Fmoc-Cl

solid phase peptide synthesis CAS# 28920-43-6

Fmoc-Cl

Catalog No. BCC2802----Order now to get a substantial discount!

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Quality Control of Fmoc-Cl

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Chemical structure

Fmoc-Cl

3D structure

Chemical Properties of Fmoc-Cl

Cas No. 28920-43-6 SDF Download SDF
PubChem ID 34367 Appearance Powder
Formula C15H11ClO2 M.Wt 258.7
Type of Compound N/A Storage Desiccate at -20°C
Solubility >25.9mg/ml in DMSO
Chemical Name 9H-fluoren-9-ylmethyl carbonochloridate
SMILES C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)Cl
Standard InChIKey IRXSLJNXXZKURP-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Fmoc-Cl Dilution Calculator

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Fmoc-Cl Molarity Calculator

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Preparing Stock Solutions of Fmoc-Cl

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.8655 mL 19.3274 mL 38.6548 mL 77.3096 mL 96.637 mL
5 mM 0.7731 mL 3.8655 mL 7.731 mL 15.4619 mL 19.3274 mL
10 mM 0.3865 mL 1.9327 mL 3.8655 mL 7.731 mL 9.6637 mL
50 mM 0.0773 mL 0.3865 mL 0.7731 mL 1.5462 mL 1.9327 mL
100 mM 0.0387 mL 0.1933 mL 0.3865 mL 0.7731 mL 0.9664 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Fmoc-Cl

IC50: A series of Fmoc-based dipeptides were reported to show cytotoxicity in human cancer cell lines with the IC50 ranges from 0.4 to 1.0 M.

Fmoc-Cl, a chloroformate ester, is commonly applied to introduce Fmoc group during the formation of Fmoc carbamate. Fmoc-based dipeptides are widely explored as a potential anticancer drug. Fmoc protection also serves as a crucial method in solid phase peptide synthesis because it could be removed by piperidine without disturbing the linker between the peptide and the resin. In addition, due to the fluorescent property of Fmoc group, it could react with certain UV-undetectable compounds to form Fmoc derivatives which are feasible for HPLC analysis. [1]

In vitro: Among thirty studied Fmoc-based dipeptides, there were nine compounds intensively against tumor cell growth in human cancer cell lines including HepG2, Hep3B, MCF-7, MDA-MB-231, A549 and Ca9-22. The most active Fmoc-based dipeptide exhibited the highest sensitivity in Ca9-22 cell lines with an IC50 of 0.4 μM, which was 3-fold more potent than doxorubicin. Moreover, this compound had synergistic effect to enhance the antitumor activity of doxorubicin. [1]

In vivo: Peptide derived from Fmoc solid-phase synthesis was reported to have antiestrogenic and anticancer activities. Specifically, intraperitoneal administration of 0.5 μg such peptide had shown to prevent carcinogen-induced mammary cancer in rats and suppress the growth of ER+ human breast cancer xenografts in mice. [2]

Clinical trial: So far, no clinical trial has been conducted.

References:
[1] Yena CT, Wua CC, Leed JC, Chena SL, Morris-Natschkec SL, Hsiehb PW, Wua YC.  Cytotoxic N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides: Structure–activity relationships and synergistic studies. Eur J Med Chem. 2010 Jun; 45(6): 2494-502.
[2] Joseph LC, Bennett JA, Kirschner KN, Shields GC, Hughes J, Lostritto N, Jacobsona H, Andersen TT.  Antiestrogenic and anticancer activities of peptides derived from the active site of alpha-fetoprotein. J Pept Sci. 2009 Feb; 15: 319–25.

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References on Fmoc-Cl

Applicability of LC-MS/MS to optimize derivatization of topiramate with FMOC-Cl using reacted/intact drug ratio.[Pubmed:23598049]

J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Jun 1;928:32-6.

Topiramate is an antiepileptic agent, which is structurally different from the other anticonvulsants. The drug has no UV-Vis absorption or emits fluorescence. Thus for its analysis using high performance liquid chromatography (HPLC) with conventional UV or fluorescence detectors, the drug should be derivatized with a suitable reagent. In previous study using fluorenylmethyl chloroformate (Fmoc-Cl) and HPLC coupled with fluorescence detector, we reported an analytical method for derivatization and analysis of the drug in human serum. In this method, several factors including time and temperature of the reaction, pH and concentration of the used buffer, ratio of organic phase in the medium and removal of the reagent excess by glycine should be optimized to obtain maximum yield of the product. In HPLC coupled with fluorescence detector, there is not any signal from intact topiramate and only the final product (FMOC-topiramate) is appeared. Thus to optimize the reaction conditions for obtaining the highest derived yield, intensity of the final product peak is considered as a criteria for progression of the reaction. In LC-MS/MS system however, both free and reacted topiramate are visible in observed spectra. In the present study reaction of the drug with Fmoc-Cl was re-optimized using LC-MS/MS technique on the basis of reacted/free topiramate ratio as the new and more accurate index. The results showed that, ratio of organic/aqueous phase has a dominant effect on the reaction, the most efficient temperature is 70 degrees C and the reaction is reversed following addition of the glycine.

