N-α-Fmoc-N-γ-allyloxycarbonyl-D-2,4-diaminobutyric acid is a protected, non-proteinogenic amino acid derivative featuring a 2,4-diaminobutyric acid backbone with an N-α Fmoc group and an N-γ allyloxycarbonyl (Alloc) protecting group. The molecule contains two amino functionalities (α-amino and a side-chain amino) and a carboxyl group, with the D stereochemical configuration indicated in the product name. In peptide chemistry and chemical biology workflows, the orthogonally protected amines provide chemoselective handles for stepwise assembly or modification of amino-acid-containing constructs, while the Fmoc and Alloc groups support controlled protection/deprotection strategies during synthesis and subsequent derivatization.
CAT No: CP05321
N-α-Fmoc-N-γ-allyloxycarbonyl-D-2,4-diaminobutyric acid is an Fmoc-protected D-configured diamino acid derivative featuring two stereochemically relevant amino functionalities along a short aliphatic backbone. The α-amino group is masked as an N-Fmoc carbamate to control peptide coupling at the N-terminus, while the γ-amino group is protected as an allyloxycarbonyl (Alloc) carbamate that can be selectively removed under orthogonal conditions. The molecule also bears a free carboxylic acid, enabling conversion to activated esters or coupling-ready forms for peptide building block preparation. The combination of orthogonal N-protecting groups and a D-configuration supports controlled sequential deprotection and incorporation into peptides, as well as downstream derivatization of the second amino site for side-chain functionalization and synthetic intermediate construction.
1. Peptide Synthesis
N-α-Fmoc-N-γ-allyloxycarbonyl-D-2,4-diaminobutyric acid is used in solid-phase and solution-phase peptide synthesis where orthogonal N-protection is required for diamino acid incorporation. The Fmoc carbamate on the α-amino group supports standard N-terminal deprotection and peptide coupling cycles, while the Alloc-protected γ-amino group remains masked during chain assembly. The free carboxylic acid functionality enables formation of peptide bonds through activation strategies compatible with common coupling chemistries, and the short 2,4-diaminobutyric framework can introduce constrained cationic motifs into peptide sequences. Selective Alloc removal after chain elongation can generate a reactive second amine for subsequent coupling, branching, or conjugation steps, supporting peptide analog construction and amino acid chemistry workflows.
2. Side-Chain Functionalization
N-α-Fmoc-N-γ-allyloxycarbonyl-D-2,4-diaminobutyric acid serves as a protected side-chain building block for introducing orthogonally unmasked amine handles in synthetic organic chemistry. The γ-Alloc carbamate provides a protected nucleophile that can be deprotected to reveal an amine for derivatization with acyl, sulfonyl, carbamoyl, or heteroatom-containing substituents. The D-configuration and diamino spacing can influence intramolecular conformations and the positioning of cationic groups, which is relevant when building peptidomimetics or charge-modified scaffolds. Downstream functionalization of the revealed γ-amine supports generation of labeled peptides, affinity reagents, and chemically defined intermediates for further synthesis, aligning with amino acid derivatization and protected amino acid chemistry strategies.
3. Chemical Biology Conjugation
N-α-Fmoc-N-γ-allyloxycarbonyl-D-2,4-diaminobutyric acid is applied in chemical biology workflows that require controlled introduction of additional amine functionality for biomolecule modification. The orthogonal Fmoc/Alloc protection pattern enables stepwise exposure of amino groups, allowing selective conjugation to electrophiles such as activated esters, isothiocyanates, haloacetamides, or aldehyde-derived linkers after peptide or scaffold assembly. The presence of a carboxylic acid and two protected amines supports preparation of defined conjugation-ready intermediates, including peptide conjugates and amine-rich molecular probes. The D-2,4-diaminobutyric motif can also be used to tune charge density and binding-site presentation in synthetic constructs used for target engagement studies and molecular recognition experiments.
4. Process Chemistry Intermediate
N-α-Fmoc-N-γ-allyloxycarbonyl-D-2,4-diaminobutyric acid is suitable for industrial and process chemistry contexts where orthogonally protected amino acid derivatives are manufactured as repeatable intermediates. The Fmoc carbamate and Alloc carbamate provide chemically stable protecting-group architectures during handling and upstream synthesis, while still enabling predictable downstream deprotection sequences for manufacturing route design. The free carboxylic acid allows conversion to coupling reagents or activated forms that can be integrated into scalable peptide-building operations and fine chemical synthesis plans. The diamino acid structure supports production of downstream protected peptide fragments and functionalized amino acid intermediates for specialty chemical production, including workflows that depend on controlled amine availability and stereochemically defined inputs.
5. Analytical Research Standards
N-α-Fmoc-N-γ-allyloxycarbonyl-D-2,4-diaminobutyric acid is used in analytical research as a stereochemically defined reference material for monitoring amino acid derivatization, protecting-group integrity, and peptide coupling performance. The orthogonal Fmoc and Alloc carbamates create characteristic mass and fragmentation signatures that can be leveraged in LC-MS, HPLC, and MS/MS method development for protected amino acid synthesis and peptide intermediate characterization. The D-configuration and diamino functionality support calibration of assays that distinguish stereoisomeric or partially deprotected species during synthesis and purification. The compound can also serve as a starting material for preparing labeled or derivatized analytical standards that reflect downstream structures encountered in peptide science and amino acid chemistry, supporting robust method transfer across research and manufacturing environments.
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