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

• 4801-69-8 N-Benzyloxycarbonyl-L-phenylalanin- 
• 928406-59-1 [(S)-1-((S)-1-Amino-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 127-88-8 N,N-di(2-chloroethyl)amidophosphoric acid dichloride 
• 928406-72-8 [(S)-1-((R)-1-Amino-3-hydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 541-41-3 chloroformic acid ethyl ester 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 39608-52-1 benzyl carbonochloridate 
• 5241-58-7 L-Phenylalanine amide 
• 501-53-1 benzyl chloroformate 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 543-27-1 isobutyl chloroformate 

Downstream Products

• 1314777-91-7 (S,Z)-benzyl 1-(1-hydroxybut-2-en-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 
• 1374746-33-4 C₂₅H₃₃N₃O₅ 
• 21933-50-6 (S)-2-phenyl-1-(1H-tetrazol-5-yl)ethan-1-amine 
• 1471452-97-7 C₉H₁₁N₅*C₂HF₆NO₄S₂ 
• 47365-05-9 benzyl (S)-(2-phenyl-1-(1H-tetrazol-5-yl)ethyl)carbamate 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 18942-49-9 Boc-D-Phe-OH 
• 63-91-2 L-phenylalanine 
• 15366-16-2 H-Trp-Nle-Asp-Phe-NH₂ 
• 5241-67-8 H-Asp(O-tBu)-Phe-NH₂ 
• 944914-09-4 (4S,5S)-4-(2-hydroxyethyl)-1,5-bis(phenylmethyl)-imidazolidin-2-one 

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.

Optimization and Structure-Activity Relationships of Phosphinic Pseudotripeptide Inhibitors of Aminopeptidases That Generate Antigenic Peptides

The oxytocinase subfamily of M1 aminopeptidases, consisting of ER aminopeptidase 1 (ERAP1), ER aminopeptidase 2 (ERAP2), and insulin-regulated aminopeptidase (IRAP), plays critical roles in the generation of antigenic peptides and indirectly regulates human adaptive immune responses. We have previously demonstrated that phosphinic pseudotripeptides can constitute potent inhibitors of this group of enzymes. In this study, we used synthetic methodologies able to furnish a series of stereochemically defined phosphinic pseudotripeptides and demonstrate that side chains at P1′ and P2′ positions are critical determinants in driving potency and selectivity. We identified low nanomolar inhibitors of ERAP2 and IRAP that display selectivity of more than 2 and 3 orders of magnitude, respectively. Cellular analysis demonstrated that one of the compounds that is a selective IRAP inhibitor can reduce IRAP-dependent but not ERAP1-dependent cross-presentation by dendritic cells with nanomolar efficacy. Our results encourage further preclinical development of phosphinic pseudotripeptides as regulators of adaptive immune responses.