103321-57-9

Basic information

• Product Name: FMOC-L-PHENYLALANYL CHLORIDE
• Synonyms: FMOC-PHE-CL;FMOC-L-PHENYLALANYL CHLORIDE;NALPHA-9-Fluorenylmethoxycarbonyl-L-phenylalanyl chloride;N-(9-Fluorenylmethoxycarbonyl)phenylalanyl chloride;N-[(1S)-2-Chloro-2-oxo-1-(phenylmethyl)ethyl]carbamic acid 9H-fluoren-9-ylmethyl ester;(S)-(9H-Fluoren-9-yl)methyl (1-chloro-1-oxo-3-phenylpropan-2-yl)carbamate;Carbamic acid, N-[(1S)-2-chloro-2-oxo-1-(phenylmethyl)ethyl]-, 9H-fluoren-9-ylmethyl ester
• CAS NO: 103321-57-9
• Molecular Formula: C₂₄H₂₀ClNO₃
• Molecular Weight: 405.87
• Product Categories: Amino Acids
• Mol File: 103321-57-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: 116-118℃
• Boiling Point: 596.205 °C at 760 mmHg
• Flash Point: 314.374 °C
• Appearance: /
• Density: 1.279
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: FMOC-L-PHENYLALANYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-PHENYLALANYL CHLORIDE(103321-57-9)
• EPA Substance Registry System: FMOC-L-PHENYLALANYL CHLORIDE(103321-57-9)

Safety Data

• Hazardous Substances Data: 103321-57-9(Hazardous Substances Data)

Usage

Description

FMOC-L-PHENYLALANYL CHLORIDE, also known as Fmoc-L-Phe-Cl, is a chemical compound that serves as an amino acid derivative in peptide synthesis. It is characterized by the presence of a chlorine atom and the FMOC (9-fluorenylmethyloxycarbonyl) group, which acts as a protective group for the amino acid during synthesis, preventing unwanted side reactions. FMOC-L-PHENYLALANYL CHLORIDE is primarily used in laboratory settings, specifically in biochemical and pharmaceutical research, due to its fundamental role in creating complex proteins and peptides. The use of FMOC-L-PHENYLALANYL CHLORIDE requires specialized knowledge and care due to its potential reactivity.

Uses

Used in Biochemical Research:
FMOC-L-PHENYLALANYL CHLORIDE is used as a building block for the synthesis of peptides and proteins, allowing researchers to construct complex biological molecules with specific functions and properties. The FMOC group provides protection to the amino acid, ensuring that the desired peptide sequence is formed without interference from side reactions.
Used in Pharmaceutical Research:
FMOC-L-PHENYLALANYL CHLORIDE is used as a key component in the development of new drugs and therapeutic agents. Its role in peptide synthesis enables the creation of novel compounds with potential medicinal applications, such as antibiotics, vaccines, and other bioactive molecules. The protective nature of the FMOC group ensures that the synthesized peptides maintain their intended structure and activity, which is crucial for their effectiveness as pharmaceutical agents.
Used in Laboratory Settings:
FMOC-L-PHENYLALANYL CHLORIDE is used as a reagent in various laboratory procedures, such as solid-phase peptide synthesis and liquid-phase peptide synthesis. Its presence allows for the stepwise assembly of peptides and proteins, with the FMOC group being removed at each step to reveal the newly formed amino acid. This methodical approach ensures precise control over the synthesis process, leading to the production of high-quality peptides and proteins for research purposes.

InChI:InChI=1/C24H20ClNO3/c25-23(27)22(14-16-8-2-1-3-9-16)26-24(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,26,28)/t22-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 63-91-2 L-phenylalanine 
• 35661-40-6 N-Fmoc L-Phe 

Downstream Products

• 112667-29-5 N-(9-fluorenylmethoxycarbonyl)-L-phenylalaninamide 
• 193954-28-8 (S)-3-(9H-fluoren-9-yl)methoxycarbonylamino-4-phenylbutanoic acid 
• 611198-23-3 Fmoc-Phe-NCO 
• 252032-23-8 (1R,4S)-1,3,4,6-tetrahydro-3,6-dioxo-1-(phenylmethyl)-2H-pyrazino[2,1-b]quinazoline-4-propanamide 
• 252032-22-7 (1S,4S)-1,3,4,6-tetrahydro-3,6-dioxo-1-(phenylmethyl)-2H-pyrazino[2,1-b]quinazoline-4-propanamide 

Relevant articles and documents

Bioinspired honokiol analogs and their evaluation for activity on the norepinephrine transporter

In traditional Asian medicinal systems, preparations of the root and stem bark of Magnolia species are widely used to treat anxiety and other nervous disturbances. The biphenyl-type neolignans honokiol and magnolol are the main constituents of Magnolia bark extracts. In the central nervous system, Magnolia bark preparations that contain honokiol are thought to primarily interact with -aminobutyric acid A (GABAA) receptors. However, stress responses inherently involve the noradrenergic system, which has not been investigated in the pharmacological mechanism of honokiol. We present here interactions of honokiol and other synthesized biphenyl-type neolignans and diphenylmethane analogs with the norepinephrine transporter (NET), which is responsible for the synaptic clearance of norepinephrine and the target of many anxiolytics. Of the synthesized compounds, 16 are new chemical entities, which are fully characterized. The 52 compounds tested show mild, non-potent interactions with NET (IC50 > 100 μM). It is thus likely that the observed anxiolytic effects of, e.g., Magnolia preparations, are not due to direct interaction with the noradrenergic system.

Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry

The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline is reported. The key steps are a Ruppert-Prakash reagent addition on l-pyroglutamic esters followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.

One-pot synthesis of Weinreb amides employing 3,3-dichloro-1,2-diphenylcyclopropene (CPI-Cl) as a chlorinating agent

The synthesis of Nα-protected amino alkyl Weinreb amides starting from the corresponding α-amino acids as well as carboxylic acids has been delineated through the in situ generation of acid chlorides using CPI-Cl as a chlorinating agent. The protocol is simple; the reaction conditions employed were mild, and compatible with all the three commonly used urethane protecting groups namely, Boc, Cbz and Fmoc groups. The resulting Weinreb amides are obtained in good yields as optically pure products.