134150-51-9

Usage

Uses

Used in Biochemistry Research:
FMOC-TYR(PO3BZL2)-OH is utilized as a research tool for studying the role of phosphorylation in various biological processes. Its phosphate mimic capability allows scientists to observe and understand the effects of phosphorylation on protein function and cellular signaling.
Used in Peptide Chemistry:
In peptide chemistry, FMOC-TYR(PO3BZL2)-OH is employed as a building block for the synthesis of peptides containing phosphorylated tyrosine residues. The FMOC protecting group ensures the stability of the compound during synthesis and allows for its selective removal when required.
Used in Drug Development:
FMOC-TYR(PO3BZL2)-OH serves as a key component in the development of drugs that target protein phosphorylation, which is a common regulatory mechanism in cellular processes. By incorporating FMOC-TYR(PO3BZL2)-OH into drug molecules, researchers can design therapies that modulate cellular signaling pathways associated with various diseases.
Used in the Pharmaceutical Industry:
FMOC-TYR(PO3BZL2)-OH is used as an intermediate in the synthesis of pharmaceuticals that require phosphorylated tyrosine residues. Its application ensures the accurate replication of biologically active molecules, contributing to the development of effective treatments for a range of conditions.
Used in Diagnostics:
In the diagnostics field, FMOC-TYR(PO3BZL2)-OH can be used to develop assays for detecting the presence or activity of enzymes involved in protein phosphorylation. This can aid in the diagnosis and monitoring of diseases where abnormal phosphorylation events occur.
Overall, FMOC-TYR(PO3BZL2)-OH is a versatile compound with applications spanning across various scientific and medical disciplines, underscored by its unique structural features that facilitate the study and manipulation of phosphorylation-dependent processes.

InChI:InChI=1/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

Upstream product

• 134150-54-2 C₃₀H₃₅NO₅Si 
• 112883-29-1 N-Fmoc-Tyr-OH 
• 67746-43-4 dibenzyl N,N-diethylphosphoramidite 
• 146346-83-0 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-(tertbutyldimethylsilyloxy)phenyl)propanoic acid 

Downstream Products

• 1214175-11-7 Ac-RpYVTVNG-NH₂ 
• 1268157-66-9 O-[bis(benzyloxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N'-[3-(2-oxotetrahydropyrimidin-1(2H)-yl)propyl]-L-tyrosinamide 
• 943967-85-9 C₃₃H₅₁N₈O₁₄P 
• 943967-84-8 C₄₂H₆₀N₉O₁₈P 
• 943967-83-7 C₄₂H₆₀N₉O₁₈P 
• 229171-82-8 (S)-4-[(S)-3-[4-(Bis-benzyloxy-phosphoryloxy)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-4-(4-methoxy-benzylcarbamoyl)-butyric acid benzyl ester 
• 191348-16-0 (S)-3-[4-(Benzyloxy-hydroxy-phosphoryloxy)-phenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 

Relevant academic research and scientific papers

Preparation and Use of Nα-Fluorenylmethoxycarbonyl-O-dibenzylphosphono-L-tyrosine in Continuous Flow Solid Phase Peptide Synthesis

Nα-Fluorenylmethoxycarbonyl-O-dibenzylphosphono-L-tyrosine is a useful derivative for the solid phase synthesis of O-phosphotyrosine peptides.

Development of non-peptide ligands of growth factor receptor-bound protein 2-src homology 2 domain using molecular modeling and NMR spectroscopy

We report a novel series of non-peptide ligands that inhibit the growth factor receptor-bound protein 2 (Grb2)-Src homology 2 (SH2) domain binding, designed using a combined computational and NMR-driven approach. We have identified a new lead compound, 1n (IC50 = 56 μM), which is cytotoxic in HER2-positive breast cancer cells and disrupts the interaction between HER2 and Grb2. Thus, 1n can be used as a scaffold for the development of efficient Grb2-SH2 domain binding inhibitors.

The synthesis of phosphopeptides via the Bpoc-based approach

The 2-(p-biphenylyl)-2-propyloxycarbonyl (Bpoc) group was examined as an Nα-protecting group in the stepwise assembly of the MAP Kinase ERK2 [178-188; Thr(P)183, Tyr(P)185] peptide. The mild acid deprotection of the Bpoc group permitted (i) incorporation of a fully protected phosphothreonyl derivative and (ii) a TFA-based final cleavage step. The first five C-terminal residues (184-188) were incorporated in the Fmoc mode of peptide synthesis, with all subsequent amino acids coupled as their Bpoc-Xxx-OH derivatives. The target product was obtained in high purity and yield, indicating that a Bpoc-based approach to phosphopeptide synthesis was compatible with both the acid-labile side chain protecting groups employed and Hmp-Wang resin. This journal is The Royal Society of Chemistry.

Alternative Strategies for the Fmoc Solid-Phase Synthesis of O4-Phospho-L-tyrosine-Containing Peptides

A number of biologically relevant O4-phospho-L-tyrosine-containing peptides have been synthesized by either the global phosphorylation of the side-chain-unprotected L-tyrosine moiety in presynthesized resin-bound peptides or alternatively by the incorporation of suitable protected O4-phospho-L-tyrosine building blocks in the continuous-flow method of Fmoc solid-phase peptide synthesis.Different phosphate-protecting groups have been applied.