Dde-D-Lys(Fmoc)-OH
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Dde-D-Lys(Fmoc)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-008696
CAS number
1301706-71-7
Molecular Formula
C31H36N2O6
Molecular Weight
532.6
IUPAC Name
(2R)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[1-(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)ethylideneamino]hexanoic acid
Density
1.3±0.1 g/cm3
Boiling Point
740.4±70.0 °C at 760 mmHg
InChI
InChI=1S/C31H36N2O6/c1-19(28-26(34)16-31(2,3)17-27(28)35)33-25(29(36)37)14-8-9-15-32-30(38)39-18-24-22-12-6-4-10-20(22)21-11-5-7-13-23(21)24/h4-7,10-13,24-25,34H,8-9,14-18H2,1-3H3,(H,32,38)(H,36,37)/t25-/m1/s1
InChI Key
HJGADLBSAXYSSH-RUZDIDTESA-N
Canonical SMILES
CC(=NC(CCCCNC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O)C4=C(CC(CC4=O)(C)C)O
1. Method of Glyphosate, AMPA, and Glufosinate Ammonium Determination in Beebread by Liquid Chromatography-Tandem Mass Spectrometry after Molecularly Imprinted Solid-Phase Extraction
Marta Małysiak, Tomasz Kiljanek Molecules. 2022 Sep 5;27(17):5741. doi: 10.3390/molecules27175741.
The aim of this study was to develop a method for the determination of glyphosate, its metabolite aminomethylphosphonic acid (AMPA), and glufosinate ammonium residues in beebread samples, which could then be used to assess bees' exposure to their residues. The complexity of beebread's matrix, combined with the specific properties of glyphosate itself, required careful selection and optimization of each analysis step. The use of molecularly imprinted solid-phase extraction (MIP-SPE) by AFFINIMIP glyphosate as an initial clean-up step significantly eliminated matrix components and ensured an efficient derivatization step. Colorless beebread extracts were derivatized by the addition of 9-fluorenylmethyl chloroformate (FMOC-Cl). After derivatization, in order to remove FMOC-OH and residual borate buffer, a solid-phase extraction (SPE) clean-up step using Oasis HLB was carried out. Instrumental analysis was performed by liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS). The method was validated according to the SANTE/11312/2021 guideline at concentrations of 5, 10, and 100 µg/kg, and satisfactory recovery (trueness) values (76-111%) and precision (RSDr) ≤ 18% were obtained. The limit of quantification (LOQ) was 5 µg/kg for AMPA and glufosinate ammonium and 10 µg/kg for glyphosate. The method was positively verified by the international proficiency test. Analysis of beebread samples showed the method's usefulness in practice. The developed method could be a reliable tool for the assessment of beebread's contamination with residues of glyphosate, its metabolite AMPA, and glufosinate ammonium.
2. Ultratrace-level determination of glyphosate, aminomethylphosphonic acid and glufosinate in natural waters by solid-phase extraction followed by liquid chromatography-tandem mass spectrometry: performance tuning of derivatization, enrichment and detection
Irene Hanke, Heinz Singer, Juliane Hollender Anal Bioanal Chem. 2008 Jul;391(6):2265-76. doi: 10.1007/s00216-008-2134-5. Epub 2008 May 16.
A sensitive and robust analytical method for the quantification of glyphosate, aminomethylphosphonic acid (AMPA) and glufosinate in natural water has been developed on the basis of a derivatization with 9-fluorenylmethylchloroformate (FMOC-Cl), solid-phase extraction (SPE) and liquid chromatography followed by electrospray tandem mass spectrometry (LC-ESI-MS/MS). In order to maximize sensitivity, the derivatization was optimized regarding organic solvent content, amount of FMOC-Cl and reaction time. At an acetonitrile content of 10% a derivatization yield of 100% was reached within two hours in groundwater and surface water samples. After a twofold dilution the low acetonitrile content allowed solid-phase extraction of a sample of originally 80 mL over 200 mg Strata-X cartridges. In order to decrease the load of the LC column and mass spectrometer with derivatization by-products (e.g., 9-fluorenylmethanol FMOC-OH), a rinsing step was performed for the SPE cartridge with dichloromethane. Acidification of the sample and addition of EDTA was used to minimize complexation of the target compounds with metal ions in environmental samples. Due to the large sample volume and the complete FMOC-OH removal, limits of quantification of 0.7 ng/L, 0.8 ng/L and 2.3 ng/L were achieved in surface water for glyphosate, AMPA and glufosinate, respectively. The limits of detection were as low as 0.2 ng/L, 0.2 ng/L and 0.6 ng/L for glyphosate, AMPA and glufosinate, respectively. Surface water and ground water samples spiked at 2 ng/L showed recoveries of 91-107%.
3. A novel fluorescent chemosensor for detection of mercury(II) ions based on dansyl-peptide and its application in real water samples and living LNcap cells
Shirui Xue, Peng Wang, Kai Chen Spectrochim Acta A Mol Biomol Spectrosc. 2020 Feb 5;226:117616. doi: 10.1016/j.saa.2019.117616. Epub 2019 Oct 7.
Mercury is one of the most hazardous pollutants, and mercury pollution is a serious hazard to our environment. Herein, we designed and synthesized a new peptide-based fluorescent chemosensor (L) based on a Fmoc-Lys (Fmoc)-OH backbone conjugated with two Serines and dansyl groups using solid phase peptide synthesis (SPPS) technology. L exhibited highly selective and excellent sensitive detection of Hg2+ ions in 100% aqueous solutions through fluorescence quenching. The chemosensor L forms a 2:1 stoichiometry with high binding constants (4.89×106M-1) and the detection limit for Hg2+ ions of the proposed assay was 7.59nM. In addition, the recovery test results of Hg2+ concentration in actual water samples showed that the quantitative detection of Hg2+ ions can be realized in two water samples. Moreover, L showed low cytotoxicity and excellent membrane permeability in HK2 cells, which has been successfully applied for monitoring Hg2+ ions in living LNCaP cells.
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