Analysis of amino acids by HPLC/electrospray negative ion tandem mass spectrometry using 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) derivatization.[Pubmed:25218137]

Amino Acids. 2014 Dec;46(12):2799-808.

A new method for the determination of amino acids is presented. It combines established methods for the derivatization of primary and secondary amino groups with 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) with the subsequent amino acid specific detection of the derivatives by LC-ESI-MS/MS using multiple reaction monitoring (MRM). The derivatization proceeds within 5 min, and the resulting amino acid derivatives can be rapidly purified from matrix by solid-phase extraction (SPE) on HR-X resin and separated by reversed-phase HPLC. The Fmoc derivatives yield several amino acid specific fragment ions which opened the possibility to select amino acid specific MRM transitions. The method was applied to all 20 proteinogenic amino acids, and the quantification was performed using L-norvaline as standard. A limit of detection as low as 1 fmol/microl with a linear range of up to 125 pmol/microl could be obtained. Intraday and interday precisions were lower than 10 % relative standard deviations for most of the amino acids. Quantification using L-norvaline as internal standard gave very similar results compared to the quantification using deuterated amino acid as internal standards. Using this protocol, it was possible to record the amino acid profiles of only a single root from Arabidopsis thaliana seedlings and to compare it with the amino acid profiles of 20 dissected root meristems (200 mum).

Fmoc-Cl fluorescent determination for amino groups of nanomaterial science.[Pubmed:22559711]

IET Nanobiotechnol. 2012 Jun;6(2):76-80.

With the wide application of nanomaterials, the quantification of functional groups on nanomaterial surface becomes more and more necessary. A heterogeneous 9-fluorenylmethoxy carbonyl chloride (Fmoc-Cl) fluorescent method using an aqueous solution was established to determinate amino groups on nanomaterial surface. The effect factors of determination were investigated and the assay was optimised. The Fmoc fluorescent method is 200-fold more sensitive than the current UV assay using an organic solvent, and compared with chemical ninhydrin method and physical elemental analysis. Heterogeneous Fmoc-Cl fluorescent method can be used to determine amino groups on nanomaterials with big size, which is difficult to undergo a direct detection.

Determination of biogenic amines in infusions of tea (Camellia sinensis) by HPLC after derivatization with 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl).[Pubmed:21800261]

Amino Acids. 2012 Feb;42(2-3):877-85.

The reagent 9-fluorenylmethoxycarbonyl chloride (Fmoc-Cl) was used for the pre-column derivatization of the biogenic amines (BAs) cadaverine (Cad), histamine (Him), octopamine (Ocp), phenylethylamine (Pea), putrescine (Put), spermidine (Spd), spermine (Spm), tyramine (Tym) and the internal standard 1,6-diaminohexane (Dhx). The resulting Fmoc-derivatives were resolved by high-performance liquid chromatography on a Superspher((c)) C(18) column using a binary gradient generated from sodium acetate and acetonitrile. For quantification, the fluorescence of derivatives was used at 263 nm excitation and 313 nm emission wavelength. This approach was applied to free BAs extractable with boiling water from 14 black, 5 green, 1 Oolong, and 1 instant tea. Infusions were prepared by adding 35 ml boiling water to one gram of tea and extracted for 20 min. In the Oolong tea and two black teas, no BAs could be detected. Limits of detection were 0.07-1.0 pmol for BAs at signal-to-noise ratio 3:1. Besides most abundant Tym and Spm lower quantities of Pea, Put, and Spd were detected, albeit not in all teas. Quantities of Tym ranged from 16 to 431 mug Tym/L infusion (1.1-25.3 mug Tym/g tea) and 31 to 319 mug Spm/L infusion (1.5-16.9 mug Spm/g tea). In none of the teas, Him was detected. Owing to the low amounts of free BAs in tea infusions, no health risks are to be expected even on consumption of large quantities of tea as beverage.

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