In the intricate world of peptide synthesis and organic chemistry, understanding the precise chemical properties of building blocks is fundamental for successful research and development. Fmoc-Dab(Alloc)-OH, chemically known as Nα-Fmoc-Nγ-Alloc-L-2,4-diaminobutyric acid (CAS 204316-32-5), stands out as a particularly versatile and valuable reagent. This deep dive explores its chemistry, protecting group strategies, and its significance for R&D scientists.

At its core, Fmoc-Dab(Alloc)-OH is a derivative of 2,4-diaminobutyric acid, an unnatural amino acid that offers a unique spacing between its two amino groups. This structure is exploited in peptide synthesis to introduce specific functionalities or conformational constraints. The protection strategy employed here is key: the alpha-amino group is protected by the widely used Fmoc (9-fluorenylmethyloxycarbonyl) group, while the epsilon-amino group is protected by the Alloc (allyloxycarbonyl) group.

The Fmoc group is the workhorse of modern SPPS. Its removal is readily achieved under mild basic conditions, typically using a solution of piperidine (e.g., 20% in DMF). This deprotection step regenerates the free alpha-amino group, which is then activated and coupled to the next amino acid in the growing peptide chain. The efficiency and mildness of Fmoc deprotection are critical for maintaining the integrity of sensitive peptide sequences.

The Alloc group, positioned on the gamma-amino nitrogen of the diaminobutyric acid side chain, offers a complementary protection strategy. Its defining feature is its orthogonality to Fmoc chemistry. This means it can be selectively removed using palladium(0) catalysis, often in the presence of a scavenger like tributyltin hydride or an allyl scavenger. This selective deprotection is invaluable for:

  • Site-Specific Modifications: Allowing functionalization of the side-chain amino group while the peptide is still attached to the resin or after it has been cleaved.
  • Peptide Conjugation: Facilitating the attachment of peptides to other molecules, such as polymers, surfaces, or cytotoxic drugs, for applications in drug delivery or diagnostics.
  • Introducing Unique Structures: Enabling the synthesis of branched peptides, cyclic peptides, or peptidomimetics that leverage the diaminobutyric acid scaffold.

For R&D scientists, sourcing high-quality Fmoc-Dab(Alloc)-OH is paramount. When you 'buy Fmoc-Dab(Alloc)-OH', you should look for suppliers who provide comprehensive analytical data, including NMR, HPLC, and MS, to confirm purity and structure. NINGBO INNO PHARMCHEM CO.,LTD., as a premier 'Fmoc-amino acid supplier' and 'manufacturer in China', ensures that our Fmoc-Dab(Alloc)-OH meets rigorous standards. We offer competitive pricing and reliable access to this vital reagent. If you are searching for 'Fmoc-Dab(Alloc)-OH price' or need to 'purchase Fmoc-Dab(Alloc)-OH' for your next project, we are your trusted partner.