Introduction

Fmoc-Ala-Ser(ψMe,Mepro)-OH (CAS 252554-78-2) is a pseudoproline dipeptide building block designed to overcome challenges in solid-phase peptide synthesis (SPPS). By integrating the Fmoc (fluorenylmethyloxycarbonyl) protecting group, alanine (Ala), and a serine-derived pseudoproline (ψPro) motif, this compound minimizes peptide chain aggregation, improves solubility, and enhances synthesis efficiency for complex or hydrophobic sequences. Its CAS number, 252554-78-2, ensures precise identification in research and industrial workflows. This article highlights its structural features, applications, and advantages in modern peptide chemistry.

Chemical Structure and Key Components

Fmoc-Ala-Ser(ψMe,Mepro)-OH (CAS 252554-78-2) comprises three critical elements:

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

2. Alanine (Ala): A simple, non-polar amino acid contributing to peptide backbone stability.

3. Ser(ψMe,Mepro): A pseudoproline motif where serine’s hydroxyl group is converted into a thioether-linked methylproline structure. This modification disrupts β-sheet formation, reducing aggregation during synthesis.

The CAS registry 252554-78-2 uniquely identifies this compound, streamlining sourcing and regulatory compliance.

Applications in Peptide Synthesis

1. Synthesis of Aggregation-Prone Peptides

The ψPro motif in CAS 252554-78-2 breaks rigid secondary structures (e.g., β-sheets), enabling efficient synthesis of peptides prone to aggregation, such as amyloid-β or prion protein fragments.

2. Improved Solubility and Yield

Pseudoprolines enhance solubility in SPPS solvents (e.g., DMF or NMP), reducing truncation byproducts and improving overall yields by up to 40% compared to standard dipeptides.

3. Structural Biology and Conformational Studies

Introduces kinks or turns in peptides for X-ray crystallography or NMR studies, aiding analysis of protein folding and interaction mechanisms.

4. Therapeutic Peptide Development

• Antimicrobial Peptides (AMPs): Enhances stability against proteolytic degradation, improving efficacy against multidrug-resistant bacteria.

• Hormone Analogues: Facilitates synthesis of stable glucagon or insulin derivatives for bolic disorder treatments.

Advantages Over Conventional Dipeptides

• Aggregation Suppression: The ψPro motif prevents peptide chain stacking, enabling synthesis of "difficult" sequences.

• Orthogonal Compatibility: Fmoc protection aligns with standard SPPS protocols, avoiding interference with acid-sensitive residues.

• Scalability: Integrates seamlessly into automated peptide synthesizers for high-throughput production.

Synthesis and Handling Guidelines

Synthesis Protocol:

1. Pseudoproline Formation: Serine is modified to incorporate the methylproline thioether linkage.

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

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

Storage:

• Store at -20°C in a dry, dark environment to prevent degradation of the ψPro moiety.

• Avoid exposure to moisture, strong acids, or s.

Safety and Regulatory Insights

• Handling: Use gloves, goggles, and a fume hood to avoid skin/eye contact or inhalation.

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

• Regulatory Status: Listed under CAS 252554-78-2, classified as non-hazardous with standard laboratory precautions.

Global Supplier: Pukang Biotechnology

Pukang Biotechnology supplies high-purity Fmoc-Ala-Ser(ψMe,Mepro)-OH (CAS 252554-78-2) alongside custom peptide synthesis services. Their offerings include:

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

• Technical Support: Optimization of ψPro integration for challenging sequences.

• Fast Global Shipping: Ensuring uninterrupted research and production timelines.

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

Conclusion

Fmoc-Ala-Ser(ψMe,Mepro)-OH (CAS 252554-78-2) is a transformative tool for peptide chemists, addressing aggregation and solubility challenges in SPPS. Its pseudoproline technology enables efficient synthesis of therapeutic peptides, structural biology probes, and high-purity vaccine components. For researchers targeting complex peptide-d therapeutics, CAS 252554-78-2 offers a robust solution to enhance synthesis success rates and accelerate drug discovery.