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Fmoc-Tyr(Me)-OH

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Fmoc-Tyr(Me)-OH Basic information

Product Name:
Fmoc-Tyr(Me)-OH
Synonyms:
  • Fmoc-4-Methoxy-L-Phe-OH
  • Methoxy phenylalanine
  • N-FMoc-4-Methoxy-L-phenylalanine, 95%
  • FMoc-Tyr(Me)-OH FMoc-O-Methyl-L-tyrosine
  • FMOC-(S)-b-(p-Methoxyphenyl)alanine
  • (S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-(4-Methoxyphenyl)propanoic acid
  • N-Fmoc-O-methyl-L-tyrosine, >=99%
  • Fmoc-4-Methoxy-Phe
CAS:
77128-72-4
MF:
C25H23NO5
MW:
417.45
Product Categories:
  • Phenylalanine [Phe, F]
  • Unusual Amino Acids
  • Amino Acids
  • Fmoc-Amino acid series
Mol File:
77128-72-4.mol
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Fmoc-Tyr(Me)-OH Chemical Properties

Melting point:
161 °C
Boiling point:
647.8±55.0 °C(Predicted)
Density 
1.274±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
pka
2.97±0.10(Predicted)
form 
powder to crystal
color 
White to Almost white
InChIKey
JYQODLWFOPCSCS-QHCPKHFHSA-N
SMILES
C(O)(=O)[C@H](CC1=CC=C(OC)C=C1)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O
CAS DataBase Reference
77128-72-4(CAS DataBase Reference)
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Safety Information

WGK Germany 
WGK 2 water endangering
HazardClass 
IRRITANT
HS Code 
29242990
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Fmoc-Tyr(Me)-OH Usage And Synthesis

Description

Fmoc-Tyr(Me)-OH, also known as Fmoc-O-methyl-L-tyrosine, is an Fmoc protected tyrosine derivative that is potentially useful for proteomics studies and solid phase peptide synthesis techniques. Tyrosine is a important amino acid - one of the few amino acids which is phosphorylated to vary the physical properties of the peptides, and is a precursor for the formation of iodinated thyroid hormones. The Fmoc group is typically removed with a base such as pyridine - an orthogonal de-protection strategy to the acid labilie Boc group.

Chemical Properties

White to off-white powder

Synthesis

Fmoc-Tyr(Me)-OH, also known as Fmoc-Tyr(OMe)-OH, was obtained from Fmoc-Tyr(OMe)-OMe within 1h and was isolated following protocol 1 or 2 in 96% yield[1]. Under argon atmosphere, anhydrous THF (2.0 mL) was added to the protected amino acid  Fmoc-Tyr(OMe)-OMe (0.12 mmol) and to MgI2 * (1.2 mmol). The suspension was heated in a sealed reactor using microwave irradiation at 120°C. A Na2S2O3 aqueous solution (0.1 M) was then added and the resulting homogeneous mixture was directly analysed by analytical HPLC and LC/MS. To isolate the product, two protocols could be applied:
Protocol 1: The crude material was purified by preparative HPLC.
Protocol 2: The crude material was extracted with AcOEt (x3). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was diluted in H2O/EtOH and lyophilized.

References

[1] Berthet M, et al. MgI2 -Mediated Chemoselective Cleavage of Protecting Groups: An Alternative to Conventional Deprotection Methodologies. Chemistry - A European Journal, 2015; 21: 11014-11016.

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