2-hydroxyl-3,3-dimethylbutyric acid

N-methyl-L-leucine
3060-46-6

N-methyl-L-leucine

N-methyl-D-leucine
31321-74-1

N-methyl-D-leucine

Conditions
Conditions Yield
With hydrogenchloride; water; at 100 ℃; for 24h; Sealed tube;
trichodepsipeptide B
1342309-24-3

trichodepsipeptide B

(R)-2-Hydroxy-3-methylbutyric acid
17407-56-6

(R)-2-Hydroxy-3-methylbutyric acid

(S)-2-Hydroxy-3-methylbutanoic acid
17407-55-5

(S)-2-Hydroxy-3-methylbutanoic acid

(R)-2-hydroxy-4-methylpentanoic acid
20312-37-2,498-36-2

(R)-2-hydroxy-4-methylpentanoic acid

(S)-2-hydroxyl-3,3-dimethylbutyric acid
13748-90-8,498-36-2

(S)-2-hydroxyl-3,3-dimethylbutyric acid

N-methyl-L-leucine
3060-46-6

N-methyl-L-leucine

N-methyl-D-leucine
31321-74-1

N-methyl-D-leucine

Conditions
Conditions Yield
With hydrogenchloride; water; at 100 ℃; for 24h; Sealed tube;
2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-L-phenylalanyl)-β-D-glucopyranose
75719-92-5

2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-L-phenylalanyl)-β-D-glucopyranose

β-D-glucose
492-61-5

β-D-glucose

glycylglycine
556-50-3

glycylglycine

Conditions
Conditions Yield
With hydrogen; carboxypeptidase A; palladium on activated charcoal; 1.) acetic acid-2-methoxyethanol; 2.) water, 25 deg C, 12 h;
2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-L,D-phenylalanyl)-α-D-glucopyranose
75719-90-3,75719-91-4,75719-92-5,75719-93-6

2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycyl-L,D-phenylalanyl)-α-D-glucopyranose

β-D-glucose
492-61-5

β-D-glucose

glycylglycine
556-50-3

glycylglycine

glycylglycyl-D-phenylalanine
824945-27-9

glycylglycyl-D-phenylalanine

Conditions
Conditions Yield
With hydrogen; carboxypeptidase A; palladium on activated charcoal; 1.) acetic acid-2-methoxyethanol; 2.) water, 25 deg C;

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