27172-85-6

Usage

Uses

Used in Pharmaceutical Synthesis:
3-phenyl-DL-alanine hydrochloride is used as a chiral building block for the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the creation of complex molecules with specific biological activities, contributing to the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-phenyl-DL-alanine hydrochloride is utilized as a precursor in the production of drugs and biologically active molecules. Its presence in the synthesis process can influence the pharmacological properties of the final product, enhancing their efficacy and selectivity.
Used in Research and Development:
3-phenyl-DL-alanine hydrochloride is also employed in research and development activities related to organic chemistry and drug discovery. Its versatile nature makes it an ideal candidate for exploring new chemical reactions and pathways, potentially leading to the discovery of novel compounds with therapeutic potential.
Used in Laboratory Settings:
In laboratories, 3-phenyl-DL-alanine hydrochloride is used for educational purposes and as a reagent in various chemical reactions. Its high solubility in water and stability make it a convenient choice for experiments and demonstrations in teaching and research.
Used in Industrial Settings:
In the industrial sector, 3-phenyl-DL-alanine hydrochloride is utilized in the large-scale production of pharmaceuticals and other organic compounds. Its role as a chiral building block is crucial for the synthesis of enantiomerically pure compounds, which are essential for the development of effective and safe drugs.

Upstream product

• 79410-35-8 (2S)-2-azido-3-phenylpropanoic acid 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 35661-40-6 N-Fmoc L-Phe 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 1186048-83-8 desmocyclopeptide 
• 63-91-2 L-phenylalanine 
• 1334715-65-9 versicoloritide A 
• 1334715-68-2 versicoloritide B 
• 1334715-72-8 versicoloritide C 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 346611-16-3 (S)-2-(N,N-dibenzyl)amino-3-phenylpropanal diethyl acetal 
• 1544699-35-5 C₂₀H₂₅NO₃ 

Downstream Products

• 137282-27-0 (2S)-2-(1-oxo-2,3-dihydro-1H-benzisoquinolin-2-yl)-3-phenylpropionic acid 
• 94856-81-2 L-β-phenyl-α-alanine decyl ester hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 50300-49-7 Z-Ala-Ala-Phe-OH 
• 24955-20-2 Cbz-glycyl-leucyl-phenylalanine 
• 14825-82-2 L-phenylalanine-N-carboxyanhydride 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 
• 119590-67-9 (2S,2'S)-2,2'-(ethane-1,2-diylbis(azanediyl))bis(3-phenylpropanoic acid) 
• 500783-09-5 C₄₇H₄₆N₄O₄ 
• 501009-95-6 GGTI-2376 
• 151141-67-2 ethyl (2S,3'S)-2-(3'-benzyl-2'-oxopiperazin-1'-yl)-3-phenylpropanoate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 3081-24-1 H-Phe-OEt 
• 1202-31-9 (S)-2-hydrazinyl-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxybenzophenone

We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).

Asymmetric Synthesis of Functionalized Phenylalanine Derivatives via Rh-Catalyzed Conjugate Addition and Enantioselective Protonation Cascade

The asymmetric conjugate addition of arylboronic acids to N-phthalimidodehydroalanine 1i catalyzed by Rh(I)/L1a enables the facile preparation of chiral functionalized phenylalanines. The reaction proceeds by a conjugate addition and enantioselective protonation cascade, affording a rhodium enolate that undergoes re-face protonation. The reaction tolerates various arylboronic acids and can be used in the gram-scale synthesis of (S)-phenylalanine hydrochloride, demonstrating the reaction scope and the synthetic feasibility of the process.

Synthesis and anti-parasitic activity of C-benzylated (N-arylcarbamoyl)alkylphosphonate esters

Unexpected substituent-dependent regioselectivty challenges in the synthesis of C-benzylated (N-arylcarbamoyl)phosphonate esters have been resolved. The C-benzylated N-furfurylcarbamoyl derivative showed low micromolar PfLDH inhibition, while one of the C-benzylated N-arylcarbamoyl analogues was active against Nagana Trypanosoma brucei parasites which are responsible for African trypanosomiasis in cattle.

LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs

The transporter protein Large-neutral Amino Acid Transporter 1 (LAT-1, SLC7A5) is responsible for transporting amino acids such as tyrosine and phenylalanine as well as thyroid hormones, and it has been exploited as a drug delivery mechanism. Recently its role in cancer has become increasingly appreciated, as it has been found to be up-regulated in many different tumor types, and its expression levels have been correlated with prognosis. Substitution at the meta position of aromatic amino acids has been reported to increase affinity for LAT-1; however, the SAR for this position has not previously been explored. Guided by newly refined computational models of the binding site, we hypothesized that groups capable of filling a hydrophobic pocket would increase binding to LAT-1, resulting in improved substrates relative to parent amino acid. Tyrosine and phenylalanine analogs substituted at the meta position with halogens, alkyl and aryl groups were synthesized and tested in cis-inhibition and trans-stimulation cell assays to determine activity. Contrary to our initial hypothesis we found that lipophilicity was correlated with diminished substrate activity and increased inhibition of the transporter. The synthesis and SAR of meta-substituted phenylalanine and tyrosine analogs is described.

