Fmoc-Dab(Adpoc)-OH is an Fmoc-protected amino acid derivative featuring a substituted 2,4-diaminobutyric acid (Dab) backbone in which the side-chain amino functionality is masked as an Adpoc (1-adamantyl-based oxycarbonyl) protecting group, while the α-amino group is protected by the Fmoc carbamate. The molecule contains a free carboxylic acid (-COOH) and a carbamate-linked Fmoc group, with the Adpoc group providing chemoselective suppression of the side-chain amine's reactivity during stepwise assembly. This protected building block is used in peptide synthesis workflows to control orthogonal amine reactivity, enabling selective deprotection and subsequent coupling steps for preparing peptides and related amino acid conjugates bearing a protected Dab residue.
CAT No: CP26784
CAS No:214750-73-9
Synonyms/Alias:Fmoc-Dab(Adpoc)-OH;214750-73-9;6815AH;ZINC71788135
Fmoc-Dab(Adpoc)-OH is an Fmoc-protected amino acid derivative built on the Dab scaffold (2,3-diaminopropionic acid), bearing an Adpoc-protected side-chain amino group that is compatible with orthogonal deprotection strategies. The molecule contains an N-Fmoc carbamate for base-stable temporary protection during peptide assembly, along with a carboxylic acid handle for coupling as a C-terminal or side-chain functionalized building block. The Adpoc (adamantyl-based oxycarbonyl) group provides steric shielding and controlled stability, enabling selective unveiling of the additional amine for downstream conjugation or further derivatization. The defined stereochemical relationship of the Dab center supports stereocontrolled incorporation into peptide sequences and enables formation of predictable side-chain substitution patterns in synthetic and biochemical studies.
1. Peptide Synthesis
Fmoc-Dab(Adpoc)-OH serves as a protected peptide building block for solid-phase peptide synthesis and solution-phase coupling workflows where a diamino side chain is required. The N-terminal Fmoc carbamate supports standard peptide coupling chemistry while the carboxylic acid enables formation of amide bonds under peptide synthesis conditions. The Adpoc-protected side-chain amine remains masked during chain elongation, reducing side reactions such as premature crosslinking or uncontrolled branching. After selective deprotection, the revealed side-chain amine can be used to generate peptide variants with controlled charge density and branching, supporting construction of Dab-containing sequences for peptide science and peptidomimetic libraries.
2. Side-Chain Functionalization
Fmoc-Dab(Adpoc)-OH supports amino acid derivatization workflows targeting controlled installation of functional groups onto the additional Dab amine. The Adpoc group provides a protecting-group platform that can be removed to expose a primary amine for subsequent acylation, alkylation, sulfonylation, or formation of urea and amide linkages. The resulting derivatives can be engineered to tune solubility, hydrogen-bonding patterns, and intramolecular interactions while maintaining the protected peptide-ready backbone during intermediate stages. Downstream functionalized products can be used as chemical biology reagents, scaffold intermediates, or charged-linker components in larger conjugation schemes.
3. Bioconjugation Chemistry
Fmoc-Dab(Adpoc)-OH is suitable for bioconjugation development where orthogonally protected amines enable stepwise attachment to biomolecules. The masked side-chain amine helps maintain chemoselectivity during preparation of peptide conjugates, affinity ligands, or linker-bearing constructs, while the Fmoc group allows controlled exposure of the N-terminus during assembly. After deprotection, the free primary amine can participate in coupling reactions to introduce handles for fluorescent labeling, affinity tags, or immobilization on activated surfaces. The amino acid-based linker architecture supports formation of stable amide or related nitrogen-containing linkages that remain compatible with downstream analytical characterization and process-scale conjugate manufacturing.
4. Protected Amino Acid Intermediate
Fmoc-Dab(Adpoc)-OH functions as a chiral amino acid intermediate for protected amino acid synthesis and orthogonal protection design in synthetic organic chemistry. The combination of an Fmoc-protected N-terminus with an Adpoc-protected side-chain amine provides a two-site protection scheme that can be selectively manipulated to control which nitrogen participates at each stage. The carboxylic acid enables conversion into activated coupling forms for incorporation into larger fragments, while the protected amine supports iterative derivatization without uncontrolled oligomerization. This intermediate utility aligns with fine chemical synthesis needs for preparing Dab-containing fragments, protected peptide analogs, and stereochemically defined building blocks used in both research workflows and industrial intermediate preparation.
5. Process Chemistry Manufacturing
Fmoc-Dab(Adpoc)-OH can be employed in process chemistry for manufacturing of protected peptide intermediates and industrial-scale fine chemicals requiring robust protection-group handling. The Fmoc carbamate is designed for predictable base-mediated removal during peptide processing, while the Adpoc group can withstand conditions used during upstream transformations, supporting controlled sequencing of protection and deprotection steps. The presence of a single carboxylic acid functionality facilitates conversion to coupling-ready derivatives and integration into automated or semi-automated synthesis platforms. The resulting manufacturing route compatibility supports reliable generation of Dab-containing peptide building blocks, peptidomimetic precursors, and nitrogen-functionalized intermediates for specialty chemical production and downstream polymer- or surface-functionalization programs where amine-bearing linkers are required.
6. Analytical Research Standards
Fmoc-Dab(Adpoc)-OH is applicable to analytical research as a defined protected amino acid standard for method development and characterization of Dab-containing peptide products. The Fmoc group and Adpoc-protected side chain provide distinct mass and fragmentation signatures that can assist in LC-MS or MS/MS identification of intermediates and partially deprotected species. The molecule's carboxylic acid and protected amines support preparation of reference materials used to verify coupling completeness, monitor protecting-group stability, and confirm deprotection selectivity. Analytical use of this chiral amino acid derivative can extend to quality control workflows for peptide building block integrity, supporting reproducible interpretation of peptide synthesis and functionalization outcomes.
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