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)

Safety Information

WGK Germany 

WGK 2 water endangering

HazardClass 

IRRITANT

HS Code 

29242990

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.

Fmoc-Tyr(Me)-OH(77128-72-4)Related Product Information

• FMOC-TYR(BZL)-OH 98%,FMOC-TYR(BZL)-OH
• N-Fmoc-O-Phenyl-L-Tyrosine
• Fmoc-Tyr(Ac)-OH
• FMOC-L-4-Fluorophe
• Fmoc-L-4-Iodophenylalanine
• (S)-N-FMOC-4-Chlorophenylalanine
• FMOC-L-9-ANTHRYLALANINE
• FMOC-D, L-PHE(4-C(O)NH2)
• FMOC-L-4-Methylphe
• Fmoc-4-nitro-L-phenylalanine
• (S)-N-Fmoc-Allylglycine
• FMOC-L-4-CYANOPHENYLALANINE
• FMOC-TYR(ET)-OH
• FMOC-TYR(ALL)-OH,FMOC-TYR(AL)-OH
• FMOC-TYR(2-BR-Z)-OH
• FMOC-TYR(MALONYL-DI-OTBU)-OH
• Fmoc-Tyr(tBu)-OH
• Fmoc-Tyr(Me)-OH