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Fmoc-4-nitro-L-phenylalanine

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Fmoc-4-nitro-L-phenylalanine manufacturers

  • Fmoc-Phe(4-NO2)-OH
  • Fmoc-Phe(4-NO2)-OH pictures
  • $1.00
  • 2020-01-06
  • CAS:95753-55-2
  • Min. Order: 1g
  • Purity: 98%
  • Supply Ability: 100KG
Fmoc-4-nitro-L-phenylalanine Basic information
Product Name:Fmoc-4-nitro-L-phenylalanine
Synonyms:Fmoc-Phe(4-NO2)-OH;9-FLUORENYLMETHOXYCARBONYL-P-NITRO-L-PHENYLALANINE;4-Nitro-L-phenylalanine, N-FMOC protected;Fmoc-L-4-NO2-Phe-OH;NALPHA-9-Fluorenylmethoxycarbonyl-3-(4-nitrophenyl)-L-alanine;N-(9-Fluorenylmethyloxycarbonyl)-L-4-nitrophenylalanine;FMOC-4-NITRO PHENYLALANINE;FMOC-4-NITRO-PHE-OH
CAS:95753-55-2
MF:C24H20N2O6
MW:432.43
EINECS:
Product Categories:Phenylalanine [Phe, F];Unusual Amino Acids;Fmoc-Amino acid series;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acids
Mol File:95753-55-2.mol
Fmoc-4-nitro-L-phenylalanine Structure
Fmoc-4-nitro-L-phenylalanine Chemical Properties
Melting point 213-223℃
Boiling point 692.3±55.0 °C(Predicted)
density 1.371±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,2-8°C
solubility almost transparency in N,N-DMF
pka3.59±0.10(Predicted)
form powder to crystal
color White to Light yellow
BRN 5178656
Major Applicationpeptide synthesis
InChIKeyRZRRJPNDKJOLHI-QFIPXVFZSA-N
SMILES[N+](=O)([O-])c1ccc(cc1)C[C@H](NC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O
CAS DataBase Reference95753-55-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Safety Statements 22-24/25
WGK Germany 3
HS Code 2924 29 70
HazardClass IRRITANT
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
Fmoc-4-nitro-L-phenylalanine Usage And Synthesis
Chemical PropertiesWhite powder
UsesFmoc-Phe(4-NO2)-OH is used to prepare squaric acid derivatives as VLA-4 integrin antagonists. It is also an intermediate used in the synthesis of analogs of kahalalide F.
reaction suitabilityreaction type: Fmoc solid-phase peptide synthesis
Synthesis
4-Nitro-3-phenyl-L-alanine

949-99-5

N-(9-Fluorenylmethoxycarbonyloxy)succinimide

82911-69-1

Fmoc-4-nitro-L-phenylalanine

95753-55-2

GENERAL STEPS: 37.7 g (0.179mol) of (S)-2-amino-3-(4-nitrophenyl)propionic acid was suspended in 200 mL of a 2% NaOH aqueous solution, and 80 mL of acetonitrile was added until completely dissolved. To this solution was added 61.8 g (0.183 mol) of 9-fluorenylmethyl-N-succinimidyl carbonate suspended in 100 mL of acetonitrile. The reaction mixture was stirred at room temperature for 3 h and subsequently acidified to pH 4-5 with 5% HCl. The precipitated white crystals were collected by filtration, washed with ethyl acetate and dried. The product was recrystallized by ethanol-dioxane (50:50) solvent mixture. The yields were 67% (3a) and 71% (3b), respectively. The melting point was 230 °C (literature value 233-234 °C [10]).IR spectrum (ν, cm-1): 3429, 3202, 1724, 1693, 1601, 1520, 1447, 1354, 1223, 1057, 856, 760, 741.1H NMR spectrum (DMSO-d6, δ, ppm): 2.90- 3.09 (m, 1H, CH2), 3.25 (dd, 1H, CH2, 2J=13.7, 3J=4.3 Hz), 4.13-4.34 (m, 4H, 2CH2, 2CH), 7.23-7.45 (m, 4Harom), 7.54 (d, 2Harom, 3J=8.6 Hz), 7.60-7.64 (m, 2Harom), 7.79 (d, 1H, NH, 3J=8.6 Hz), 7.88 (d, 2Harom, 3J=7.5 Hz), 8.14 (d, 2Harom, 3J=8.6 Hz), 12.93 (s, 1H, COOH).13C NMR spectra (DMSO-d6, δ, ppm): 36.62 (CH2) 47.03 (CH), 55.25 (CH), 66.03 (CH2), 120.56, 123.69, 125.62, 127.45, 128.07, 130.94, 141.16, 144.20, 146.73 (arom), 156.39 (CONH), 173.27 (COOH). Mass spectrum (ESI, m/z): 455.1214 [M+Na]+. Molecular formula C24H20N2O6, calculated molecular weight 432.1321.

References[1] Tetrahedron Letters, 1999, vol. 40, # 36, p. 6557 - 6560
[2] Russian Journal of Organic Chemistry, 2016, vol. 52, # 11, p. 1681 - 1685
[3] Zh. Org. Khim., 2016, vol. 52, # 11, p. 1686 - 1690,5
Tag:Fmoc-4-nitro-L-phenylalanine(95753-55-2) Related Product Information
9-Fluorenylmethyl chloroformate Fmoc-Phe-OH Phenprobamate 4-Nitro-3-phenyl-L-alanine D-Phenylalanine Fmoc-Aib-OH N-(tert-Butoxycarbonyl)-L-phenylalanine L-Phenylalanine Fmoc-OSu FMOC-L-4-Methylphe (S)-N-FMOC-4-Chlorophenylalanine Fmoc-Tyr(Me)-OH Fmoc-L-4-Iodophenylalanine FMOC-L-4-Fluorophe (S)-N-Fmoc-Allylglycine Fmoc-d, L-Phe(4-c(o)NH2) Fmoc-L-9-anthrylalanine Fmoc-L-4-cyanophenylalanine