The Chemical Profile of Fmoc-Dap(Alloc)-OH: Properties and Synthesis Implications
Fmoc-Dap(Alloc)-OH, identified by its CAS number 188970-92-5, is a sophisticated amino acid derivative that holds significant importance in modern synthetic chemistry, particularly in the field of peptide synthesis. Understanding its chemical profile—including its molecular formula, weight, and the strategic placement of protecting groups—is crucial for researchers aiming to leverage its capabilities in complex molecular construction.
The molecule's structure, C22H22N2O6, with a molecular weight of approximately 410.42 g/mol, is characterized by a central diaminopropionic acid backbone. The alpha-amino group is protected by the Fmoc (9-fluorenylmethyloxycarbonyl) moiety. This protecting group is highly favored in peptide synthesis due to its stability under acidic conditions and its facile cleavage using weak bases like piperidine. This selective deprotection allows for iterative addition of amino acids in a controlled manner during Solid Phase Peptide Synthesis (SPPS).
The beta-amino group is protected by the Alloc (allyloxycarbonyl) group. This is a particularly useful orthogonal protecting group. Orthogonality means that the Alloc group can be removed under conditions (typically using palladium catalysts) that do not affect the Fmoc group or other common side-chain protecting groups used in peptide synthesis. This feature enables chemists to selectively unmask the beta-amino group at a specific stage of synthesis for further functionalization, such as conjugation, cyclization, or the introduction of non-canonical amino acids.
The presence of these two distinct protecting groups on Fmoc-Dap(Alloc)-OH makes it a versatile building block for synthesizing peptides with complex architectures, including branched peptides, cyclic peptides, and peptidomimetics. Researchers often seek to buy this compound when designing synthetic strategies that require differential protection of amino groups. The ability to precisely control the sequence of deprotection and coupling steps is fundamental to achieving high yields and desired product purity.
For B2B buyers and research scientists, sourcing Fmoc-Dap(Alloc)-OH from reliable manufacturers or suppliers is paramount. Companies that specialize in amino acid derivatives and peptide synthesis reagents are the most likely sources. When evaluating these suppliers, it is important to consider not only the price but also the reported purity, analytical data (such as NMR and HPLC spectra), and the responsiveness of their customer service. Obtaining a detailed Certificate of Analysis (CoA) is standard practice for ensuring product quality.
The chemical properties of Fmoc-Dap(Alloc)-OH, such as its melting point (often in the range of 140-160°C, indicating it is a solid) and solubility, also play a role in its practical application. These details are typically available from the supplier and are important for optimizing reaction conditions. For any researcher or procurement manager looking to purchase this reagent, understanding these chemical nuances ensures efficient integration into synthesis workflows and contributes to the overall success of their projects.
Perspectives & Insights
Silicon Analyst 88
“This selective deprotection allows for iterative addition of amino acids in a controlled manner during Solid Phase Peptide Synthesis (SPPS).”
Quantum Seeker Pro
“Orthogonality means that the Alloc group can be removed under conditions (typically using palladium catalysts) that do not affect the Fmoc group or other common side-chain protecting groups used in peptide synthesis.”
Bio Reader 7
“This feature enables chemists to selectively unmask the beta-amino group at a specific stage of synthesis for further functionalization, such as conjugation, cyclization, or the introduction of non-canonical amino acids.”