Fmoc-Tyr(PO3Bzl2)-OH
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Fmoc-Tyr(PO3Bzl2)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-005336
CAS number
134150-51-9
Molecular Formula
C38H34NO8P
Molecular Weight
663.65
Fmoc-Tyr(PO3Bzl2)-OH
IUPAC Name
(2S)-3-[4-bis(phenylmethoxy)phosphoryloxyphenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
(2S)-3-[4-bis(phenylmethoxy)phosphoryloxyphenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid; Fmoc-pTyr-OH; Nalpha-Fmoc-O-[bis(benzyloxy)phosphoryl]-L-tyrosine; O-[bis(benzyloxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-tyrosine; N2-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O4-(bis(benzyloxy)phosphoryl)-L-tyrosine
Appearance
powder (amorphous)
Purity
≥ 95%
Density
1.321 g/cm3
Boiling Point
818.9 °C at 760 mmHg
Storage
Store at -20 °C
InChI
InChI=1S/C38H34NO8P/c40-37(41)36(39-38(42)44-26-35-33-17-9-7-15-31(33)32-16-8-10-18-34(32)35)23-27-19-21-30(22-20-27)47-48(43,45-24-28-11-3-1-4-12-28)46-25-29-13-5-2-6-14-29/h1-22,35-36H,23-26H2,(H,39,42)(H,40,41)/t36-/m0/s1
InChI Key
JSTYRDUOBZALLV-BHVANESWSA-N
Canonical SMILES
C1=CC=C(C=C1)COP(=O)(OCC2=CC=CC=C2)OC3=CC=C(C=C3)CC(C(=O)O)NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
1. Efficient solid phase synthesis of mixed Thr(P)-, Ser(P)- and Tyr(P)-containing phosphopeptides by "global" "phosphite-triester" phosphorylation
J W Perich Int J Pept Protein Res. 1992 Aug;40(2):134-40.
The synthesis of the mixed Thr(P)/Tyr(P)-containing peptide, Ala-Thr(P)-Tyr(P)-Ser-Ala, was accomplished by "phosphite-triester" phosphorylation of the resin-bound Thr/Tyr-containing peptide using di-t-butyl N,N-diethylphosphoramidite as the phosphitylation reagent. The pentapeptide-resin was assembled by Fmoc/solid-phase peptide synthesis with the use of PyBOP as coupling reagent and the hydroxy-amino acids incorporated as side-chain free Fmoc-Tyr-OH and Fmoc-Thr-OH. "Global" bis-phosphorylation of the peptide-resin was accomplished by treatment with di-t-butyl N,N-diethylphosphoramidite/1H-tetrazole followed by m-chloroperoxybenzoic acid oxidation of the intermediate di-t-butylphosphite triester. Simultaneous peptide-resin cleavage and peptide deprotection was effected by treatment of the peptide-resin with 5% anisole/TFA and gave the Thr(P)/Tyr(P)-containing phosphopeptide in high yield and purity. In addition, the tyrosyl residue was found to be phosphitylated in preference to the threonyl residue since the phosphitylation of the pentapeptide-resin using only 1.1 equiv. of di-t-butyl N,N-diethylphosphoramidite gave Ala-Thr-Tyr(P)-Ser-Ala as the major product and both Ala-Thr(P)-Tyr(P)-Ser-Ala and Ala-Thr-Tyr-Ser-Ala as minor products.
2. Solid phase synthesis of pp60src-related phosphopeptides via 'global' phosphorylation and their use as substrates for enzymatic phosphorylation by casein kinase-2
J W Perich, F Meggio, L A Pinna Bioorg Med Chem. 1996 Feb;4(2):143-50. doi: 10.1016/0968-0896(95)00163-8.
The seven phosphopeptide derivatives based on the native -NEYTA- sequence of the pp60src protein kinase family, Asn-Glu-Tyr(P)-Ser-Ala, Ala-Glu-Tyr(P)-Ser-Ala, Ala-Ser-Tyr(P)-Ser-Ala, Ala-Ser(P)-Tyr-Ser-Ala, Ala-Thr-Tyr(P)-Ser-Ala, Ala-Thr(P)-Tyr-Ser-Ala and Ala-Ser(P)-Tyr(P)-Ser-Ala, were prepared in good yield using the "global' "phosphite-triester' phosphorylation method. The peptide resins were assembled using the Fmoc mode of solid phase peptide synthesis (PyBOP coupling method) with specific Ser-, Thr-, or Tyr-residues incorporated as their side chain free Fmoc-derivatives. The final "global' phosphorylation of the peptide resins was accomplished using di-tert-butyl N, N-diethylphosphoramidite followed by m-chloroperoxybenzoic acid oxidation of the resultant di-t-butyl phosphite triester intermediate. Subsequent resin cleavage and deprotection of the phosphorylated peptide resins was effected by treatment with 5% anisole: TFA and gave the seven phosphopeptides in high yield and purity. The use of the seven synthetic phosphopeptides in enzymatic (casein kinase-2) phosphorylation studies showed that, (A) the change of the target Thr site to Ser resulted in markedly improved phosphorylation of the peptide substrates, (B) that the Tyr(P) residue in the - 1 position was significantly more important than the Ser(P)/Thr(P) residue in the - 2 position for efficient seryl phosphorylation, and (C) that an acidic residue in the - 2 position relative to the target site facilitated phosphorylation of the downstream seryl residue irrespective of the nature of the acidic residue in the -Xxx-Tyr(P)-Ser- and -Xxx-Tyr-Ser- sequences {Xxx = Ser(P), Thr(P), Glu}. In addition to the Tyr(P) residue directing phosphorylation to the +1 position, the good phosphorylation of both ASY(P)SA and ATY(P)SA by casein kinase-2 indicated that the Tyr(P) residue was also able to direct phosphorylation to a Ser/Thr in the - 1 position.
3. Phosphorylation of src-phosphopeptides by casein kinases-1 and -2: favourable effect of phosphotyrosine
J W Perich, F Meggio, E A Kitas, R M Valerio, R B Johns, L A Pinna Biochem Biophys Res Commun. 1990 Jul 31;170(2):635-42. doi: 10.1016/0006-291x(90)92139-q.
The synthetic phosphotyrosyl tridecapeptide H-Arg-Leu-Ile-Glu-Asp-Asn-Glu-Tyr(P)-Thr-Ala-Arg-Gln-Gly-OH, reproducing a major phosphoacceptor site of protein tyrosine kinases of the src-family, can be phosphorylated at Thr-9 by both casein kinases -1 and -2. Its shorter derivative H-Asn-Glu-Tyr(P)-Thr-Ala-OH is not affected by casein kinase-1 while representing a substrate as good as the tridecapeptide for casein kinase-2. The unphosphorylated analogue H-Asn-Glu-Tyr-Thr-Ala-OH, however, is a much poorer substrate, and no significant phosphorylation could be observed of its O-methyl ether derivative H-Asn-Glu-Tyr(Me)-Thr-Ala-OMe. These data on one side corroborate the concept that casein kinase-1 recognizes residues located on the C-terminal edge of acidic stretches, providing, on the other, the evidence that phosphotyrosyl side chains can act as specificity determinants for casein kinase-2.
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