181952-24-9

Basic information

• Product Name: Fmoc-Tyr(SO3H)-OH
• Synonyms: Fmoc-Tyr(SO3H)-OH;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(hydroxysulfonyl)-L-tyrosine;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(sulfooxy)phenyl)propanoic acid
• CAS NO: 181952-24-9
• Molecular Formula: C₂₄H₂₁NO₈S
• Molecular Weight: 483.49
• Mol File: 181952-24-9.mol

Chemical Properties

• Appearance: /
• Density: 1.467
• PKA: -4.13±0.18(Predicted)
• CAS DataBase Reference: Fmoc-Tyr(SO3H)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-Tyr(SO3H)-OH(181952-24-9)
• EPA Substance Registry System: Fmoc-Tyr(SO3H)-OH(181952-24-9)

Safety Data

• Hazardous Substances Data: 181952-24-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-Tyr(SO3H)-OH is used as a building block for the synthesis of modified peptides for various pharmaceutical applications. The introduction of the sulfonic acid group can enhance the solubility and stability of the peptide, as well as its interaction with biological targets, leading to improved therapeutic efficacy.
Used in Research and Development:
In the field of research and development, Fmoc-Tyr(SO3H)-OH is employed as a key component in the design and synthesis of novel peptides with specific biological activities. The modification of tyrosine residues allows for the exploration of structure-activity relationships and the development of peptides with tailored properties for use in biological studies and potential therapeutic applications.
Used in Peptide Drug Design:
Fmoc-Tyr(SO3H)-OH is utilized as a crucial component in the design of peptide drugs, where the modified tyrosine residues can confer unique pharmacological properties. The negative charge from the sulfonic acid group can influence the peptide's binding affinity to receptors or enzymes, potentially leading to the discovery of new drug candidates with improved potency and selectivity.
Used in Biochemical Analysis:
In biochemical analysis, Fmoc-Tyr(SO3H)-OH serves as a reagent for the modification of peptides to study their interactions with other biomolecules. The altered chemical properties of the modified tyrosine residues can provide insights into the molecular mechanisms underlying peptide-protein or peptide-nucleic acid interactions, contributing to a better understanding of biological processes.

Upstream product

• 112883-29-1 N-Fmoc-Tyr-OH 

Downstream Products

• 1334600-13-3 5-FAM-Y(SO₃H)EEI-OH 

Relevant articles and documents

Synthesis and anti-HIV activity of nonatyrosine N- and O1-9-decasulfate

To develop a potent and effective anti-HIV compound with a definite polyanionic structure, synthesis of oligotyrosine sulfates by oligomerization with simultaneous sulfation of tyrosine was tried. One component was successfully isolated from the mixture containing many products as its sodium salt (Y-ART-4) and was identified as the salt of nonatyrosine N- and O1-9-decasulfate, NaO3S-[Tyr(SO3Na)]9-ONa. Anti-HIV activity of Y-ART-4, determined from the protection it provided against HIV-induced cytopathic effects, was almost the same with that of dextran sulfate and curdlan sulfate.

Method for preparing tyrosine-O-sulfonate

The invention relates to a method for preparing tyrosine-O-sulfonate. The method comprises the following steps that 1, a sulfoating reagent reacts with Fmoc-protected tyrosine in the presence of a thinner and alkali to obtain a reaction solution; 2, the reaction solution obtained in the step 1 is poured into a poor solvent, and then standing is conducted; 3, a supernatant solution of a product obtained in the step 2 is poured out, residues are dissolved with water, and the pH is regulated to be weakly acidic through alkali; 4, an aqueous solution obtained in the step 3 is washed with a good solvent and then concentrated; 5, the good solvent is added into a concentrate product obtained in the step 4, stirring and filtering are sequentially conducted, filtrate is added into the poor solvent, stirring is conducted, solids are collected and dried, and the solid product is obtained. According to the method, the problems that when distillation, freeze-drying and the like are applied, long time is consumed, and the equipment requirements are high are avoided; by additionally conducting extraction operation in aftertreatment, the purity is greatly improved, and column chromatography purification operation difficult to enlarge is prevented from being applied, and the method is suitable for enlarged production, easy to operate and high in product purity.