4801-80-3

Basic information

• Product Name: Z-PHE-NH2
• Synonyms: N-ALPHA-CBZ-L-PHENYLALANINE AMIDE;N-ALPHA-CARBOBENZOXY-L-PHENYLALANINE AMIDE;Z-L-PHENYLALANINE AMIDE;Z-PHENYLALANINE-NH2;Z-PHE-NH2;N-alpha-Benzyloxycarbonyl-L-phenylalanine amide;Z-L-Phe-NH2;CBZ-L-PHENYLALANINE AMIDE
• CAS NO: 4801-80-3
• Molecular Formula: C₁₇H₁₈N₂O₃
• Molecular Weight: 298.34
• Mol File: 4801-80-3.mol
• Article Data: 40

Chemical Properties

• Melting Point: 165-166 °C(Solv: chloroform (67-66-3); heptane (142-82-5))
• Boiling Point: 356.9oC at 760 mmHg
• Flash Point: 169.7oC
• Appearance: /Solid
• Density: 1.143 g/cm3
• Storage Temp.: Store at RT.
• PKA: 11.13±0.46(Predicted)
• CAS DataBase Reference: Z-PHE-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: Z-PHE-NH2(4801-80-3)
• EPA Substance Registry System: Z-PHE-NH2(4801-80-3)

Safety Data

• Hazardous Substances Data: 4801-80-3(Hazardous Substances Data)

Usage

Description

Z-PHE-NH2, also known as carbobenzoxy-L-phenylalanine, is a complex organic compound that is widely used in scientific research, particularly in the fields of medicinal chemistry and organic synthesis. It is a member of the phenylalanine family and derivatives, which are aromatic compounds containing the phenylalanine moiety. Z-PHE-NH2 is valued for its active component, the phenylalanine moiety, which is instrumental in the preparation of various peptide-based drugs.

Uses

Used in Pharmaceutical Industry:
Z-PHE-NH2 is used as a protecting agent for the amino group during peptide synthesis. Its role is crucial in ensuring the successful conjugation of amino acids, which is a fundamental process in the creation of peptide-based drugs.
Used in Medicinal Chemistry Research:
In the context of medicinal chemistry, Z-PHE-NH2 serves as a valuable component in the synthesis of new drug molecules. Its presence in the structure of these compounds can contribute to their therapeutic properties and potential applications in treating various diseases.
Used in Organic Synthesis:
Z-PHE-NH2 is also utilized in organic synthesis, where it can be incorporated into the structure of complex organic molecules. This can lead to the development of new compounds with unique chemical properties and potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 3081-24-1 H-Phe-OEt 
• 501-53-1 benzyl chloroformate 
• 1161-13-3 N-Cbz-L-Phe 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 541-41-3 chloroformic acid ethyl ester 
• 54769-22-1 1-methanesulfonyloxy-1,2,3-benzotriazole 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 543-27-1 isobutyl chloroformate 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 5241-58-7 L-Phenylalanine amide 
• 39608-52-1 benzyl carbonochloridate 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 928406-57-9 {(S)-1-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-carbamoyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester 
• 928406-70-6 {(S)-1-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-carbamoyl-propylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester 

Downstream Products

• 208665-37-6 2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-oxo-butyric acid methyl ester 
• 208665-36-5 2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-malonic acid dimethyl ester 
• 144774-94-7 [(S)-1-(4-Hydroxy-4,5-dihydro-thiazol-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 1314777-91-7 (S,Z)-benzyl 1-(1-hydroxybut-2-en-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 
• 872721-00-1 Fmoc-PheΨ(NHCO)Gly-OBu 
• 1402832-87-4 Fmoc-Phe-Ψ(NHCO)-Gly-OH 

Relevant articles and documents

Synthesis of Terminal Thiazoles from N-Protected Amino Acids and a Study of Their Antibacterial Activities

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Synthesis and Preclinical Evaluation of the First Carbon-11 Labeled PET Tracers Targeting Substance P1-7

Two potent SP1-7 peptidomimetics have been successfully radiolabeled via [11C]CO2-fixation with excellent yields, purity, and molar activity. l-[11C]SP1-7-peptidomimetic exhibited promising ex vivo biodistribution profile. Metabolite analysis showed that l-[11C]SP1-7-peptidomimetic is stable in brain and spinal cord, whereas rapid metabolic degradation occurs in rat plasma. Metabolic stability can be significantly improved by substituting l-Phe for d-Phe, preserving 70% more of intact tracer and resulting in better brain and spinal cord tracer retention. Positron emission tomography (PET) scanning confirmed moderate brain (1.5 SUV; peak at 3 min) and spinal cord (1.0 SUV; peak at 10 min) uptake for l- and d-[11C]SP1-7-peptidomimetic. A slight decrease in SUV value was observed after pretreatment with natural peptide SP1-7 in spinal cord for l-[11C]SP1-7-peptidomimetic. On the contrary, blocking using cold analogues of l- and d-[11C]tracers did not reduce the tracers' brain and spinal cord exposure. In summary, PET scanning of l- and d-[11C]SP1-7-peptidomimetics confirms rapid blood-brain barrier and blood-spinal-cord barrier penetration. Therefore, further validation of these two tracers targeting SP1-7 is needed in order to define a new PET imaging target and select its most appropriate radiopharmaceutical.

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.