2448-45-5

Basic information

• Product Name: N-Cbz-D-Phenylalanine
• Synonyms: CBZ-D-PHE;CBZ-D-PHENYLALANINE;CBZ-D-PHE-OH;BENZYLOXYCARBONYL-D-PHENYLALANINE;N-CBZ-D-PHENYLALANINE;N-CARBOBENZYLOXY-D-PHENYLALANINE;N-ALPHA-BENZYLOXYCARBONYL-D-PHENYLALANINE;N-ALPHA-CARBOBENZOXY-D-PHENYLALANINE
• CAS NO: 2448-45-5
• Molecular Formula: C₁₇H₁₇NO₄
• Molecular Weight: 299.32
• EINECS: 258-154-1
• Product Categories: AMINOACIDS DERIVATIVES;Amino Acid Derivatives;Phenylalanine [Phe, F];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Cbz-Amino acid series
• Mol File: 2448-45-5.mol

Chemical Properties

• Melting Point: 85-88 °C
• Boiling Point: 511.5 °C at 760 mmHg
• Flash Point: 263.1 °C
• Appearance: /
• Density: 1.248 g/cm³
• Vapor Pressure: 2.76E-11mmHg at 25°C
• Refractive Index: -5.3 ° (C=4, AcOH)
• Storage Temp.: −20°C
• PKA: 3.86±0.10(Predicted)
• Water Solubility: Soluble in methanol. Slightly soluble in water.
• BRN: 2817463
• CAS DataBase Reference: N-Cbz-D-Phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-D-Phenylalanine(2448-45-5)
• EPA Substance Registry System: N-Cbz-D-Phenylalanine(2448-45-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2448-45-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Cbz-D-Phenylalanine is used as an intermediate in the synthesis of various pharmaceutical compounds for its role in the production of catecholamines, which are essential for the proper functioning of the central nervous system.
Used in Research and Development:
N-Cbz-D-Phenylalanine is utilized as a research compound for studying the effects of D-Phenylalanine on stress-induced analgesia and its potential as an anti-enkephalinase agent, contributing to the development of new therapeutic approaches for stress-related conditions and pain management.
Used in Neurochemistry:
N-Cbz-D-Phenylalanine is employed in neurochemical research to understand the role of D-Phenylalanine in the biosynthesis of catecholamines, which are neurotransmitters involved in various physiological processes, including mood regulation, attention, and stress response.
Used in Drug Delivery Systems:
N-Cbz-D-Phenylalanine can be used in the development of drug delivery systems, particularly for targeting the central nervous system, due to its role in catecholamine synthesis and its potential to modulate stress response and pain perception.

InChI:InChI=1/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m1/s1

Upstream product

• 673-06-3 D-(R)-phenylalanine 
• 501-53-1 benzyl chloroformate 
• 64-17-5 ethanol 
• 3588-57-6 Z-DL-Phe-OH 
• 2578-86-1 DL-N-(carbobenzoxy)phenylalanine p-nitrophenyl ester 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 2578-85-0 p-nitrophenyl N-(benzyloxycarbonyl)-D-phenylalaninate 
• 63219-70-5 N-(benzyloxycarbonyl)-D-phenylalaninal 
• 91841-62-2 Boc-D-Phe-OPet 
• 174758-00-0 (R)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid 4-nitro-benzyl ester 
• 32563-40-9 methyl 2-(((benzyloxy)carbonyl)amino)-3-phenylpropanoate 
• 150-30-1 Phenylalanine 
• 565234-20-0 benzyl (2S,3R,5R)-5-benzyl-2,3-dimethoxy-2,3-dimethyl-6-oxomorpholine-4-carboxylate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 122411-93-2 N-benzyloxycarbonyl-phenylalanyl=>glycyl=>valine ethyl ester; N-benzyloxycarbonyl-D-phenylalanyl=>glycyl=>D-valine ethyl ester 
• 119659-55-1 N-benzyloxycarbonyl-phenylalanyl=>glycyl=>alanine ethyl ester; N-benzyloxycarbonyl-D-phenylalanyl=>glycyl=>L-alanine ethyl ester 
• 30507-68-7 N-benzyloxycarbonyl-phenylalanyl=>glycyl=>alanine ; N-benzyloxycarbonyl-D-phenylalanyl=>glycyl=>D-alanine 
• 58607-69-5 D-phenylalaninyl-D-phenylalanine 
• 17257-55-5 N-(N-benzyloxycarbonyl-D-phenylalanyl)-L-phenylalanine ethyl ester 
• 51926-52-4 D-Phe-L-Pro 
• 2578-85-0 p-nitrophenyl N-(benzyloxycarbonyl)-D-phenylalaninate 
• 1436-74-4 Z-D-Phe-ε-Z-L-Lys-OEt 
• 63655-58-3 Z-D-Phe-Ser-OMe 
• 112924-08-0 tert-butyl N-(benzyloxycarbonyl)-D-phenylalaninate 
• 114645-17-9 (3R)-1-diazo-3-(N-benzyloxycarbonylamino)-4-phenyl-2-butanone 
• 62023-23-8 [(R)-1-Benzyl-2-(3,5-dimethyl-pyrazol-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester 
• 91841-62-2 Boc-D-Phe-OPet 
• 3397-36-2 (R)-N-(benzyloxycarbonyl)phenylalanine N-hydroxysuccinimidyl ester 

Relevant articles and documents

Chemical dynamic kinetic resolution and S/R interconversion of unprotected α-amino acids

