| Identification | More | [Name]
FMOC-TYR(ME)-OH | [CAS]
77128-72-4 | [Synonyms]
FMOC-4-METHOXY-L-PHENYLALANINE
FMOC-4-METHOXYPHENYLALANINE
FMOC-4-METHOXY-PHE-OH
FMOC-L-4-METHOXYPHE
FMOC-L-TYR(ME)
FMOC-L-TYR(ME)-OH
FMOC-L-TYROSINE(METHYL ETHER)
FMOC-O-METHYL-L-TYROSINE
FMOC-PHE(4-OME)-OH
FMOC-P-METHOXY-PHE-OH
FMOC-TYR(ME)-OH
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-4-METHOXY-L-PHENYLALANINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-METHYL-L-TYROSINE
N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-METHY-L-TYROSINE
N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-METHYL-L-TYROSINE
N-ALPHA-FMOC-O-METHYL-L-TYROSINE
(S)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-(4-METHOXY-PHENYL)-PROPIONIC ACID
FMOC-4-METHOXYPHENYLALANINE MIN 99%
Fmoc-L-4-MeO-Phe-OH
FMOC-TYR(AL)-OH | [Molecular Formula]
C25H23NO5 | [MDL Number]
MFCD00153368 | [Molecular Weight]
417.45 | [MOL File]
77128-72-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
161 °C | [Boiling point ]
647.8±55.0 °C(Predicted) | [density ]
1.274±0.06 g/cm3(Predicted) | [storage temp. ]
Store at 0°C | [form ]
powder to crystal | [pka]
2.97±0.10(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C25H23NO5/c1-30-17-12-10-16(11-13-17)14-23(24(27)28)26-25(29)31-15-22-20-8-4-2-6-18(20)19-7-3-5-9-21(19)22/h2-13,22-23H,14-15H2,1H3,(H,26,29)(H,27,28)/t23-/m0/s1 | [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) |
| Hazard Information | Back Directory | [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 | [reaction suitability]
reaction type: Fmoc solid-phase peptide synthesis | [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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