In the intricate world of organic chemistry and particularly in peptide synthesis, understanding the precise structure and reactivity of building blocks is crucial. N-alpha-Fmoc-D-Aspartic acid alpha-tert-butyl ester (CAS 134098-70-7), commonly known as Fmoc-D-Asp-OtBu, is one such indispensable molecule. This article explores its chemical structure, synthesis, and diverse applications that make it a sought-after intermediate for chemists worldwide.

Unpacking the Chemical Structure: Fmoc-D-Asp-OtBu

The systematic name, N-alpha-Fmoc-D-Aspartic acid alpha-tert-butyl ester, breaks down its key features:

  • Aspartic Acid: This is a naturally occurring acidic amino acid. The 'D' signifies that it is the D-enantiomer, a stereoisomer that differs in its spatial arrangement compared to the more common L-enantiomer found in proteins.
  • N-alpha-Fmoc: The Fmoc group (9-fluorenylmethyloxycarbonyl) is attached to the alpha-amino group of the aspartic acid. This protecting group is essential for controlled sequential addition of amino acids during peptide synthesis. It is known for its lability under mild basic conditions, allowing for selective removal.
  • alpha-tert-butyl ester: The alpha-carboxyl group is esterified with a tert-butyl group. This bulky ester serves as a protecting group for the side-chain carboxyl functionality of aspartic acid. It is typically removed under acidic conditions, often alongside other acid-labile side-chain protecting groups.

The molecular formula for Fmoc-D-Asp-OtBu is C23H25NO6, with a molecular weight of approximately 411.45 g/mol. Its synthesis generally involves the selective protection of D-aspartic acid, first with the Fmoc group on the amine and then with the tert-butyl ester on the side-chain carboxyl group, or vice-versa, depending on the specific synthetic route chosen by the manufacturer.

Synthesis Applications and Advantages

The strategic combination of protecting groups makes Fmoc-D-Asp-OtBu an exceptionally useful building block:

  • Peptide Synthesis: Its primary application is in solid-phase and solution-phase peptide synthesis. The Fmoc group allows for easy coupling through activation of the free carboxyl group, while the tert-butyl ester protects the side chain. This controlled addition is vital for constructing complex peptide sequences accurately. Researchers often buy this compound to introduce a D-aspartic acid residue at specific positions within a peptide chain, which can influence folding, stability, and receptor interaction.
  • Drug Discovery and Development: As a component of peptide-based therapeutics, Fmoc-D-Asp-OtBu plays a role in creating molecules with targeted biological activity. Its incorporation can lead to peptides with altered pharmacokinetic profiles or enhanced efficacy.
  • Advanced Organic Synthesis: Beyond peptides, this protected amino acid can serve as a chiral synthon in the synthesis of other complex organic molecules, pharmaceuticals, or specialized fine chemicals where a chiral aspartic acid moiety is required.

When sourcing Fmoc-D-Asp-OtBu, it is imperative to obtain it from a reliable manufacturer that ensures high chemical purity and enantiomeric integrity. A quality supplier, like a dedicated manufacturer in China, can provide the necessary documentation and consistent product for your research and development needs. Understanding the chemical underpinnings of this reagent empowers chemists to leverage its full potential in creating advanced molecules.