FMOC-O-tert-Butyl-L-serine (CAS 71989-33-8)

Product Name: FMOC-O-tert-Butyl-L-serine

CAS Number: 71989-33-8

Molecular Formula: C₂₂H₂₅NO₅

Molecular Weight: 395.44 g/mol

Appearance: White to off-white crystalline powder

Purity: ≥98% (HPLC)

Storage: Store at 2-8°C in a dry, dark environment

Intended Use

FMOC-O-tert-Butyl-L-serine (CAS 71989-33-8) is a protected amino acid derivative widely used in:

• Solid-phase peptide synthesis (SPPS) as a building block
• Protection of serine hydroxyl groups during organic reactions
• Pharmaceutical research for drug candidate development
• Bioconjugation and chemical biology applications

The FMOC (9-fluorenylmethyloxycarbonyl) group ensures selective deprotection, while the tert-butyl group provides steric protection for sensitive functional groups.

Usage Guidelines

1. Solubility: Dissolve in DMF, DCM, or THF (10-20 mg/mL)
2. Coupling Conditions: Use HBTU/HOBt or DIC/Oxyma in DMF at room temperature
3. Deprotection: Remove FMOC group with 20% piperidine in DMF (2 × 5 min)
4. Storage: Keep container tightly sealed under inert gas to prevent hydrolysis

Note: Always use personal protective equipment (gloves, goggles) when handling.

Application Cases

Case Study 1: Anticancer Peptide Synthesis

In the development of kinase inhibitor peptides, researchers utilized FMOC-O-tert-Butyl-L-serine to:

1. Couple with FMOC-L-lysine(Boc) on Rink amide resin
2. Perform iterative SPPS cycles using automated synthesizers
3. Cleave final peptide with TFA cocktail (95% TFA, 2.5% H₂O, 2.5% TIPS)
4. Purify via reverse-phase HPLC (C18 column, acetonitrile/water gradient)

Case Study 2: Glycopeptide Production

For O-linked glycopeptide synthesis:

1. Incorporate FMOC-protected serine at position 4 of the peptide chain
2. Remove FMOC group while retaining tert-butyl protection
3. Perform glycosylation using trichloroacetimidate donors
4. Final global deprotection with TFA to yield bioactive glycopeptides