N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine is a protected dipeptide that facilitates controlled coupling and orthogonal deprotection. The Boc-like protection modulates N-terminal reactivity. Researchers evaluate its stability and performance in SPPS workflows. Applications include method optimization, backbone construction, and protected-fragment insertion.
CAT No: R2361
CAS No:27317-69-7
Synonyms/Alias:N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine;BOC-ALA-ALA-OH;27317-69-7;(tert-Butoxycarbonyl)-L-alanyl-L-alanine;Boc-L-Ala-L-ala;MFCD00038564;N-Boc-L-alanyl-L-alanine;boc-l-alanyl-l-alanine;N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine;N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-L-alanine;L-Alanine, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-;NSC 334362;boc-alanyl-alanine;NSC 334362; N-tert-ButoxycarbonylalanylalanineTert-Butoxycarbonyl-L-alanyl-L-alanine; N-Boc-L-alanyl-L-alanine;Boc-(Ala)2-OH;Boc-Ala-Ala-OH, AldrichCPR;(S)-2-((S)-2-(tert-butoxycarbonylamino)propanamido)propanoic acid;SCHEMBL6891888;CHEMBL2371142;DTXSID40950035;BZNDDHWTEVCBAD-BQBZGAKWSA-N;AKOS027340118;FB48198;HY-W039756;s12086;DS-12425;N-tert-butyloxycarbonyl-L-alanyl-L-alanine;N-(tert-Butoxycarbonyl)-L-alanyl-L-alanine;B6187;CS-0097837;NS00004174;
N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine, also known as Boc-Ala-Ala-OH, is a dipeptide derivative widely recognized for its utility in peptide synthesis and organic chemistry research. Featuring a tert-butoxycarbonyl (Boc) protecting group at the N-terminus, this compound offers enhanced stability and selectivity during peptide bond formation, making it a favored intermediate for constructing more complex peptide chains. Its well-defined structure and compatibility with a variety of coupling reagents allow chemists to manipulate and extend peptide sequences with high fidelity. The presence of the Boc group ensures that undesired side reactions at the amino terminus are minimized, facilitating efficient synthetic strategies in the laboratory. As a result, N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine is a valuable building block in research settings focused on peptide design, modification, and functionalization.
Peptide Synthesis: Boc-Ala-Ala-OH is extensively utilized as a protected dipeptide in solid-phase and solution-phase peptide synthesis protocols. Its Boc-protected N-terminus enables sequential addition of amino acids without unwanted reactions at the amino group, while the free carboxyl group at the C-terminus allows for straightforward coupling to other amino acids or peptide fragments. This makes it an essential intermediate for assembling oligopeptides and polypeptides, aiding researchers in constructing tailored peptide libraries for various biochemical and structural studies. The compound's reactivity profile is well-suited for use with common peptide coupling reagents such as carbodiimides and uronium salts, ensuring compatibility with automated synthesizers and manual protocols alike.
Pharmaceutical Research: In the context of pharmaceutical development, N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine serves as a model compound for studying peptide stability, enzymatic hydrolysis, and drug delivery mechanisms. Its defined structure allows researchers to investigate the behavior of dipeptide motifs within larger therapeutic candidates, providing insights into metabolism, transport, and degradation pathways. Additionally, it can be incorporated into prodrug strategies, where the peptide moiety modulates the pharmacokinetic properties of active pharmaceutical agents, thereby contributing to the rational design of novel drug candidates.
Enzyme Substrate Studies: As a substrate analog, Boc-Ala-Ala-OH is employed in enzymology to probe the specificity and catalytic mechanisms of proteases and peptidases. By introducing this dipeptide into enzymatic assays, researchers can assess how modifications to peptide backbones influence substrate recognition and turnover rates. Such studies are instrumental in elucidating enzyme function, guiding the development of selective inhibitors, and advancing our understanding of proteolytic pathways in biological systems.
Proteomics and Analytical Chemistry: The compound finds application in proteomics as a standard or reference material for method development and validation in peptide analysis. Its defined molecular structure and predictable chromatographic behavior make it suitable for calibrating liquid chromatography-mass spectrometry (LC-MS) instruments and optimizing sample preparation protocols. By serving as a model peptide, it assists in troubleshooting analytical workflows and ensuring reproducibility in peptide quantification experiments.
Biomaterials Research: In the field of biomaterials, Boc-Ala-Ala-OH is incorporated into the design and synthesis of peptide-based hydrogels, coatings, and scaffolds. Its modular structure enables the creation of functionalized materials with tunable mechanical and biochemical properties, supporting the development of advanced platforms for cell culture, tissue engineering, and regenerative medicine research. The dipeptide can be strategically modified or extended to introduce bioactive motifs that promote cell adhesion, proliferation, or differentiation, thus expanding the versatility of peptide-derived biomaterials.
Synthetic versatility, reliable protection, and compatibility with modern research techniques make N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine indispensable in contemporary chemical and biochemical laboratories. Whether facilitating the stepwise assembly of complex peptides, supporting pharmaceutical innovation, enabling detailed enzyme studies, enhancing analytical methods, or driving advances in biomaterials, this dipeptide derivative provides a robust foundation for scientific exploration. Its widespread adoption across multiple disciplines underscores its importance as a foundational tool for researchers seeking to unlock the potential of peptide chemistry and its diverse applications.
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