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Chemistry
Organic Building Blocks
Fluorinated Building Blocks
(R)-2-((5-Fluoro-2,4-dinitrophenyl)amino)propanamide
Chemistry
Life Science
Organic Building Blocks
Amino Acids
Fluorinated Building Blocks
Nitroes Amino Acid Derivatives Benzene Compounds

[ CAS No. 132055-99-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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3d Animation Molecule Structure of 132055-99-3
Chemical Structure| 132055-99-3
Chemical Structure| 132055-99-3
Structure of 132055-99-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 132055-99-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 132055-99-3 ]

Product Details of [ 132055-99-3 ]

CAS No. :132055-99-3 MDL No. :MFCD00155642
Formula : C9H9FN4O5 Boiling Point : -
Linear Structure Formula :- InChI Key :NEPLBHLFDJOJGP-SCSAIBSYSA-N
M.W : 272.19 Pubchem ID :125721
Synonyms :

Safety of [ 132055-99-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 132055-99-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 132055-99-3 ]

[ 132055-99-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 73-32-5 ]
  • Nα-(2,4-dinitro-5-fluorophenyl)-D-alaninamide [ No CAS ]
  • D-FDAA-L-Ile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In water at 40℃; for 0.75h;
With sodium hydrogencarbonate In water at 40℃; for 0.75h; 4.5. Advanced Marfey's analysis of amino acid residues in 1 General procedure: For the analysis of the Ile unit in 1, additional lagunamide C (0.5 mg) was hydrolyzed in 6 N HCl at 110 °C for 20 h and was derivatized with Marfey's reagent (L-FDAA) as described above. Two portions each of 0.5 mg standard L-Ile and L-allo-Ile were dissolved in 100 μL of H2O. A 1.0% solution of L-FDAA (100 μL) and 1 N NaHCO3 (20 μL) were added to one portion each of L-Ile and L-allo- Ile and to the other portions were added 1.0% solution of D-FDAA (100 μL) and 1 N NaHCO3 (20 μL). All four mixtures were then heated at 40 °C for 45 min. The solution were cooled to r.t., neutralized with 2 N HCl (10 μL) and evaporated to dryness. The residues were then resuspended in MeCN (500 μL). The aliquots were subjected to reversed-phase LC-MS (Agilent 1100 series) accordingto the Marfey's method [column: Phenomenex, Luna, 150 x 2.0 mm, 5 μm, 100 Å; mobile phase, MeCN in 0.1% (v/v) aqueous HCOOH; flow rate, 0.20 mL/min] using a linear gradient (30-70% MeCN over 40 min) (Marfey, 1984; Fuji et al., 1997a,b). An Agilent 1100 series MSD spectrometer was used for detection in API-ES(negative mode). The derivatized Ile residue in the hydrolysate of 1 eluted at the same retention time as the derivatized standard L-allo-Ile (14.2 min) but not that of L-Ile (13.0 min), D-Ile (=D-FDAA derivatized L-Ile , 17.3 min) and D-allo-Ile (=D-FDAA derivatized L-allo-Ile, 17.8 min).
With sodium hydrogencarbonate In water; acetone at 40℃; for 1h;
With triethylamine In acetone; acetonitrile at 50℃; for 1.5h;
With sodium hydrogencarbonate In acetone at 50℃; for 1h; Marfey analysis General procedure: The absolute configurations of the amino acids present in1 and 2 were determined by the Marfey’s method [15, 16].Briefly, solutions at 50 μM of each L-amino acid (proline,leucine, isoleucine and phenylalanine) were prepared. Then,50 μl of each solution was treated with a 1-fluoro-2,4-dinitrophenyl-5-L-alaninamide (L-FDAA) at 1% in acetone(100 μl) and sodium bicarbonate 1M (20 μl). The mixturewas heated for 1 h at 50 °C. Subsequently, the mixture wascooled to room temperature, and a solution of HCl 1M(10 μl) was added. The obtained residue was dried in adesiccator over NaOH pellets and dissolved in DMSO(1 ml). The same procedure was repeated employing1-fluoro-2,4-dinitrophenyl-5-D-alaninamide (D-FDAA).HPLC analyses were performed in a HPLC-DAD (agilent1260), symmetry C-18 column (100 × 4.6 mm, 3.5 μm)eluting with a first step gradient (MeCN-HCOOH 0,1%)from 10:90 up to 18:82 in 30 min, followed by a secondgradient from 18:82 up to 40:60 in 15 min, and maintaining40:40 for other 10 min for a total run time of 55 min, at aflow rate of 2 ml min-1 and 25 °C, and detecting on a DADdetector.

