2,3-Diaminopropionic acid is an amino acid that is a precursor of antibiotics and a siderophore[1]. The β-amino group of 2,3-Diaminopropionic acid acts as a nucleophile and forms amide bonds with the substrates of enzymes, which enables the trapping of acyl-enzyme intermediates that are linked through an amide bond[2]. 2,3-Diaminopropionic acid can be used as a building block to shift the backbone of the cathelicidin LL-37, thereby altering the function and enhancing the enzymatic stability[3]. 2,3-Diaminopropionic acid carries a positive charge under the weakly acidic pH conditions of tumor tissues, while remaining neutral at physiological pH 7.4, and this pH-dependent charge property endows 2,3-diaminopropionic acid with significant potential for application in the preparation of anticancer peptides and pH-sensitive drug delivery carriers[4-5].
References:
[1] Kobylarz M J, Grigg J C, Shin-ichi J T, et al. Synthesis of L-2, 3-diaminopropionic acid, a siderophore and antibiotic precursor[J]. Chemistry & biology, 2014, 21(3): 379-388.
[2] Huguenin-Dezot N, Alonzo D A, Heberlig G W, et al. Trapping biosynthetic acyl-enzyme intermediates with encoded 2, 3-diaminopropionic acid[J]. Nature, 2019, 565(7737): 112-117.
[3] Rejmak W, Bury K, Bauer M, et al. Building Blocks of 2, 3-Diaminopropionic Acid Functionalized with an Oxa-Acid Spacer Shift the Functional Profile of Human Cathelicidin LL-37: Enhanced Enzymatic Stability and Selective Suppression of Neutrophil Degranulation[J]. Pharmaceuticals, 2026, 19(8): 1152.
[4] Lan Y, Langlet‐Bertin B, Abbate V, et al. Incorporation of 2, 3‐diaminopropionic acid into linear cationic amphipathic peptides produces pH‐sensitive vectors[J]. ChemBioChem, 2010, 11(9): 1266-1272.
[5] Tanishiki N, Yano Y, Matsuzaki K. Endowment of pH responsivity to anticancer peptides by introducing 2, 3‐diaminopropionic acid residues[J]. ChemBioChem, 2019, 20(16): 2109-2117.