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Usage

Uses

Used in Pharmaceutical Industry:
L-Phenylalanine is utilized as a key component in the production of various pharmaceuticals. Its role as a precursor to important neurotransmitters makes it a valuable ingredient in formulations for the treatment of depression and attention deficit hyperactivity disorder (ADHD). By enhancing the synthesis of mood-regulating neurotransmitters, L-Phenylalanine contributes to the effectiveness of these medications.
Used in Dietary Supplements:
As an essential amino acid, L-Phenylalanine is often included in dietary supplements to support overall health and well-being. It can help individuals who may not be getting enough of this nutrient from their diet, ensuring that their bodies have the necessary building blocks for protein synthesis and neurotransmitter production.
Used in Food Industry:
L-Phenylalanine is also used in the food industry, where it serves as a flavor enhancer and additive. Its ability to improve the taste and aroma of certain products makes it a popular choice for manufacturers looking to enhance the sensory qualities of their offerings.
Used in Cosmetics Industry:
In the cosmetics industry, L-Phenylalanine is employed as a precursor to the amino acid tyrosine, which is essential for the production of melanin, the pigment responsible for skin color. By promoting melanin synthesis, L-Phenylalanine can be used in formulations that aim to improve skin tone and provide a more even complexion.
Used in Research and Development:
L-Phenylalanine is also an important compound in research and development, particularly in the fields of neuroscience and biochemistry. Its role in neurotransmitter synthesis and its involvement in various metabolic pathways make it a valuable tool for studying the underlying mechanisms of mood regulation, stress response, and other physiological processes.

Upstream product

• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 393588-04-0 (2R,3R,αR)-2-hydroxy-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanol 
• 116911-14-9 (2S,3S)-3-azido-3-phenyl-propane-1,2-diol 
• 177723-18-1 (S)-2-(diphenylmethyl)amino-2-phenylacetonitrile 
• 1313219-11-2 (S,S)-α-phenyl-α-[1-(4-methoxyphenyl)ethylamino]acetonitrile hydrochloride 
• 2935-35-5 (S)-2-phenylglycine 
• 393588-13-1 (2R,αR)-2-phenyl-2-(N-benzyl-N-α-methylbenzylamino)ethanoic acid 
• 226388-27-8 (R)-α-(N,N-dibenzylamino)-α-phenylacetic acid 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 
• 144744-23-0 (3R,5S,6R)-2,3,5,6-Tetrahydro-3,5,6-triphenyl-1,4-oxazin-2-one 
• 64641-81-2 (S)-Phenyl-{[1-phenyl-meth-(E)-ylidene]-amino}-acetonitrile 
• 29129-67-7 (S)-2-azido-2-phenylacetic acid 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 127383-03-3 (3R,5R,6S)-4-(tert-Butoxycarbonyl)-2,3,5,6-tetrahydro-3,5,6-triphenyl-1,4-oxazin-2-one 

Downstream Products

• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 

Relevant academic research and scientific papers

Stereoselectivity in the salt-cocrystal products formed by phenylglycinol or phenylglycine with their respective sodium or hydrochloride salts

The salt and stereoselective cocrystal phenomena associated with 2-phenylglycinol and 2-phenylglycine have been studied using X-ray powder diffraction and differential scanning calorimetry. The chiral identities of the free acids and their sodium salts, or the free bases and their chloride salts, were found to play a determining role as to whether a salt-cocrystal product could or could not be formed. In particular, when cocrystallization of an enantiomerically pure basic or zwitterionic substance with its enantiomerically pure acid addition salt was attempted, a salt-cocrystal was only obtained when the absolute configuration of the two reactants is opposite. On the other hand, it has been found that no stereoselectivity in salt-cocrystal formation existed in the cocrystallization of an enantiomerically pure acidic or zwitterionic substance with its enantiomerically pure base addition salt. Copyright

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.

Asymmetric strecker synthesis of α-arylglycines

A practically simple three-component Strecker reaction for the asymmetric synthesis of enantiopure α-arylglycines has been developed. Addition of a range of aryl-aldehydes to a solution of sodium cyanide and (S)-1-(4- methoxyphenyl)ethylamine affords highly crystalline (S,S)-α-aminonitriles that are easily obtained in diastereomerically pure form. Heating the resultant (S,S)-α-aminonitriles in 6 M aqueous HCl at reflux resulted in cleavage of their chiral auxiliary fragments and concomitant hydrolysis of their nitrile groups to afford enantiopure (S)-α-arylglycines. The enantiopurities of these (S)-α-arylglycines were determined via derivatization of their corresponding methyl esters with 2-formylphenylboronic acid and (S)-BINOL, followed by 1H NMR spectroscopic analysis of the resultant mixtures of diastereomeric iminoboronate esters.

