(2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate
[CAS# 823202-99-9]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other protected amino acids
• Name: (2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate
• Synonyms: Dipeptide diaminobutyroyl benzylamide diacetate; Acetic acid (2S)-N-[(2S)-4-amino-1-(benzylamino)-1-oxobutan-2-yl]-1-(3-aminopropanoyl)pyrrolidine-2-carboxamide
• Molecular Formula: C₁₉H₂₉N₅O₃.2(C₂H₄O₂)
• Molecular Weight: 495.58
• Protein Sequence: XPX
• CAS Registry Number: 823202-99-9
• EC Number: 676-431-9
• SMILES: CC(=O)O.CC(=O)O.C1C[C@H](N(C1)C(=O)CCN)C(=O)N[C@@H](CCN)C(=O)NCC2=CC=CC=C2

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H311
• Safety Statements: P262-P264-P270-P280-P302+P352-P316-P321-P361+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H311

Discovery and Applications

(2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate, a dipeptide derivative, has garnered significant attention in biochemistry and medicinal chemistry due to its structural versatility and potential bioactivity. Its discovery and applications reflect ongoing advancements in peptide synthesis and their therapeutic use.

This compound was first synthesized during research efforts aimed at creating modified dipeptides with enhanced stability and biological activity. Incorporating amino acids such as beta-alanine and proline into its structure provides a unique framework for potential interaction with biological targets. The phenylmethyl group in the structure adds hydrophobic character, while the acetate form enhances its solubility and stability.

The synthesis of (2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate involves sequential coupling reactions using protected amino acid derivatives. Standard peptide coupling methods, such as those employing carbodiimides or phosphonium-based reagents, are employed to achieve high yields and purity. Advances in solid-phase peptide synthesis have further streamlined its production, enabling the creation of analogs for structure-activity relationship studies.

Applications of this compound extend to therapeutic research, particularly in areas such as enzyme inhibition, receptor modulation, and as a precursor for drug design. Its dipeptide backbone mimics natural substrates, allowing it to act as a competitive inhibitor or modulator in enzymatic reactions. Additionally, the phenylmethyl moiety may enhance binding affinity to target sites, making it a candidate for studying ligand-receptor interactions.

In pharmaceutical development, derivatives of this compound are being explored for their potential in treating metabolic disorders, inflammatory conditions, and certain infectious diseases. Its ability to be modified at various positions makes it a versatile scaffold for medicinal chemists aiming to enhance potency, selectivity, and pharmacokinetic properties.

The acetate salt of the compound offers improved handling and storage, making it suitable for formulation studies. It also exhibits promising solubility in aqueous environments, a critical factor in drug development. Current research focuses on optimizing its bioavailability and understanding its metabolic pathways to minimize potential side effects.

Overall, (2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate represents a valuable tool in biochemical research and drug discovery. Its unique structural attributes and potential applications ensure that it remains an important focus for future scientific exploration.

References

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