53562-23-5

Basic information

• Product Name: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester
• CAS NO: 53562-23-5
• Molecular Formula: C17H18N2O3
• Molecular Weight: 298.342
• Mol File: 53562-23-5.mol
• Article Data: 42

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester(53562-23-5)
• EPA Substance Registry System: Carbamic acid, [2-amino-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester(53562-23-5)

Safety Data

• Hazardous Substances Data: 53562-23-5(Hazardous Substances Data)

Upstream product

• 3081-24-1 H-Phe-OEt 
• 501-53-1 benzyl chloroformate 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1161-13-3 N-Cbz-L-Phe 
• 541-41-3 chloroformic acid ethyl ester 
• 3588-57-6 Z-DL-Phe-OH 
• 39608-52-1 benzyl carbonochloridate 
• 5241-58-7 L-Phenylalanine amide 
• 108321-83-1 phenylalanine amide hydrochloride 
• 150-30-1 Phenylalanine 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 

Downstream Products

• 5241-57-6 L-phenylalaninamide acetate salt 
• 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 
• 130457-33-9 [1-(1-Benzotriazol-1-yl-2-methyl-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 102582-52-5 N-carbobenzoxy-L-phenylalanyl-D,L-2-hydroxyglycinebenzylester 
• 13238-73-8 Z-DL-Phenylalanin-thiono-ethylester 
• 125453-42-1 [1-(1-Amino-2-methyl-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 109522-26-1 2-(benzyloxycarbonylamino)-3-phenyl-propionitrile 
• 113586-09-7 Z-D,L-Phe-ΔVal 
• 113586-13-3 (Z)-Z-Phe-Δ Leu 
• 113586-05-3 (Z)-Z-Phe-Δ Abu 
• 113586-16-6 (E/Z)-Z-Phe-Δ Ile 

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.