35661-40-6

Basic information

• Product Name: FMOC-L-Phenylalanine
• Synonyms: FMOC-L-PHE;FMOC-L-PHENYLALANINE;FMOC-L-PHE-OH;9-FLUORENYLMETHOXYCARBONYL-L-PHENYLALANINE;N-(9-FLUORENYLMETHOXYCARBONYL)-L-PHENYLALANINE;N-9-FLUORENYLMETHYLOXYCARBONYL-L-PHENYLALANINE;N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-L-PHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-PHENYLALANINE
• CAS NO: 35661-40-6
• Molecular Formula: C₂₄H₂₁NO₄
• Molecular Weight: 387.43
• EINECS: 252-661-1
• Product Categories: Protected Amino Acids;Fluorenes, Flurenones;Amino Acids;Phenylalanine [Phe, F];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series;A;Benzopyrans
• Mol File: 35661-40-6.mol
• Article Data: 57

Chemical Properties

• Melting Point: 180-187 °C(lit.)
• Boiling Point: 513.39°C (rough estimate)
• Flash Point: 328.8 °C
• Appearance: White/Powder
• Density: 1.2379 (rough estimate)
• Vapor Pressure: 3.07E-16mmHg at 25°C
• Refractive Index: -39.5 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMF (Sparingly, Sonicated), DMSO (Slightly)
• PKA: 3.77±0.10(Predicted)
• BRN: 3597808
• CAS DataBase Reference: FMOC-L-Phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-Phenylalanine(35661-40-6)
• EPA Substance Registry System: FMOC-L-Phenylalanine(35661-40-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26
• WGK Germany: 3
• Hazardous Substances Data: 35661-40-6(Hazardous Substances Data)

Usage

Description

FMOC-L-Phenylalanine, also known as Fmoc-Phe-OH, is a derivative of L-Phenylalanine, an essential amino acid. It is a white to light yellow crystalline powder and is commonly used in the synthesis of peptides and deltorphin derivatives. FMOC-L-Phenylalanine has potential applications as an inhibitor of the IGF-I and IGF-Binding Protein-5 complex, which may have implications in various biological and medical research areas.

Uses

Used in Pharmaceutical Industry:
FMOC-L-Phenylalanine is used as a building block for the synthesis of peptides and peptide-based drugs. Its incorporation into peptide structures allows for the development of novel therapeutic agents with specific biological activities.
Used in Research and Development:
FMOC-L-Phenylalanine serves as a valuable tool in the research and development of new drugs and therapies. It is used in the preparation of deltorphin derivatives, which are known for their potent analgesic properties. This amino acid derivative can also be utilized in the study of the IGF-I and IGF-Binding Protein-5 complex, potentially leading to the development of treatments for conditions related to these proteins.
Used in Chemical Synthesis:
As a chemical intermediate, FMOC-L-Phenylalanine is used in the synthesis of various compounds with specific functional groups. Its reactivity and structural properties make it a versatile building block for creating complex molecules with tailored properties for different applications.

InChI:InChI=1/C24H21NO4/c26-23(27)22(14-16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)(H,26,27)/p-1/t22-/m0/s1

Upstream product

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• 100821-63-4 1,2,2,2-Tetrachloroethyl 9-fluorenylmethyl carbonate 
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• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 99503-04-5 Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 150-30-1 Phenylalanine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 21715-90-2 N-hydroxy-5-norbornene-2,3-dicarboximide 
• 127556-05-2 (2R)-N-<(2S)-2-<amino>-3-phenylpropan-1-oyl>bornane-10,2-sultam 
• 168958-30-3 (S)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-phenyl-propan-1-one 
• 5269-44-3 O-(Trimethylsilyl)phenylalanine 
• 246158-11-2 tert-butyl [(1S,2S)-2-azido-3-(4-tert-butoxyphenyl)-1-(2-oxoethyl)propoxy]acetate 

Downstream Products

• 146803-37-4 N-(fluorenylmethyloxycarbonyl)-L-phenylalanine S-benzyl thioester 
• 58822-25-6 Leu-enkephalin 

Relevant articles and documents

A combined SPS-LCD sensor for screening protease specificity

A hydrogel-based sensor for screening protease specificity has been developed that combines the versatility of solid-phase synthesis (SPS) with the simplicity of liquid crystal display (LCD) technology. The Royal Society of Chemistry.

Single Amino-Acid Based Self-Assembled Biomaterials with Potent Antimicrobial Activity

The design and development of soft biomaterials based on amino acid and short-peptide have gained much attention due to their potent biomedical applications. A slight alteration in the side-chain of single amino acid in a peptide or protein sequence has a huge impact on the structure and function. Phenylalanine is one of the most studied amino acids, which contains an aromatic phenyl group connected through a flexible ?CH2? unit. In this work, we have examined whether flexibility and aromatic functionality of phenylalanine (Phe) are important in gel formation of model gelator Fmoc-Phe-OH or not. To examine this hypothesis, we synthesized Fmoc-derivatives of three analogues unnatural amino acids including cyclohexylalanine, phenylglycine, and homophenylalanine; which are slightly varied from Phe. Interestingly, all these three new analogues formed hydrogels in phosphate buffer at pH 7.0 having different gelation efficacy and kinetics. This study suggests that the presence of aromatic side-chain and flexibility are not mandatory for the gelation of this model gelator. Newly synthesized unnatural amino acid derivatives have also exhibited promising antimicrobial activity towards gram-positive bacteria by inhibiting cellular oxygen consumption. We further determined the biocompatibility of these amino acid derivatives by using a hemolysis assay on human blood cells. Overall studies described the development of single amino acid-based new injectable biomaterials with improved antimicrobial activity by the slight alteration in the side-chain of amino acid.

Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases

Liquid chromatographic enantiomer separation and simultaneous determination of chemical and enantiomeric purity of α-amino acids and their methyl esters as N-fluorenylmethoxycarbonyl (FMOC) derivatives was performed on three covalently bonded type chiral stationary phases (CSPs) derived from amylose derivatives. The enantiomer separation of α-amino acid esters as N-FMOC derivatives was better than that of the corresponding acids, especially for CSP 1 and 2. Chemical impurities as the corresponding racemic acids present in several commercially available racemic amino acid methyl esters were observed to be 0.49–17.50%. Enantiomeric impurities of several commercially available L-amino acid methyl esters were found to be 0.03–0.58%, whereas chemical impurities as the corresponding racemic acids present in the same analytes were found to be 0.13–13.62%. This developed analytical method will be useful for the determination of chemical and enantiomeric purity of α-amino acids and/or esters as N-FMOC derivatives using amylose-derived CSPs.