478183-64-1

Basic information

• Product Name: BOC-D-PHE(2-I)-OH
• Synonyms: BOC-2-IODO-D-PHENYLALANINE;BOC-D-2-IODOPHENYLALANINE;BOC-D-PHE(2-I)-OH;BOC-O-IODO-D-PHE-OH;N-ALPHA-T-BUTOXYCARBONYL-D-(2-IODOPHENYL)ALANINE;(R)-2-(tert-butoxycarbonylamino)-3-(2-iodophenyl)propanoic acid
• CAS NO: 478183-64-1
• Molecular Formula: C14H18INO4
• Molecular Weight: 391.2
• Product Categories: Amino Acid Derivatives
• Mol File: 478183-64-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: BOC-D-PHE(2-I)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-PHE(2-I)-OH(478183-64-1)
• EPA Substance Registry System: BOC-D-PHE(2-I)-OH(478183-64-1)

Safety Data

• Hazardous Substances Data: 478183-64-1(Hazardous Substances Data)

Usage

General Description

BOC-D-PHE(2-I)-OH is a scientific organic chemical compound used primarily in chemical research and production. It's categorized as an amino acid derivative and it's more formally known as BOC-D-Phenylalanine(2-I)-OH. BOC-D-PHE(2-I)-OH is important in the field of chemistry and biochemistry, specifically in peptide synthesis where it's actively used. Further, the BOC in its name refers to the BOC-protecting group - BOC protects the amine group in the amino acid during the elongation step of peptide synthesis. Its IUPAC name is (2S)-2-amino-3-(2-iodo-4,5-dimethoxyphenyl)-2-methylpropanoic acid and the CAS number is 19883-10-4. It is typically a white to off-white solid and should be stored in a cool, dry place for optimum longevity.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 167817-55-2 2-I-L-Phe-OH 

Relevant articles and documents

2-[ 18 F]Fluorophenylalanine: Synthesis by Nucleophilic 18 F-Fluorination and Preliminary Biological Evaluation

2-[ 18 F]Fluorophenylalanine (2-[ 18 F]FPhe), a promising PET tracer for imaging of cerebral infarction and tumors, was efficiently prepared from an easily accessible iodonium salt precursor using Cu-mediated radiofluorination under 'low base' or 'minimalist' conditions. Whereas significant racemization was initially observed if the 'minimalist' protocol was applied for radiolabeling, it was completely suppressed by the careful adjustment of 18 F - preprocessing. The initial biological study revealed a higher uptake of 2-[ 18 F]FPhe in different tumor cells in comparison to that of [ 18 F]FET. In contrast to 4-[ 18 F]FPhe, which suffered from rapid defluorination in vivo, 2-[ 18 F]FPhe demonstrated a sufficient in vivo stability. Conclusively, 2-[ 18 F]FPhe is a promising PET probe that is now readily available using Cu-mediated radiofluorination under 'minimalist' or 'low base' conditions. The simplicity of the translation of the proposed procedures to automated synthesis modules allows a broad biological evaluation of 2-[ 18 F]FPhe. Notably, a novel protocol for the preparation of N -Boc protected amino acids from the respective Ni-Schiff base complexes was developed that avoided application of strongly acidic conditions.