92455-53-3

Basic information

• Product Name: Z-D-TYR(BZL)-OH
• Synonyms: N-[(Phenylmethoxy)carbonyl]-O-(phenylmethyl)-D-tyrosine;Z-O-benzyl-D-tyrosine≥ 99% (HPLC);N-ALPHA-CARBOBENZOXY-D-TYROSINE O-BENZYL ETHER;N-ALPHA-CBZ-O-BENZYL-D-TYROSINE;Z-D-TYR(BZL)-OH;Z-D-TYROSINE(BZL)-OH;Z-O-BENZYL-D-TYROSINE;CBZ-(R)-2-AMINO-3-(4'-BENZYLOXYPHENYL)PROPANOIC ACID
• CAS NO: 92455-53-3
• Molecular Formula: C₂₄H₂₃NO₅
• Molecular Weight: 405.44
• Product Categories: Amino Acid Derivatives
• Mol File: 92455-53-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 113-119℃
• Boiling Point: 624.4 °C at 760 mmHg
• Flash Point: 331.5 °C
• Appearance: White/Powder
• Density: 1.249 g/cm³
• Storage Temp.: Store at RT.
• CAS DataBase Reference: Z-D-TYR(BZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-D-TYR(BZL)-OH(92455-53-3)
• EPA Substance Registry System: Z-D-TYR(BZL)-OH(92455-53-3)

Safety Data

• Hazardous Substances Data: 92455-53-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 16652-64-5 O-benzyl-S-tyrosine 
• 501-53-1 benzyl chloroformate 
• 1164-16-5 Z-L-Tyr-OH 
• 100-39-0 benzyl bromide 
• 60-18-4 L-tyrosine 
• 315203-50-0 N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester 

Downstream Products

• 3562-03-6 Z-Tyr(OBzl)-ONp 
• 106629-52-1 N,N'-Bis-(O-benzyl-N-benzyloxycarbonyl-L-tyrosyl)-ethylendiamin 
• 52773-66-7 benzyloxycarbonyl-O-benzyl-L-tyrosine 1-succinimidyl ester 
• 90427-46-6 Z-Tyr(OBzl)-ONB 
• 81638-97-3 O-(N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-2-pyridylmethylketoxime 
• 225386-51-6 phenylmethyl (4S)-5-oxo-4-({4-[(phenylmethyl)oxy]phenyl}methyl)-1,3-oxazolidine-3-carboxylate 
• 315203-50-0 N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester 
• 854443-27-9 (2S,3S)-2-amino-1-(4-benzyloxyphenyl)-hex-5-en-3-ol 
• 854443-28-0 (2S,3S)-2-azido-1-(4-benzyloxyphenyl)-hex-5-en-3-ol 
• 854443-26-8 (4S,5S)-5-allyl-4-(4-benzyloxybenzyl)-oxazolidin-2-one 
• 854443-21-3 [(1S,2S)-2-azido-3-(4-benzyloxyphenyl)-1-(2-oxoethyl)-prop-1-oxy]-acetic acid tert-butyl ester 
• 854443-25-7 [(S)-1-(4-Benzyloxy-benzyl)-2-hydroxy-pent-4-enyl]-carbamic acid benzyl ester 
• 854443-24-6 (S)-2-benzyloxycarbonylamino-1-(4-benzyloxyphenyl)-hex-5-en-3-one 
• 854443-29-1 α-[(4S,5S)-5-azido-6-(4-benzyloxyphenyl)-1,2-dihydroxy-hex-4-oxy]-acetic acid tert-butyl ester 

Relevant articles and documents

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.

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.