Nα-Fmoc-Nγ-Alloc-L-2,4-diaminobutyric acid, or Fmoc-Dab(Alloc)-OH (CAS 204316-32-5), is a highly specialized amino acid derivative widely utilized in modern peptide chemistry. Its unique structural features, combining the Fmoc protecting group on the alpha-amino nitrogen and the Alloc protecting group on the gamma-amino nitrogen, make it an exceptionally versatile building block for Solid-Phase Peptide Synthesis (SPPS) and other complex organic syntheses.

The chemical properties of Fmoc-Dab(Alloc)-OH are central to its utility. With a molecular formula of C23H24N2O6 and a molecular weight of approximately 424.45 g/mol, it typically appears as a white powder. The Fmoc group is designed for facile removal under mild basic conditions, usually with a solution of piperidine in an organic solvent. This deprotection step is a critical part of the iterative cycle in SPPS, freeing the alpha-amino group for reaction with the next activated amino acid.

The Alloc group provides orthogonal protection for the side-chain amino group. This means it can be removed selectively using conditions that do not affect the Fmoc group or the peptide backbone. Palladium(0) catalysis is the standard method for Alloc deprotection, generating an allyl-palladium complex and liberating carbon dioxide and diallyl ether. This orthogonal deprotection strategy is invaluable for introducing modifications or branching at the side chain of the diaminobutyric acid residue within a peptide sequence. Researchers often seek 'how to use Fmoc-Dab(Alloc)-OH' or 'Fmoc-Dab(Alloc)-OH applications' to understand its integration into their synthesis protocols.

The applications of Fmoc-Dab(Alloc)-OH span several critical research and development areas:

  • Peptide Synthesis: Its primary use is in constructing peptides with modified side chains or branching points, essential for peptidomimetics, cyclic peptides, and peptides with specific functionalization.
  • Drug Discovery: It serves as a key intermediate in the synthesis of peptide-based therapeutics, allowing for the fine-tuning of pharmacokinetic and pharmacodynamic properties.
  • Bioconjugation: The selectively cleavable Alloc group can be used for attaching peptides to other molecules, such as proteins, polymers, or surfaces, through click chemistry or other conjugation methods.
  • Research Reagents: As a high-purity Fmoc-amino acid, it is sought after by academic researchers and R&D departments for exploring novel chemical reactions and biological pathways.

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