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Chemical Structure| 2835-06-5 Chemical Structure| 2835-06-5
Chemical Structure| 2835-06-5

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H-DL-Phg-OH is a DL-phenylglycine derivative with significance in enzyme inhibitor and ligand design.

Synonyms: DL-α-Phenylglycine; 2-Phenylglycine

4.5 *For Research Use Only !

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Huddleston, Morgan ;

Abstract: Electrocatalytic valorization of biomass-derived intermediate compounds to value-added products has emerged as a promising approach to mitigate carbon emissions. Capitalizing on renewable electricity as a green energy input for conducting paired electrocatalysis is a promising approach in the field of biorefining. Simultaneous oxidation and reduction of 5-hydroxymethylfurfural (HMF) yields high value products such as 2,5-formylfurancarboxylic acid (FFCA) and 2,5-bishydroxymethylfurfural (BHMF) with applications in the food industry, fuel additives, and pharmaceuticals. Simultaneous upgrading of biomass derived 5-hydroxymethylfurfural (HMF) at both the anode and cathode has been previously explored, however the challenge of tunable selectivity has not been overcome. Traditional electrochemical methods often suffer from energy inefficiencies due to the need for a second conversion at the counter electrode, which can produce non-value-added byproducts. Amino acids are a key example of highly valuable products derived from biomass oxidation followed by reductive amination. Pharmaceutical and food industries will benefit from an alternative strategy to produce amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. HMF can be proven to selectively yield 5-formyl-2-furancarboxylic acid (FFCA) under the same electrochemical conditions as HMF hydrogenation to 2,5-bishydroxymethylfuran (BHMF). With 4-acetamido TEMPO (ACT) as a homogeneous oxidation mediator and silver galvanically displaced copper foam (Ag/Cu) as the cathodic electrocatalyst, both electrochemical conversions can be observed in an H-type cell simultaneously. By employing pH 10 carbonate buffer as the optimized electrolyte, water proves to be an effective proton source for both conversion which demonstrates the extremely mild conditions. HMF anodic conversion of 94% leads to FFCA formation of 83% yield and simultaneous HMF cathodic conversion of 100% yields BHMF at 99%. HMF also oxidizes to 2,5-diformylfuran (DFF) with 75% yield and subsequent amination with ammonium hydroxide followed by reductive hydrogenation yields 2,5-(dimethylamino) furan (DMAF). This paired electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination yield amino acids as the final products. Glycine, Alanine, and Leucine were synthesized with N-hydroxyphthalimide (NHPI) as the oxidation mediator and NH3 as the nitrogen source to yields of 70, 80, and 90%. Phenylalanine required tetramethylpiperidine Noxyl (TEMPO) oxidation mediator with applying the same 2.7 V yielded 100%. Our paired electrolysis improves selectivity and doubles electron efficiency, with the flow electrolyzer demonstrating its potential for large-scale applications. The main challenge for widespread use of our proposed paired electrocatalytic method is the cost of industrial-scale small molecule production. Paired electrocatalysis offers an alternative by using both half-reactions in an electrochemical cell to produce value-added chemicals from biomass feedstocks. The operational principles and benefits of various cell configurations are compared, along with an analysis of electrocatalysts. Heterogeneous and bifunctional catalysts in paired electrocatalysis optimize energy and chemical use, eliminating the need for purification. The future will require further optimization to enhance the benefits of biomass valorization through paired electrocatalysis, while addressing challenges like cost of precursors, large-scale facility expenses, and widespread adoption of sustainably sourced energy.

Purchased from AmBeed: ; ; ; ; ; ; ;

Kaili Yan ; Morgan L. Huddleston ; Brett A. Gerdes ; Yujie Sun ;

Abstract: Electrochemical conversion of biomass-derived intermediate compounds to high-value products has emerged as a promising approach in the field of biorefinery. Biomass upgrading allows for the production of chemicals from non-fossil-based carbon sources and capitalization on electricity as a green energy input. Amino acids, as products of biomass upgrading, have received relatively little attention. Pharmaceutical and food industries will benefit from an alternative strategy for the production of amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. Herein, we report an electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination to yield amino acids as the final products. Such a strategy takes advantage of both reactions at the anode and cathode and produces amino acids under ambient conditions with high energy efficiency. A flow electrolyzer was also successfully employed for the conversion of α-hydroxyl acids to amino acids, highlighting its great potential for large-scale application.