A practical synthesis of optically active arylglycines via catalytic asymmetric Strecker reaction

A practical procedure for catalytic asymmetric synthesis of optically active arylglycine derivatives via optically active α-aminonitriles has been developed. The N-benzhydryl α-arylaminonitrile intermediates were prepared in excellent yield (89-99%) and enantiomeric purity (96 to >98% ee) by enantioselective cyanation of aldimines with TMSCN/iPrOH in the presence of 2.5 mol % of an easily prepared Ti/chiral amino alcohol complex at 0 °C, without requiring slow addition of the cyanating agent. The easily racemized α-aminonitrile intermediates were efficiently hydrolyzed by an aqueous HCl/TFA mixture to give the arylglycine derivatives in good yield (60-92%) and moderate to excellent enantiomeric purity (85-98% ee).

Chemo-enzymatic dynamic kinetic resolution of amino acid thioesters

The L-forms of racemic-N-protected-β,γa,aunsaturated a-amino acid thioesters were found to be substrates for the subtilisin-catalysed hydrolysis to the corresponding acids. The D-enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracemisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities were achieved.

Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

An efficient protocol for the transformation of homochiral α-hydroxy-β-amino esters to their α-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino 1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-α-methylbenzyl protected α-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the α-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides α-amino acids in 94-98% e.e.

Asymmetric synthesis of α-amino carbonyls (aldehydes, ketones and acids) using lithium (R)-N-benzyl-N-α-methylbenzylamide

The diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to α,β-unsaturated esters and subsequent enolate hydroxylation, followed by reduction and oxidative cleavage provides a facile route to N,N-protected α-amino aldehydes and ketones. Further manipulation furnishes α-amino acids in high enantiomeric excess.

(R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries in the enantioselective preparation of α-amino acids

rac-α-Amino acids (rac-1a-d) were formally deracemized by a four-step reaction sequence: (a) protection of the amino function as the phthalimido derivative; (b) acyl chloride formation; (c) diastereoselective reaction with the chiral auxiliaries (R)- or (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2- pyrrolidinone, (R)- or (S)-3; and (d) acid hydrolysis to deprotect both the ester and phthalimido functions. Diastereoselectivities of the intermediate esters 4 were good (82-96% d.e.), except for the case of 4b (41% d.e.), the precursor of valine. The main diastereoisomer of esters 4 was (αR,3S)- or (αS,3R)-, except for 4d: in this case, working at -78°C, the (αR,3R)- diastereoisomer was the main product, which epimerizes easily at the α- position when at room temperature. Acid hydrolysis of esters 4 directly gave the deprotected α-amino acids, with little or no epimerization at the α- position of the α-amino acid and complete recovery of the chiral auxiliary. Only (αR,3R)-4d on acid hydrolysis partially epimerized at the α-position. Moreover, some α-amino acids and their N,N-dibenzyl derivatives were obtained by dynamic kinetic resolution of diastereoisomeric mixtures of α- bromo esters 5 derived from the chiral auxiliaries (R)- or (S)-3 during reaction with dibenzylamine.

Empirical rules for the enantiopreference of lipase from Aspergillus niger toward secondary alcohols and carboxylic acids, especially α-amino acids

Lipase from Aspergillus niger (ANL, Amano lipase AP) catalyzes enantioselective hydrolysis and acylation reactions. To aid in the design of new applications of this lipase, we propose two empirical rules that predict which enantiomer reacts faster. For secondary alcohols, a rule proposed previously for other lipases also works for ANL, but with lower reliability (77%, 37 of 48 examples). For carboxylic acids, we examined both crude and partially-purified ANL because commercial ANL contains contaminating hydrolases. Partial purification removed a contaminating amidase and increased the enantioselectivity of ANL toward many α-amino acids, including cyclic amino acids. Unlike other lipases, ANL readily accepts positively-charged substrates and shows the highest enantioselectivity towards α-amino acids. Although a rule based on the sizes of the substituents could not predict the fast-reacting enantiomer, a rule limited to α-amino acids did predict the fast-reacting enantiomer. We estimate that the charged α-amino group contributes a factor of 40-100 (ΔΔ≠ = 2.2-2.7 kcal/mol) to the enantioselectivity of ANL towards carboxylic acids.