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Home >> Chemical Listing >> A >> (2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate

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

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Complete supplier list of (2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate
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 Structure CAS # 823202-99-9, (2S)-beta-Alanyl-L-prolyl-2,4-diamino-N-(phenylmethyl)butanamide acetate, Dipeptide diaminobutyroyl benzylamide diacetate, Acetic acid (2S)-N-[(2S)-4-amino-1-(benzylamino)-1-oxobutan-2-yl]-1-(3-aminopropanoyl)pyrrolidine-2-carboxamide
Protein Sequence XPX
Molecular Formula C19H29N5O3.2(C2H4O2)
Molecular Weight 495.58
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 symbol   GHS06 Danger    Details
Hazard Statements H311    Details
Precautionary Statements P262-P264-P270-P280-P302+P352-P316-P321-P361+P364-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.3H311
SDS Available
up Discovory and Applicatios
(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

2018. Extreme cosmetics and borderline products: an analytical-based survey of European regulation compliance. Analytical and Bioanalytical Chemistry, 410(27).
DOI: 10.1007/s00216-018-1312-3

2016. Viper Venom Botox: The Molecular Origin and Evolution of the Waglerin Peptides Used in Anti-Wrinkle Skin Cream. Journal of Molecular Evolution, 83(5-6).
DOI: 10.1007/s00239-016-9764-6

2020. Cosmeceuticals. Practical Introduction to Laser Dermatology.
DOI: 10.1007/978-3-030-46451-6_10
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