273221-78-6

Basic information

• Product Name: BOC-PHE(2-I)-OH
• Synonyms: N-ALPHA-BUTOXYCARBONYL-2-IODO-L-PHENYLALANINE;BOC-L-2-IODOPHENYLALANINE;BOC-2-IODO-L-PHENYLALANINE;BOC-PHE(2-I)-OH;BOC-L-PHE(2-I);(S)-2-(tert-butoxycarbonylamino)-3-(2-iodophenyl)propanoic acid;Boc-L-Phe(2-I)-OH;(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(2-iodophenyl)propanoic acid
• CAS NO: 273221-78-6
• Molecular Formula: C₁₄H₁₈INO₄
• Molecular Weight: 391.2
• Mol File: 273221-78-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: BOC-PHE(2-I)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-PHE(2-I)-OH(273221-78-6)
• EPA Substance Registry System: BOC-PHE(2-I)-OH(273221-78-6)

Safety Data

• Hazardous Substances Data: 273221-78-6(Hazardous Substances Data)

Usage

General Description

BOC-PHE(2-I)-OH is a chemical compound that is commonly used in peptide synthesis. It is a derivative of BOC-PHE-OH, which is a protected form of the amino acid phenylalanine. The addition of the 2-I group indicates that a iodine atom is attached to the phenyl ring. This modification can be useful in facilitating specific interactions with other molecules, or in altering the properties of the peptide in which this amino acid is incorporated. BOC-PHE(2-I)-OH is often used as a building block in the synthesis of complex peptides and can be further modified to create a variety of peptide structures with different bioactivities and properties.

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.