N-Boc-O-benzyl-L-serine (CAS 23680-31-1): Comprehensive User Guide & Application Insights
Table of Contents
1. Product Overview & Specifications
| Parameter | N-Boc-O-benzyl-L-serine | CAS 23680-31-1 |
|---|---|---|
| Molecular Formula | C₁₅H₂₁NO₅ | Verified |
| Molecular Weight | 295.33 g/mol | ±0.5% |
| Purity | >99% (HPLC) | USP/EP Grade |
| Storage | 2-8°C in inert atmosphere | |
Key advantage: Dual protection (Boc for amine, Benzyl for hydroxyl) enables selective deprotection in multi-step syntheses.
2. Key Applications in Organic Synthesis
2.1 Peptide Synthesis
Enables side-chain protection during solid-phase peptide synthesis (SPPS) with:
- Orthogonal protection strategy compatibility
- Stability under TFA cleavage conditions
2.2 PROTAC Molecules
Critical for constructing E3 ligase-binding motifs in targeted protein degradation systems.
3. Case Study: Peptide Drug Intermediate Production
Client: Shanghai InnovPharma (GMP-certified facility)
Challenge: Achieve >90% yield in cGMP-compliant somatostatin analog synthesis.
Solution: Implemented Boc/Benzyl protection for:
| Step | Result |
|---|---|
| Coupling efficiency | 92.4% (vs 85% with Fmoc) |
| Deprotection time | Reduced by 40% |
4. Case Study: PROTAC Molecule Development
Client: Hangzhou TargetRx Biotech
Application: Construction of VHL E3 ligase-recruiting module for BTK degrader:
- Maintained chiral integrity during linker attachment
- Enabled selective benzyl removal via hydrogenolysis
Outcome: Achieved DC₅₀ of 1.2 nM in cellular assays.
5. Performance Comparison
| Protecting Group | Acid Stability | Base Stability | Deprotection Method |
|---|---|---|---|
| Boc | Moderate | High | TFA |
| Fmoc | Low | High | Piperidine |
| Benzyl | High | Low | H₂/Pd |
6. Technical Support & Ordering
Contact our peptide chemistry experts:
Email: info@vivalr.com
Tel: (86) 15866781826
Customization available: Bulk quantities (100g-10kg), chiral purity optimization, technical packages including MSDS and COA.
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