Introduction

Fmoc-Tyr(tBu)-Ser(ψMe,Me,Pro)-OH (CAS 878797-09-2) is an advanced pseudoproline dipeptide building block designed to overcome challenges in solid-phase peptide synthesis (SPPS). Combining the Fmoc-protected tyrosine derivative, a tert-butyl (tBu)-protected hydroxyl group, and a serine-derived pseudoproline (ψPro) motif, this compound enhances solubility, reduces aggregation, and improves yields during the synthesis of complex or aggregation-prone peptide sequences. Its CAS number, 878797-09-2, ensures precise identification in research and industrial workflows. This article explores its structural features, applications, and advantages in modern peptide chemistry.

Chemical Structure and Key Components

Fmoc-Tyr(tBu)-Ser(ψMe,Me,Pro)-OH (CAS 878797-09-2) integrates three critical elements:

1. Fmoc Protecting Group: Shields the α-amino group, enabling sequential deprotection with piperidine during SPPS.

2. Tyr(tBu): Tyrosine with a tert-butyl-protected phenolic hydroxyl group, preventing side reactions during synthesis.

3. Ser(ψMe,Me,Pro): A pseudoproline motif derived from serine, where the hydroxyl group is converted into a thioether-linked dimethylproline structure. This modification disrupts β-sheet formation, minimizing peptide chain aggregation.

The CAS registry 878797-09-2 uniquely identifies this compound, streamlining sourcing and regulatory compliance.

Applications in Peptide Synthesis

1. Synthesis of Aggregation-Prone Sequences

The ψPro motif in CAS 878797-09-2 breaks rigid secondary structures (e.g., β-sheets), enabling efficient elongation of peptides prone to aggregation, such as amyloid-β fragments or hydrophobic antimicrobial peptides.

2. Improved Solubility and Yield

Pseudoprolines enhance solubility in SPPS solvents (e.g., DMF), reducing truncated sequences and improving overall synthesis yields by up to 30% compared to standard dipeptides.

3. Conformational Studies

Used to introduce kinks or turns in peptides for structural biology studies (e.g., NMR or X-ray crystallography), aiding the analysis of protein folding mechanisms.

4. Therapeutic Peptide Development

• Anticancer Peptides: Stabilizes membrane-targeting peptides with improved tumor penetration.

• Hormone Analogues: Facilitates synthesis of glucagon-like peptide-1 (GLP-1) derivatives with enhanced bolic stability.

Advantages Over Conventional Dipeptides

• Aggregation Suppression: ψPro motifs prevent chain aggregation, enabling synthesis of "difficult" sequences.

• Orthogonal Protection: Fmoc and tBu groups allow selective deprotection, compatible with acid-sensitive residues.

• Scalability: Integrates seamlessly into automated SPPS platforms for high-throughput production.

Synthesis and Handling Guidelines

Synthesis Protocol:

1. Pseudoproline Formation: Serine is converted to the ψMe,Me,Pro derivative via thioether linkage with dimethylproline.

2. Fmoc Protection: The N-terminus is protected using Fmoc-Cl.

3. Purification: Isolated via reverse-phase HPLC to ≥95% purity.

Storage:

• Store at -20°C in a desiccated environment to prevent hydrolysis of the ψPro moiety.

• Avoid prolonged exposure to light or acidic/basic conditions.

Safety and Regulatory Insights

• Handling: Use gloves and goggles to avoid skin/eye contact; handle in a fume hood.

• Disposal: Follow local regulations for organic waste containing Fmoc or pseudoproline derivatives.

• Regulatory Status: Listed under CAS 878797-09-2, classified as non-hazardous with standard laboratory precautions.

Global Supplier: Pukang Biotechnology

Pukang Biotechnology supplies high-purity Fmoc-Tyr(tBu)-Ser(ψMe,Me,Pro)-OH (CAS 878797-09-2) alongside custom peptide synthesis services. Their offerings include:

• GMP-Grade Material: For preclinical and clinical-stage therapeutic development.

• Technical Support: Optimization of ψPro incorporation strategies for challenging sequences.

• Fast Global Delivery: Ensuring timely access to critical reagents.

Contact: +86-137-0808-4407 | export@pu-kang.com

Conclusion

Fmoc-Tyr(tBu)-Ser(ψMe,Me,Pro)-OH (CAS 878797-09-2) revolutionizes peptide synthesis by addressing aggregation and solubility challenges, particularly in complex or hydrophobic sequences. Its pseudoproline technology enhances yields, supports structural studies, and accelerates the development of therapeutic peptides for oncology, bolic disorders, and neurodegenerative diseases. For researchers tackling "undruggable" targets, CAS 878797-09-2 represents a cornerstone of innovation in peptide chemistry.