112883-40-6

Basic information

• Product Name: Fmoc-Met-OH
• Synonyms: FMOC-D-MET-OH;FMOC-D-METHIONINE;FMOC-D-MET;9-FLUORENYLMETHOXYCARBONYL-D-METHIONINE;N-FMOC-D-METHIONINE;N-ALPHA-FMOC-D-METHIONINE;N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-METHIONINE;N-9-FLUORENYLMETHYLOXYCARBONYL-D-METHIONINE
• CAS NO: 112883-40-6
• Molecular Formula: C₂₀H₂₁NO₄S
• Molecular Weight: 371.45
• EINECS: 276-258-5
• Product Categories: Amino Acids;Methionine [Met, M];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 112883-40-6.mol

Chemical Properties

• Melting Point: 132 °C
• Boiling Point: 614.6 °C at 760 mmHg
• Flash Point: 325.5 °C
• Appearance: /
• Density: 1.282 g/cm³
• Vapor Pressure: 5.8E-16mmHg at 25°C
• Refractive Index: 30 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMF (Slightly), Methanol (Slightly)
• PKA: 3.72±0.10(Predicted)
• BRN: 5384578
• CAS DataBase Reference: Fmoc-Met-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-Met-OH(112883-40-6)
• EPA Substance Registry System: Fmoc-Met-OH(112883-40-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 112883-40-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-Met-OH is used as a cytoprotectant for its ability to protect cells against the harmful effects of Cisplatin, an anticancer agent. It is particularly effective in preventing noiseand drug-induced hearing loss, as well as hair loss, which may be caused by Cisplatin or aminoglycosides.
Used in Research and Development:
Fmoc-Met-OH is used as a research compound for studying the effects of D-Methionine and its potential applications in various fields, including pharmaceuticals, biotechnology, and chemical synthesis.
Used in Chemical Synthesis:
Fmoc-Met-OH is used as a protected amino acid in the synthesis of peptides and other biomolecules, where the Fmoc group provides protection during the synthesis process and can be removed when needed to reveal the free amino acid.

InChI:InChI=1/C20H21NO4S/c1-26-11-10-18(19(22)23)21-20(24)25-12-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,10-12H2,1H3,(H,21,24)(H,22,23)/t18-/m1/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 144701-23-5 N-Fmoc-methionine 
• 59-51-8 DL-methionine 

Downstream Products

• 1213773-72-8 O-W-F-I-M-H(1-Bzl)-NH₂ 
• 1213773-08-0 O-W-M-I-F-H(1-Bzl)-NH₂ 
• 1213773-41-1 O-W-F-M-F-H(1-Bzl)-NH₂ 
• 1374451-21-4 C₅₁H₅₄Cl₃N₃O₇S₂ 
• 187986-11-4 W peptide 
• 187986-11-4 wkymvm-NH₂ 

Relevant articles and documents

Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety

Novel chiral selectors based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin connecting quinine (QN) or quinidine (QD) moiety were synthesized and immobilized on silica gel. Their chromatographic performances were investigated by comparing to the 3,5-dimethyl phenylcarbamoylated β-cyclodextrin (β-CD) chiral stationary phase (CSP) and 9-O-(tert-butylcarbamoyl)-QN-based CSP (QN-AX). Fmoc-protected amino acids, chiral drug cloprostenol (which has been successfully employed in veterinary medicine), and neutral chiral analytes were evaluated on CSPs, and the results showed that the novel CSPs characterized as both enantioseparation capabilities of CD-based CSP and QN/QD-based CSPs have broader application range than β-CD-based CSP or QN/QD-based CSPs. It was found that QN/QD moieties play a dominant role in the overall enantioseparation process of Fmoc-amino acids accompanied by the synergistic effect of β-CD moiety, which lead to the different enantioseparation of β-CD-QN-based CSP and β-CD-QD-based CSP. Furthermore, new CSPs retain extraordinary enantioseparation of cyclodextrin-based CSP for some neutral analytes on normal phase and even exhibit better enantioseparation than the corresponding β-CD-based CSP for certain samples.

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.