Fmoc-Tyr(2,6-Me2,4-tBu)-OH, 1043043-79-3, IC-0191265
Product Introduction
Fmoc-Tyr(2,6-Me2,4-tBu)-OH is an Fmoc-protected tyrosine derivative bearing a 2,6-dimethyl-4-tert-butyl substitution on the phenolic ring. The bulky 2,6-dimethyl and 4-tert-butyl groups protect the phenolic hydroxyl from side reactions such as acylation, alkylation, and oxidation during solid-phase peptide synthesis (SPPS), eliminating the need for additional phenolic protecting groups. The increased steric bulk also modulates the conformational properties of the resulting peptides and can influence aggregation behavior, making this building block valuable for the synthesis of challenging peptide sequences. This derivative is compatible with standard Fmoc-based SPPS protocols and is particularly useful for the synthesis of phosphotyrosine-containing peptides, sulfated peptides, and peptides requiring phenolic hydroxyl protection without labile ester linkages.
Product Features
1. Built-In Phenol Protection: 2,6-Dimethyl-4-tert-butyl substitution protects the phenolic hydroxyl from side reactions during SPPS.
2. No Additional Protecting Group Required: Eliminates the need for separate phenolic protecting groups and their deprotection steps.
3. Fmoc-Compatible: Fully compatible with standard Fmoc-based SPPS protocols and coupling reagents.
4. Modulates Peptide Properties: Steric bulk can influence peptide conformation, solubility, and aggregation behavior.
5. High Purity: Supplied at ¡Ý99% purity for reproducible peptide synthesis.
Specifications
Size: 100 mg / 1 g
CAS Number: 1043043-79-3
Purity: ¡Ý99%
Molecular Weight: 499.60
Molecular Formula: C30H33NO5
Appearance: White to off-white powder
Solubility: DMF: ¡Ý50 mg/mL; DMSO: ¡Ý50 mg/mL; DCM: ¡Ý20 mg/mL
Storage and Stability
Storage Conditions: Store sealed in dry conditions at 2-8¡ãC, protected from light and moisture.
Shelf Life: The product is stable for 24 months from the date of manufacture when stored as directed.
Protocol (For Reference Only)
Important: Protect from light and moisture. Use anhydrous solvents for coupling reactions.
1. Stock Solution Preparation: Dissolve Fmoc-Tyr(2,6-Me2,4-tBu)-OH in anhydrous DMF or DCM to prepare a coupling solution at the desired concentration (e.g., 0.3-0.5 M).
2. Solid-Phase Peptide Synthesis: Incorporate the derivative into the growing peptide chain using standard Fmoc SPPS coupling reagents (e.g., HCTU/DIPEA, HBTU/HOBt, DIC/Oxyma) according to established protocols.
3. Fmoc Deprotection: Remove the Fmoc protecting group using 20% piperidine in DMF according to standard protocols.
4. Cleavage and Deprotection: Cleave the peptide from the resin using standard cleavage cocktails (e.g., TFA/TIS/H2O). The 2,6-dimethyl-4-tert-butyl phenol protecting group is removed under standard TFA cleavage conditions.
5. Characterization: Confirm peptide identity and purity by HPLC and mass spectrometry.
Precautions
1. Protect from light and moisture during storage and handling.
2. Use anhydrous solvents for coupling reactions to prevent hydrolysis of activated intermediates.
3. The bulky side-chain protecting group may require extended coupling times for sterically demanding sequences.
4. For research use only. Not for use in diagnostic or therapeutic procedures.
FAQ (Simplified)
Q1: What is the purpose of the 2,6-dimethyl-4-tert-butyl substitution?
A1: The bulky substitution protects the phenolic hydroxyl from side reactions such as acylation, alkylation, and oxidation during SPPS, eliminating the need for additional phenolic protecting groups.
Q2: Is this derivative compatible with standard Fmoc SPPS?
A2: Yes. It is fully compatible with standard Fmoc-based SPPS protocols and coupling reagents.
Q3: How is the protecting group removed?
A3: The 2,6-dimethyl-4-tert-butyl phenol protecting group is removed under standard TFA cleavage conditions.
Q4: How should I store this product?
A4: Store sealed in dry conditions at 2-8¡ãC, protected from light and moisture.
Disclaimer
1. For Research Use Only. Not for use in diagnostic or therapeutic procedures.
2. Due to the variable nature of peptide synthesis, optimization of coupling conditions is recommended for specific sequences.
3. This warranty is limited to the replacement of the product. The manufacturer assumes no liability for incidental or consequential damages.
4. Wear appropriate protective clothing and gloves when handling this product.
Ordering Information
Catalog Number: IC-0191265
Product Name: Fmoc-Tyr(2,6-Me2,4-tBu)-OH
Size: 100 mg / 1 g
Suggested Retail Price:
100 mg: CNY ¥2600.00 / USD $260.00 / EUR €312.00 / JPY ¥46800.00
1 g: CNY ¥6750.00 / USD $675.00 / EUR €810.00 / JPY ¥121500.00
Note: The specific price is subject to the transaction price in the offline contract. This document is provided for technical reference only and does not constitute any form of sales advertisement or invitation to offer. For product details and purchase inquiries, please contact local sales representatives.