Reported herein is the first purely chemical method for the dynamic kinetic resolution (DKR) of unprotected racemic α-amino acids (α-AAs), a method which can rival the economic efficiency of the enzymatic reactions. The DKR reaction principle can be readily applied for S/R interconversions of α-AAs, the methodological versatility of which is unmatched by biocatalytic approaches. The presented process features a virtually complete stereochemical outcome, fully recyclable source of chirality, and operationally simple and convenient reaction conditions, thus allowing its ready scalability. A quite unique and novel mode of the thermodynamic control over the stereochemical outcome, including an exciting interplay between axial, helical, and central elements of chirality is proposed. A new player for DKR: Dynamic kinetic resolution of α-amino acids has been achieved upon complexation with nickel(II) and a chiral ligand derived from optically active bis(naphthyl)amine under thermodynamic control, thus affording excellent diastereoselectivities and chemical yields. The S to R interconversion of α-amino acids is also described.

Tetracyclic compound as plasma kallikrein inhibitor and application thereof

The invention provides a tetracyclic plasma kallikrein inhibitor compound which is novel in structure, good in activity and high in selectivity, and can be widely applied to prevention or treatment of diseases related to plasma kallikrein activity.

Tricyclic compound as plasma kallikrein inhibitor and application thereof

The invention provides a tricyclic plasma kallikrein inhibitor compound which is novel in structure, good in activity and high in selectivity. The tricyclic plasma kallikrein inhibitor compound can be widely applied to prevention or treatment of diseases related to plasma kallikrein activity.

Tetracyclic compound as plasma kallikrein inhibitor and application thereof

The invention provides a tetracyclic plasma kallikrein inhibitor compound which is novel in structure, good in activity and high in selectivity, and can be widely applied to prevention or treatment of diseases related to plasma kallikrein activity.

Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin

Enantioselective inclusion of α-amino acids with crystals of α-cyclodextrin (α-CD) has been achieved by converting the amino acids into sulfonate salts with pyrene-1-sulfonic acid (PyS). For example, crystals of α-CD selectively include L-leucine/PyS (1:1) salt in a host/guest ratio of ～1 with 92%ee from a solution of the racemic salt in ethanol/N-methylformamide (91:9) at 40 °C. Under conditions optimized for individual amino acids, the PyS salts of valine, phenylalanine, and methionine are also included with good enantioselectivities (up to 86%ee). Mechanistic studies for the inclusion of leucine/PyS salt reveals that the enantioselectivity originates from the difference in stability between the inclusion complexes of D- and L-leucine/PyS salts with α-CD in crystals.

β,γ-diamino acids as building blocks for new analogues of Gramicidin S: Synthesis and biological activity

We describe here the synthesis and biological activity study of a pair of diastereomeric analogues of Gramicidin S using β,γ-diamino acids as β-turn mimic. The synthesis of the orthogonally protected β,γ-diamino acids was achieved in 6 steps starting from D-alanine. The analogues were then synthesized in solution phase and on solid phase. Biological activity tests showed that, compared with Gramicidin S, both analogues exerted diminished hemolytic activity while they retained interesting antibacterial activity.

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

Substrate specificity of an actively assembling amyloid catalyst

In the presence of Zn2+, the catalytic, amyloid-forming peptide Ac-IHIHIQI-NH2, was found to exhibit enhanced selectivity for hydrophobic p-nitrophenyl ester substrates while in the process of self-assembly. As opposed to the substrate p-nitrophenyl acetate, which was more effectively hydrolyzed with Ac-IHIHIQI-NH2 in its fully fibrillar state, the hydrophobic substrate Z-L-Phe-ONp was converted with a second-order rate constant more than 11-times greater when the catalyst was actively assembling. Under such conditions, Z-L-Phe-ONp hydrolysis proceeded at a greater velocity than the more hydrophilic and otherwise more labile ester Boc-L-Asn-ONp. When assembling, the catalyst also showed increased selectivity for the L-enantiomer of Z-Phe-ONp. These findings suggest the occurrence of increased interactions of hydrophobic moieties of the substrate with exposed hydrophobic surfaces of the assembling peptides and present valuable features for future de novo design consideration.

Novel Analogues of (R)-5-(Methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (Sumanirole) Provide Clues to Dopamine D2/D3 Receptor Agonist Selectivity

Novel 1-, 5-, and 8-substituted analogues of sumanirole (1), a dopamine D2/D3 receptor (D2R/D3R) agonist, were synthesized. Binding affinities at both D2R and D3R were higher when determined in competition with the agonist radioligand [3H]7-hydroxy-N,N-dipropyl-2-aminotetralin (7-OH-DPAT) than with the antagonist radioligand [3H]N-methylspiperone. Although 1 was confirmed as a D2R-preferential agonist, its selectivity in binding and functional studies was lower than previously reported. All analogues were determined to be D2R/D3R agonists in both GoBRET and mitogenesis functional assays. Loss of efficacy was detected for the N-1-substituted analogues at D3R. In contrast, the N-5-alkyl-substituted analogues, and notably the n-butyl-arylamides (22b and 22c), all showed improved affinity at D2R over 1 with neither a loss of efficacy nor an increase in selectivity. Computational modeling provided a structural basis for the D2R selectivity of 1, illustrating how subtle differences in the highly homologous orthosteric binding site (OBS) differentially affect D2R/D3R affinity and functional efficacy.

Glycosylation mediated - BAIL in aqueous solution

The use of Br?nsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution.