2,4-Diaminobutyric acid

vanc 6 2,4-Diaminobutyric acid.svg 2-4-Diaminobutyric-acid Conformer3D large.png 2,4-Diaminobutanoic acid α,γ-diaminobutanoic acid 305-62-4 correct CAS 64307 307931 457 206-166-2 470 92V7KM11ZK C(CN)C(C(=O)O)N 1S/C4H10N2O2/c5-2-1-3(6)4(7)8/h3H,1-2,5-6H2,(H,7,8) OGNSCSPNOLGXSM-UHFFFAOYSA-N 4 10 2 2 GABA-T inhibitor; GABA reuptake inhibitor 2,4-Diaminobutyric acid, also known as DABA, is GABA-T non-competitive inhibitor and a GABA reuptake inhibitor. In many bacteria, its (S) enantiomer is a natural product which is an intermediate to the osmoprotectant, ectoine. Mechanism of action DABA's main action is being an inhibitor of GABA transaminase, an enzyme that converts GABA back to glutamate. When the enzyme is inhibited, this conversion cannot happen, therefore, GABA levels are elevated. Beart PM, Bilal K l-2,4-Diaminobutyric acid and the GABA system Neuroscience Letters 5 3–4 193–198 July 1977 19604993 10.1016/0304-3940(77)90046-5 34289803 It has also been observed that 2,4-diaminobutyric acid is a GABA reuptake inhibitor. Taberner PV, Pycock CJ The Effects of GABA Uptake Inhibitors including 2, 4-Diaminobutyric Acid on GABA Metabolism in vivo https://link.springer.com/chapter/10.1007/978-1-4615-9778-0_12 10.1007/978-1-4615-9778-0_12 Pycock CJ, Taberner PV Central Neurotransmitter Turnover 1981 177–182 978-1-4615-9780-3 This action further elevates levels of GABA. Toxicity In addition to being a neurotoxin, DABA can also cause liver damage. Its potential as an anticonvulsant is unclear, it has been shown to have anticonvulsant properties against picrotoxin, but over the long term, it could paradoxically cause convulsions. O'Neal RM, Chen CH, Reynolds CS, Meghal SK, Koeppe RE The 'neurotoxicity' of L-2,4-diaminobutyric acid The Biochemical Journal 106 3 699–706 February 1968 5639925 1198561 10.1042/bj1060699 Biosynthesis and metabolism The (S) enantiomer of DABA is a natural product which is an intermediate in many bacteria to the osmoprotectant, ectoine. It is produced by the enzyme diaminobutyrate-2-oxoglutarate transaminase that produces it from L-aspartic-4-semialdehyde and glutamic acid. Peters P, Galinski EA, Truper HG 1990 The biosynthesis of ectoine FEMS Microbiol. Lett. 71 1–2 157–162 10.1111/j.1574-6968.1990.tb03815.x free It has been found in Halomonas elongata and Bacillus pasteurii. Ono H, Sawada K, Khunajakr N etal 1999 Characterization of biosynthetic enzymes for ectoine as a compatible solute in a moderately halophilic eubacterium, Halomonas elongata J. Bacteriol. 181 91–9 9864317 1 10.1128/JB.181.1.91-99.1999 103536 Kuhlmann AU, Bremer E 2002 Osmotically regulated synthesis of the compatible solute ectoine in Bacillus pasteurii and related Bacillus spp Appl. Environ. Microbiol. 68 772–83 11823218 10.1128/AEM.68.2.772-783.2002 2 126723 2002ApEnM..68..772K 75% L-Aspartic-4-semialdehyde + Q26995161 Glutamic acid Q27094699 2,4-Diaminobutyric acid + α-Ketoglutaric acid In other organisms including Acinetobacter baumannii and Haemophilus influenzae, DABA is the precursor to 1,3-diaminopropane. Ikai H, Yamamoto S 1997 Identification and analysis of a gene encoding L-2,4-diaminobutyrate:2-ketoglutarate 4-aminotransferase involved in the 1,3-diaminopropane production pathway in Acinetobacter baumannii J. Bacteriol. 179 5118–25 9260954 16 179370 10.1128/jb.179.16.5118-5125.1997 Ikai H, Yamamoto S 1998 Two genes involved in the 1,3-diaminopropane production pathway in Haemophilus influenzae Biol. Pharm. Bull. 21 170–3 9514614 2 10.1248/bpb.21.170 free References Category:GABA reuptake inhibitors Category:GABA transaminase inhibitors Category:Basic amino acids Category:Diamines