LAT1 activity of carboxylic acid bioisosteres: Evaluation of hydroxamic acids as substrates

Large neutral amino acid transporter 1 (LAT1) is a solute carrier protein located primarily in the blood–brain barrier (BBB) that offers the potential to deliver drugs to the brain. It is also up-regulated in cancer cells, as part of a tumor's increased metabolic demands. Previously, amino acid prodrugs have been shown to be transported by LAT1. Carboxylic acid bioisosteres may afford prodrugs with an altered physicochemical and pharmacokinetic profile than those derived from natural amino acids, allowing for higher brain or tumor levels of drug and/or lower toxicity. The effect of replacing phenylalanine's carboxylic acid with a tetrazole, acylsulfonamide and hydroxamic acid (HA) bioisostere was examined. Compounds were tested for their ability to be LAT1 substrates using both cis-inhibition and trans-stimulation cell assays. As HA-Phe demonstrated weak substrate activity, its structure–activity relationship (SAR) was further explored by synthesis and testing of HA derivatives of other LAT1 amino acid substrates (i.e., Tyr, Leu, Ile, and Met). The potential for a false positive in the trans-stimulation assay caused by parent amino acid was evaluated by conducting compound stability experiments for both HA-Leu and the corresponding methyl ester derivative. We concluded that HA's are transported by LAT1. In addition, our results lend support to a recent account that amino acid esters are LAT1 substrates, and that hydrogen bonding may be as important as charge for interaction with the transporter binding site.

Recyclable Ligands for the Non-Enzymatic Dynamic Kinetic Resolution of Challenging α-Amino Acids

Structurally simple and inexpensive chiral tridentate ligands were employed for substantially advancing the purely chemical dynamic kinetic resolution (DKR) of unprotected racemic tailor-made α-amino acids (TM-α-AAs), enabling the first DKR of TM-α-AAs bearing tertiary alkyl chains as well as multiple unprotected functional groups. Owing to the operationally convenient conditions, virtually complete stereoselectivity, and full recyclability of the source of chirality, this method should find wide applications for the preparation of TM-α-AAs, especially on large scale. The non-enzymatic dynamic kinetic resolution of racemic α-amino acids bearing tertiary alkyl chains and multiple unprotected functional groups is based on the enantioselective formation of nickel(II) complexes and their hydrolysis under convenient conditions. The specially designed chiral ligands are inexpensive and can be quantitatively recycled.

Organocatalytic asymmetric biomimetic transamination of α-keto acetals to chiral α-amino acetals

This paper describes a chiral base-catalyzed asymmetric biomimetic transamination of α-keto acetals. A wide variety of α-amino acetals containing various functional groups can be synthesized in 50-85% yield and 82-86% ee.

Asymmetric chemoenzymatic synthesis of N-acetyl-α-amino esters based on lipase-catalyzed kinetic resolutions through interesterification reactions

Several phenylalanine analogs have been synthesized through a four-step route starting from easily available ethyl acetamidocyanoacetate. In a first reaction, and making use of phase transfer catalysts, this compound reacted with several alkyl halides, being benzyltributylammonium chloride identified as the best one for the production of a series of quaternary amino acids in moderate to excellent yields (52-95%). Then, the corresponding N-acetyl-phenylalanine methyl and allyl ester derivatives were obtained through acidic hydrolysis, esterification, and N-acetylation. Rhizomucor miehei lipase was found as a versatile enzyme for the resolution of these amino esters, finding the best results through interesterification reactions with butyl butyrate in acetonitrile. A great influence in the stereoselectivity was found depending on the chemical structure of the compound, achieving for the non- or para-substituted in the phenyl ring excellent stereoselectivities, being moderate for the meta-nitro derivative, while the ortho-nitro amino ester did not react.

Isolation and structural determination of the antifouling diketopiperazines from marine-derived Streptomyces praecox 291-11

Marine derived actinomycetes constituting 185 strains were screened for their antifouling activity against the marine seaweed, Ulva pertusa, and fouling diatom, Navicula annexa. Strain 291-11 isolated from the seaweed, Undaria pinnatifida, rhizosphere showed the highest antifouling activity and was identified as Streptomyces praecox based on a 16S rDNA sequence analysis. Strain 291-11 was therefore named S. praecox 291-11. The antifouling compounds from S. praecox 291-11 were isolated, and their structures were analyzed. The chemical constituents representing the antifouling activity were identified as (6S,3S)-6-benzyl-3-methyl-2,5-diketopiperazine (bmDKP) and (6S,3S)-6-isobutyl-3- methyl-2,5-diketopiperazine (imDKP) by interpreting the nuclear magnetic resonance and high-resolution mass spectroscopy data. Approximately 4.8mg of bmDKP and 3.1 mg of imDKP were isolated from 1.2 g of the S. praecox 291-11 crude extract. Eight different compositions of culture media were investigated for culture, the TBFeC medium being best for bmDKP and TCGC being the optimum for imDKP production. Two compounds respectively showed a 17.7 and 21 therapeutic ratio (LC50/EC50) to inhibit zoospores, and two compounds respectively showed a 263 and 120.2 therapeutic ratio to inhibit diatoms.

Preparation of chiral amino esters by asymmetric phase-transfer catalyzed alkylations of schiff bases in a ball mill

The asymmetric alkylation of Schiff bases under basic conditions in a ball mill was performed. The starting Schiff bases of glycine were prepared beforehand by milling protected glycine hydrochloride and benzophenone imine, in the absence of solvent. The Schiff base was then reacted with a halogenated derivative in a ball mill in the presence of KOH. By adding a chiral ammonium salt derived from cinchonidine, the reaction proceeded asymmetrically under phase-transfer catalysis conditions, giving excellent yields and enantiomeric excesses up to 75 %. Because an equimolar amount of starting material was used, purification was greatly simplified. Copyright