Reference： [1]Location in patent: experimental part Tripathi, Ashootosh; Puddick, Jonathan; Prinsep, Michele R.; Rottmann, Matthias; Tan, Lik Tong [Journal of Natural Products, 2010, vol. 73, # 11, p. 1810 - 1814]
[2]Location in patent: experimental part Tripathi, Ashootosh; Puddick, Jonathan; Prinsep, Michele R.; Rottmann, Matthias; Chan, Kok Ping; Chen, David Yu-Kai; Tan, Lik Tong [Phytochemistry, 2011, vol. 72, # 18, p. 2369 - 2375]
[3]Vijayasarathy, Soumini; Prasad, Pritesh; Fremlin, Leith J.; Ratnayake, Ranjala; Salim, Angela A.; Khalil, Zeinab; Capon, Robert J. [Journal of Natural Products, 2016, vol. 79, # 2, p. 421 - 427]
[4]Teta, Roberta; Marteinsson, Viggó Thór; Longeon, Arlette; Klonowski, Alexandra M.; Groben, René; Bourguet-Kondracki, Marie-Lise; Costantino, Valeria; Mangoni, Alfonso [Journal of Natural Products, 2017, vol. 80, # 9, p. 2530 - 2535]
[5]Betancur, Luz A.; Forero, Abel M.; Romero-Otero, Adriana; Sepúlveda, Lady Yohanna; Moreno-Sarmiento, Nubia C.; Castellanos, Leonardo; Ramos, Freddy A. [Journal of Antibiotics, 2019, vol. 72, # 10, p. 744 - 751]
  • 2
  • [ 72-18-4 ]
  • Nα-(2,4-dinitro-5-fluorophenyl)-D-alaninamide [ No CAS ]
  • L-valine-D-FDAA [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In water; acetone at 80℃; for 0.166667h;
With triethylamine In acetone; acetonitrile at 50℃; for 1h; 4.3.2. Marfey’s Derivatization with D- and L-FDAA General procedure: The hydrolysate of 3 was dissolved in triethylamine/ACN (2:3) (80 μL), and this solution was then treated with 1% 1-fluoro-2,4-dinitrophenyl-5-L-alaninamide (L-FDAA) in ACN/acetone (1:2) (75 μL). The vial was heated at 50 °C for 1 h. The mixture was dried and resuspended in ACN/H2O (5:95) (500 μL) for subsequent LC-MS analysis (I). The hydrolysate of 4 was treated with D-FDAA under identical conditions as 3 (II). Authentic L-Val and L-Pro standards were treated with L-FDAA and D-FDAA as above (III).
With sodium hydrogencarbonate In water; acetone at 40℃; for 1h;
With triethylamine In acetone; acetonitrile at 50℃; for 1.5h;
With sodium hydrogencarbonate In acetone at 40℃; for 1h;

Reference： [1]Um, Soohyun; Park, So Hyun; Kim, Jihye; Park, Hyen Joo; Ko, Keebeom; Bang, Hea-Son; Lee, Sang Kook; Shin, Jongheon; Oh, Dong-Chan [Organic Letters, 2015, vol. 17, # 5, p. 1272 - 1275]
[2]Esposito, Germana; Teta, Roberta; Miceli, Roberta; Ceccarelli, Luca S.; Sala, Gerardo Della; Camerlingo, Rosa; Irollo, Elena; Mangoni, Alfonso; Pirozzi, Giuseppe; Costantino, Valeria [Marine Drugs, 2015, vol. 13, # 1, p. 444 - 459]
[3]Vijayasarathy, Soumini; Prasad, Pritesh; Fremlin, Leith J.; Ratnayake, Ranjala; Salim, Angela A.; Khalil, Zeinab; Capon, Robert J. [Journal of Natural Products, 2016, vol. 79, # 2, p. 421 - 427]
[4]Teta, Roberta; Marteinsson, Viggó Thór; Longeon, Arlette; Klonowski, Alexandra M.; Groben, René; Bourguet-Kondracki, Marie-Lise; Costantino, Valeria; Mangoni, Alfonso [Journal of Natural Products, 2017, vol. 80, # 9, p. 2530 - 2535]
[5]Cottrell, Garrison W.; Fang, Fang; Gerwick, Lena; Gerwick, William H.; Glukhov, Evgenia; Guan, Huashi; Kim, Hyunwoo; Leao, Tiago; Li, Yueying; Mao, Huanru Henry; Murray, Thomas F.; Pierce, Marsha L.; Yu, Hao-Bing; Zhang, Chen; Zhang, Yi [Journal of Natural Products, 2020]

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[ 132055-99-3 ]

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[ 95713-52-3 ]

(S)-2-((5-Fluoro-2,4-dinitrophenyl)amino)propanamide

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