New Edition,α,γ-diaminobutyric acid

The realm of peptide chemistry is continuously expanding, introducing novel building blocks that enhance the capabilities of synthetic peptides. Among these, DAB peptide, specifically referring to peptides incorporating 2,4-Diaminobutyric Acid (DAB), has emerged as a significant area of research and development. This non-proteinogenic amino acid offers unique structural and functional advantages, making it a valuable component in the creation of advanced peptides for various applications.

Understanding 2,4-Diaminobutyric Acid (DAB)

2,4-Diaminobutyric acid (DAB) is a fascinating non-proteinogenic diamino acid that has garnered significant attention in peptide chemistry. Unlike the 20 standard amino acids found in proteins, DAB is a diamino acid of low molecular weight and is not incorporated during ribosomal protein synthesis. It can exist in different stereochemical forms, with the S-form, L-2,4-diaminobutyric acid, being the most frequently encountered. The structure of DAB features amino groups at both the alpha (α) and gamma (γ) positions, distinguishing it from other common amino acids. This unique di-functional nature is key to its utility in peptide synthesis.

The Role of DAB in Peptide Synthesis and Design

The incorporation of DAB into peptide sequences offers several key advantages. Peptides incorporating D- and unnatural amino acids, including DAB, have demonstrated enhanced stability towards proteases. This increased stability is crucial for therapeutic peptides, as it can prolong their half-life in biological systems. Furthermore, the introduction of DAB can influence the overall amphipathic nature of a peptide, impacting its interaction with cell membranes and other biological targets.

For scientists and procurement specialists aiming for precise peptide assembly, Fmoc-D-Dab(Boc)-OH stands out as a vital protected amino acid derivative. This protected form of DAB is a cornerstone for custom peptide synthesis. The Fmoc (9-fluorenylmethyloxycarbonyl) group serves as a widely used protecting group for the alpha-amino function, while the Boc (tert-butyloxycarbonyl) group typically protects the gamma-amino group. Other protecting group strategies, such as the use of N-Allyloxycarbonyl (Alloc) groups, are also employed for specific synthetic needs, as they are rapidly and quantitatively converted to free amines.

The availability of various protected forms, including Fmoc-D-Dab(Boc)-OH with CAS No. 114360-56-4 and Fmoc-Dab(Boc)-OH (CAS 125238-99-5), underscores the importance of DAB in the field. These reagents, often available in pack sizes of 1g and 5g, facilitate researchers in their work. The molecular weight of Fmoc-Dab(Boc)-OH is approximately 440.49 g/mol, with the empirical formula C24H28N2O. Similarly, Fmoc-Dab(Ac)-OH has a molecular weight of 382.38 g/mol and the formula C21H22N2O5.

Applications and Emerging Research

The unique properties of DAB peptide have led to their exploration in diverse applications. Research has shown that substituting standard amino acids like Arginine (Arg) and Lysine (Lys) with DAB or Dap (diaminopropane) can significantly alter the lytic activity of antimicrobial peptides against human red blood cells. This highlights the potential for fine-tuning peptide efficacy and specificity through the strategic incorporation of DAB.

Beyond antimicrobial applications, DAB plays a role in the development of more complex peptide structures. The ability to orthogonally protect the two amino groups allows for the synthesis of cyclic and branched peptides, further expanding the repertoire of peptide designs. Companies like P3 BioSystems and PeptART Bioscience GmbH offer high quality peptides and peptide synthesis reagents, including various Dab & Dap derivatives, catering to the growing demand for these specialized building blocks.

While some sources may refer to DAB as a nonproteinaceous diamino acid of low molecular weight, its significance in modern chemistry and biology is undeniable. The exploration into DAB peptide continues, with ongoing research investigating its potential in areas such as drug development, including the creation of PD-L1 inhibitory peptide constructs. The availability of these specialized amino acids, often accompanied by detailed product specifications and competitive pricing, ranging from CHF 337.10 – CHF 1,349.30 for certain quantities, enables continued innovation in the field.

In conclusion, DAB peptide represents a powerful advancement in peptide chemistry. The versatility of 2,4-Diaminobutyric acid (DAB), coupled with the availability of sophisticated protecting group strategies and a growing array of derivatives like Fmoc-D-Dab(Boc)-OH and Fmoc-Dab(Boc)-OH, empowers researchers to design and synthesize peptides with enhanced properties and novel functionalities