Fmoc-O-sulfo-L-tyrosine sodium salt

• CAS: 106864-37-3
• Catalog Number: ACM106864373
• Category: Main Products
• Molecular Weight: 505.48
• Molecular Formula: C₂₄H₂₀NNaO₈S
• IUPAC Name: Sodium N-[(9H-fluoren-9-ylmethoxy)carbonyl]-O-sulfonato-D-tyrosin e
• Appearance: White powder
• Exact Mass: 509.11200

Case Study

A Simple Solid-Phase Synthesis Strategy for Sulfated Tyrosine Peptides

Kitagawa K, et al. The Journal of organic chemistry, 2001, 66(1), 1-10.

Fmoc-based solid-phase peptide synthesis (Fmoc-SPPS) enables us to directly construct sulfated peptide chains using Fmoc-Tyr-(SO3Na)-OH (Fmoc-O-sulfo-L-tyrosine sodium salt) as building blocks (preassembly sulfation). This work developed an efficient acidolysis system for Tyr(SOH)-containing peptides. This deprotection system was combined with 2-chlorotrityl resin, which is highly sensitive to acid, as a solid carrier to establish a general synthesis strategy for sulfated peptides.
Desulfation vs Deprotection: Kinetic Studies
· Fmoc-Tyr(SO3Na)-OH (4.28 mg, 8.47 µmol), Fmoc-Ser(t Bu)-OH (3.25 mg, 8.47 µmol), and Fmoc-Arg(Pbf)- OH (5.50 mg, 8.47 µmol) were separately dissolved in TFA (1.0 mL) and stirred at a specified temperature (0, 18, or 30 °C).
· At appropriate intervals, 5.0 µL of each solution was withdrawn and diluted with a mixture of CH3CN and phosphate buffer (0.2 M, pH 7.0).
· Part of this solution (200 µL) was analyzed by RP-HPLC (elution system, a linear gradient of CH3CN in 0.1 M AcONH4; flow rate, 1 mL/min; absorbance was detected at 300 nm].
· Under these chromatographic conditions, the tR of the starting compounds and the reaction products were as follows: 4.8 and 7.8 min for FmocTyr(SO3Na)-OH and Fmoc-Tyr-OH; 10.8 and 6.3 min for FmocSer(t Bu)-OH and Fmoc-Ser-OH; 14.1 and 6.1 min for FmocArg(Pbf)-OH and Fmoc-Arg-OH, respectively.