Purchased from AmBeed: ; ; ; ; 56-40-6 ; 156-06-9 ; ; ; ; ; ; ; 828-01-3 ;

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Product Details of H-DL-Phg-OH

CAS No. :2835-06-5
Formula : C8H9NO2
M.W : 151.16
SMILES Code : O=C(O)C(N)C1=CC=CC=C1
Synonyms :
DL-α-Phenylglycine; 2-Phenylglycine
MDL No. :MFCD00064402

Safety of H-DL-Phg-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of H-DL-Phg-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2835-06-5 ]

[ 2835-06-5 ] Synthesis Path-Downstream   1~9

  • 2
  • [ 108-24-7 ]
  • [ 2835-06-5 ]
  • [ 14257-84-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In water; N,N-dimethyl-formamide; at 20℃; General procedure: To a solution of amino acid (50 mmol) in a 50 mL solution (25 mL DMF and 25 mL H2O), 52 mmol of acetic anhydride and triethylamine (60 mmol, 6.06 g) were added. The solution was stirred at room temperature overnight. After reaction, the solution was evacuated at reduced pressure to remove DMF. The residue was added to 30 mL of H2O, stirred at rt for 40 min, after which the pH value of the solution was changed to 7.0 with a solution of sodium carbonate and extracted with 20 mL of ethyl acetate three times. The combined organic solution was washed with saturated brine and then dried over anhydrous magnesium sulfate. The organic solution was evacuated to remove the organic solvent, and the residue was chromatographed to afford pure amino acid amides.
  • 3
  • NaOH-dissolved [ No CAS ]
  • [ 2835-06-5 ]
  • [ 14257-84-2 ]
YieldReaction ConditionsOperation in experiment
553 g (87%) With sodium hydroxide; acetic anhydride; In water-are; water; (a) D-alpha-Acetamido-alpha-phenylacetic acid (2a) 500 g (3.31 mol) of D-alpha-amino-alpha-phenylacetic acid are suspended in 6 liters of water, and the suspension is cooled to 10 C. and 132 g (3.31 mol) of NaOH dissolved in 1,000 ml of water are added. After 15 minutes, 675 g (6.62 mol) of acetic anhydride and then 397 g (9.93 mol) of NaOH--dissolved in 1,000 ml of water--are poured into the clear solution at 0 C., stirring rapidly. The temperature increases from 0 C. to 30 C. during this. The solution is stirred for a further 20 minutes at pH 9 to 10 in an ice/sodium chloride bath and is then acidified to pH 1 with concentrated hydrochloric acid (about 1 liter). The suspension is then stirred for 10 minutes, cooled to 10 C., filtered with suction and washed with 10 liters of water. The product is dried over KOH in vacuo. Yield: 553 g (87%). C10 H11 NO3 (193.2). Melting point 190-191 C. [alpha]58920 =-218.6 (C=1, C2 H5 OH).
  • 4
  • [ 75-36-5 ]
  • [ 2835-06-5 ]
  • [ 14257-84-2 ]
  • 5
  • [ 103854-64-4 ]
  • [ 2835-06-5 ]
  • [ 1415735-19-1 ]
  • 6
  • [ 612-28-2 ]
  • [ 2835-06-5 ]
  • [ 2622-63-1 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate; In toluene; at 140℃; for 24h;Schlenk technique; Sealed tube; In a clean dry 10 ml Schlenk reaction tube, sequentially adding a 2-nitro-N-methylaniline 38 mg, benzene glycine 113 mg, potassium carbonate 80 mg, in order to 1 ml of toluene as a solvent, the reaction tube seal, in 140 °C reaction under 24 hours. After the reaction, the reaction mixture directly by rotating the evaporimeter turns on lathe does, then the volume ratio of 8:1 of petroleum ether and ethyl acetate as the eluant, by separating by silica gel column, to obtain 39 mg light yellow solid, yield 79percent.
  • 7
  • [ 69976-70-1 ]
  • [ 2835-06-5 ]
  • [ 68674-69-1 ]
YieldReaction ConditionsOperation in experiment
90% With palladium; In water; at 130℃; for 20h;Inert atmosphere; Schlenk technique; In a clean dry 10 ml Schlenk reaction tube, the mass fraction of sequentially adding 10% Pd/C4 . 5 mg, 5-methyl-2-nitro-acetophenone 45 mg, benzene glycine 113 mg, 1 ml of water as a solvent, is condensed on the return is, under the protection of nitrogen 130 o C reaction 20 hours. After the reaction, through the filter, the catalyst can be directly used in the next cycle, the filtrate after direct turns on lathe does a small amount of petroleum ether and ethyl acetate (volume ratio is 40:1) dissolving, through a short silica gel column of column separation, to obtain 54 mg white solid, yield 90%.
  • 8
  • [ 456-88-2 ]
  • [ 2835-06-5 ]
  • 3,5-bis(3-fluorophenyl)-2-phenylpyridine [ No CAS ]
  • 9
  • [ 652-12-0 ]
  • [ 2835-06-5 ]
  • 2-phenyl-2-(4,5,6,7-tetrafluoro-1,3-dioxoisoindolin-2-yl)acetic acid [ No CAS ]
 

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