25691-37-6
Chemical Structure
Boc-L-2,4-Diaminobutyric acid
Synonym(s): N-Boc-L-2,4-diaminobutyric acid; Boc-Dab-OH
- CAS No.: 25691-37-6
- Formula:C9H18N2O4
- Molecular Weight:218.25
IUPAC Name: (S)-4-amino-2-((tert-butoxycarbonyl)amino)butanoic acid
InChIKey: MDCPCLPRWLKUIQ-LURJTMIESA-N
SMILES: O=C(O)[C@@H](NC(OC(C)(C)C)=O)CCN
Biological Activity: Boc-L-2,4-Diaminobutyric acid (N-Boc-L-2,4-diaminobutyric acid; Boc-Dab-OH) is a versatile synthetic starting material with a cleavable protecting group. Boc-L-2,4-Diaminobutyric acid not only reduces the backbone cleavage rate by protecting the side-chain γ-amino group, but also triggers intramolecular cyclization of self-immolative linkers under acidic cleavage conditions, thus constructing stimuli-responsive materials. Boc-L-2,4-Diaminobutyric acid is also an important building block for bioactive molecules. It can be used in the synthesis of ASCT2 (SLC1A5) inhibitors and carboxynorspermine, and can also serve as an internal standard to support the quantitative detection of specific intracellular amino acids by UPLC-QQQ-MS[1][2][3][4].
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Boc-L-2,4-Diaminobutyric acid | 98.0% | Boc-L-2,4-Diaminobutyric acid (N-Boc-L-2,4-diaminobutyric acid; Boc-Dab-OH) is a versatile synthetic starting material with a cleavable protecting group. Boc-L-2,4-Diaminobutyric acid not only reduces the backbone cleavage rate by protecting the side-chain γ-amino group, but also triggers intramolecular cyclization of self-immolative linkers under acidic cleavage conditions, thus constructing stimuli-responsive materials. Boc-L-2,4-Diaminobutyric acid is also an important building block for bioactive molecules. It can be used in the synthesis of ASCT2 (SLC1A5) inhibitors and carboxynorspermine, and can also serve as an internal standard to support the quantitative detection of specific intracellular amino acids by UPLC-QQQ-MS. | ||||||||||||||||||||
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- [1]. Mejia J S, et al. Triggered degradation of poly (ester amide) s via cyclization of pendant functional groups of amino acid monomers[J]. Polymer Chemistry, 2013, 4(6): 1969-1982.
- [2]. Schulte ML, et al. 2-Amino-4-bis(aryloxybenzyl)aminobutanoic acids: A novel scaffold for inhibition of ASCT2-mediated glutamine transport. Bioorg Med Chem Lett. 2016;26(3):1044-1047. [Content Brief]
- [3]. Lee J, et al. An alternative polyamine biosynthetic pathway is widespread in bacteria and essential for biofilm formation in Vibrio cholerae. J Biol Chem. 2009;284(15):9899-9907. [Content Brief]
- [4]. Zhou BJ, et al. Real-Time Tracking of ASCT2-Mediated Glutamine Uptake in Living Tumors With a Bioorthogonal Bioluminescent Probe. Adv Sci (Weinh). 2025;12(40):e07057. [Content Brief]
Keywords
