24250-85-9

Basic information

• Product Name: L-4-Iodophenylalanine
• Synonyms: L-4-IODOPHE;L-4-IODOPHENYLALANINE;H-L-PHE(4-I)-OH;H-PHE(P-I)-OH;H-PHE(4-I)-OH;H-P-IODO-L-PHE-OH;H-P-IODO-PHE-OH;4-IODO-PHE-OH
• CAS NO: 24250-85-9
• Molecular Formula: C₉H₁₀INO₂
• Molecular Weight: 291.09
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Miscellaneous;Phenylalanine [Phe, F];Unusual Amino Acids;Chiral Compound
• Mol File: 24250-85-9.mol

Chemical Properties

• Melting Point: 255-256 °C
• Boiling Point: 366.8 °C at 760 mmHg
• Flash Point: 175.6 °C
• Appearance: /
• Density: 1.824 g/cm³
• Vapor Pressure: 5.01E-06mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: −20°C
• PKA: 2.19±0.10(Predicted)
• Water Solubility: Partly miscible with water.
• Sensitive: Light Sensitive
• BRN: 4411317
• CAS DataBase Reference: L-4-Iodophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: L-4-Iodophenylalanine(24250-85-9)
• EPA Substance Registry System: L-4-Iodophenylalanine(24250-85-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 24250-85-9(Hazardous Substances Data)

Usage

Uses

Used in Protein Engineering:
L-4-Iodophenylalanine is used as a model unnatural α-amino acid for altering the primary amino acid composition of proteins via the opal (UGA) codon. This allows for the introduction of new functionalities and properties to the engineered proteins, which can be beneficial in various research and commercial applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, L-4-Iodophenylalanine can be used as a building block for the synthesis of novel drugs, particularly those targeting specific receptors or enzymes. Its unique structure and properties can contribute to the development of more effective and selective therapeutic agents.
Used in Research and Development:
L-4-Iodophenylalanine is also used in research and development for studying protein structure, function, and interactions. It can be incorporated into proteins to investigate the effects of specific amino acid substitutions on protein stability, folding, and activity.
Used in Diagnostics:
In the diagnostics field, L-4-Iodophenylalanine can be employed as a label or marker for various analytical techniques, such as mass spectrometry or fluorescence-based assays. Its unique chemical properties make it suitable for tracking and detecting specific proteins or other biomolecules in complex biological samples.

InChI:InChI=1/C9H10INO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m1/s1

Upstream product

• 76410-58-7 p-borono-L-phenylalanine 
• 62040-55-5 p-amino-L-phenylalanine hydrochloride 
• 63-91-2 L-phenylalanine 
• 150-30-1 Phenylalanine 
• 16004-15-2 1-bromomethyl-4-iodobenzene 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 

Downstream Products

• 1173918-59-6 methyl 2-amino-3-(4-iodophenyl)propanoate hydrochloride 
• 82565-68-2 N-fmoc-4-iodo-(L)-phenylalanine 
• 278605-15-5 (S)-4-ethynylphenylalanine 
• 115820-04-7 N-trifluoroacetyl-4-iodophenylalanine 
• 222854-50-4 (L)-4-iodophenylalanine t-butyl ester 
• 262603-99-6 N,N-dibenzyl-4-iodo-L-phenylalanine benzyl ester 
• 220400-04-4 N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine 
• 79385-75-4 N-2-(p-biphenylyl)isopropoxycarbonyl-4-iodophenylalanine cyclohexylamine salt 
• 117161-23-6 (S)-2-Ethoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid 
• 103882-09-3 N-Boc-4-I-Phe-OH 
• 143508-14-9 (S)-2-[(R)-(1-Aza-bicyclo[2.2.2]oct-3-yl)amino]-3-(4-iodo-phenyl)-propionic acid 
• 143508-14-9 (S)-2-[(S)-(1-Aza-bicyclo[2.2.2]oct-3-yl)amino]-3-(4-iodo-phenyl)-propionic acid 

Relevant articles and documents

PRODUCTION METHOD FOR RADIOLABELED ARYL COMPOUND

The invention relates to a method of producing the radiolabeled aryl compound (I) Ar—X, or a salt thereof, wherein X is 211At, 210At, 123I, 124I, 125I, or 131I. The method involves reacting the aryl boronic acid compound (II) Ar—Y, or a salt thereof, wherein Y is a borono group (—B(OH)2) or an ester group thereof, with a radionuclide selected from 211At, 210At, 123I, 124I, 125I and 131I, in the presence of an oxidizing agent selected from an alkali metal iodide, an alkali metal bromide, N-bromosuccinimide, N-chlorosuccinimide and hydrogen peroxide, in water.

Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes

The development of a synthetic code that enables a sequence programmable feature like DNA represents a key aspect toward intelligent molecular systems. We developed herein the well-known dynamic covalent interaction between boronic acids (BAs) and catechols (CAs) into synthetic nucleobase analogs. Along a defined peptide backbone, BA or CA residues are arranged to enable sequence recognition to their complementary strand. Dynamic strand displacement and errors were elucidated thermodynamically to show that sequences are able to specifically select their partners. Unlike DNA, the pH dependency of BA/CA binding enables the dehybridization of complementary strands at pH 5.0. In addition, we demonstrate the sequence recognition at the macromolecular level by conjugating the cytochrome c protein to a complementary polyethylene glycol chain in a site-directed fashion.

PENTAFLUOROPHOSPHATE DERIVATIVE, ITS USES AND AN APPROPRIATE MANUFACTURING METHOD

The invention relates to a pentafluorophosphate derivative according to general formula (I): or a pharmaceutically acceptable salt or solvate thereof. Thereby, R1 and R2 denote independently from each other H or F; R3 denotes H, an optionally substituted C1-C10 alkyl, an optionally substituted C3-C10 cycloalkyl, or an optionally substituted C6-C20 aryl, wherein a hydrocarbon chain of the alkyl, the cycloalkyl or the aryl can be interrupted by one or more oxygen, sulfur and/or nitrogen atoms; and M denotes any cation; with the proviso that at least one of R1 and R2 denotes F, if R3 denotes H. The invention further relates to uses of such a pentafluorophosphate derivative and to an appropriate manufacturing method.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Site-Selective Modification of α-Amino Acids and Oligopeptides via Native Amine-Directed γ-C(sp3)-H Arylation

Site-selective modification of chemically and biologically valuable α-amino acids and peptides is of great importance for biochemical study and pharmaceutical development. Few methods based on remote C(sp3)-H functionalization of aliphatic side-chains of peptides has been disclosed in recent years. In this report, we developed a novel approach for γ-C(sp3)-H and γ-/δ-C(sp2)-H arylation of α-amino acids with α-hydrogen by native amine-directed C-H functionalization and further realized the γ-C(sp3)-H arylation of N-terminally unprotected peptides.

Synthesis and Explosion Hazards of 4-Azido- l -phenylalanine

A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-l-phenylalanine beginning from l-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-l-phenylalanine product, however, exhibits previously undocumented explosive characteristics.

A palladium and gold catalytic system enables direct access to O- and S-linked non-natural glyco-conjugates

Here we report a straightforward cross-coupling method for the synthesis of non-natural glycoamino acids from alkyne-bearing monosaccharides and p-iodophenylalanine. Pd/Au-catalyzed Sonogashira coupling is tolerant to both O- and S-glycosides without any epimerization. In addition, no racemization of the amino acid was observed allowing direct access to the homogeneous glyco-conjugate in a single step. Notably, this Pd/Au catalytic system presents enhanced catalytic activity than conventional Pd/Cu and Pd-only platforms, and it further enables the convergent synthesis of glycodipeptides.

Synthesis of six phenylalanine derivatives and their cell toxicity effect on human colon cancer cell line HT-29

Some phenylalanine (Phe) derivatives had important roles in pharmacology and may be used as pharmaceutical materials and pharmaceutical intermediates. In order to understand the cell toxicity of phenylalanine derivatives, we synthesized L-4-bromo-phenylalanine (Brp), L-4-iodophenylalanine (Ip), L-4-nitro-phenylalanine (Np), L-4-sulfonic-phenylalanine (Sp), L-4-phosphophenylalanine (Pp) and L-4-amino-phenylalanine (Np). We used mass spectrometry (MS), Infrared Spectroscopy (IR) or hydrogen-1 nuclear magnetic resonance spectrum (1H-NMR), and high performance liquid chromatography (HPLC) to test the correction of these products, MTT assay and Hoechst 33258 staining to detect their cell toxic effect on human colon cancer cell HT-29 (HT-29 cells). The results showed that these products were correct and the cytotoxicity of Pp>Ip>Sp and Np>Brp, Ap almost had no effect on HT-29 cells. In addition, Pp, Ip and Sp induced cell apoptosis, the other three kinds of phenylalanine derivatives induced neither apoptosis nor necrosis.

PROCESSES AND REAGENTS FOR MAKING DIARYLIODONIUM SALTS

This disclosure relates to processes and reagents for making diaryliodonium salts, which are useful for the preparation of fluorinated, iodinated, astatinated and radiofluorinated aromatic compounds.

Self-liganded Suzuki-Miyaura coupling for site-selective protein PEGylation

Building with PEGs: PEG-boronic acids, in the presence of simple Pd sources, are capable of acting as direct and effective Suzuki reagents in 70-98 % yield. When combined with non-natural amino acids, they allow efficient and direct, site-selective PEGylation of proteins at predetermined positions under biologically compatible conditions without the need for exogenous ligands.