2 aminoadipic acid

Summary

Summary: A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-METHYL-D-ASPARTATE; (NMDA).

Top Publications

  1. Kaczorowska M, Kmiec T, Jakobs C, Kacinski M, Kroczka S, Salomons G, et al. Pyridoxine-dependent seizures caused by alpha amino adipic semialdehyde dehydrogenase deficiency: the first polish case with confirmed biochemical and molecular pathology. J Child Neurol. 2008;23:1455-9 pubmed publisher
    ..Due to the availability of reliable laboratory testing, confirmation of the diagnosis was made without the life-threatening trial of pyridoxine withdrawal...
  2. Tsai M, Chang Y, Schwarcz R, Brookes N. Characterization of L-alpha-aminoadipic acid transport in cultured rat astrocytes. Brain Res. 1996;741:166-73 pubmed
    ..7 +/- 0.4 nmol.min-1.mg-1 protein did not differ from the values for Na(+)-independent glutamate uptake, indicating that L-alpha AA and glutamate are equally good substrates for system x-c...
  3. Tang W, Wong K, Lam Y, Cha S, Cheng C, Fong W. The crystal structure of seabream antiquitin reveals the structural basis of its substrate specificity. FEBS Lett. 2008;582:3090-6 pubmed publisher
    ..On the other hand, Arg300 does not have any specific interaction with the alpha-carboxylate group of the substrate, but is important in maintaining the active site conformation...
  4. Young J. A glial toxin reduces effects of gold thioglucose on the hypothalamus and area postrema. Brain Res Bull. 1988;20:97-104 pubmed
    ..The results suggest that GTG lesion formation may result from an effect of GTG on glia...
  5. Gao Y, Ji R. Light touch induces ERK activation in superficial dorsal horn neurons after inflammation: involvement of spinal astrocytes and JNK signaling in touch-evoked central sensitization and mechanical allodynia. J Neurochem. 2010;115:505-14 pubmed publisher
  6. Horie A, Tomita T, Saiki A, Kono H, Taka H, Mineki R, et al. Discovery of proteinaceous N-modification in lysine biosynthesis of Thermus thermophilus. Nat Chem Biol. 2009;5:673-9 pubmed publisher
    ..This study thus reveals the previously unknown function of a small protein in primary metabolism...
  7. Estévez M, Ollilainen V, Heinonen M. Analysis of protein oxidation markers alpha-aminoadipic and gamma-glutamic semialdehydes in food proteins using liquid chromatography (LC)-electrospray ionization (ESI)-multistage tandem mass spectrometry (MS). J Agric Food Chem. 2009;57:3901-10 pubmed publisher
    ..The analysis of GGS and AAS in real food systems would contribute to the understanding of the precise mechanisms involved in food protein oxidation and shed light on the fate of oxidizing amino acids during food processing and storage...
  8. Xu H, Mao L, Ye S, Paisansathan C, Vetri F, Pelligrino D. Astrocytes are a key conduit for upstream signaling of vasodilation during cerebral cortical neuronal activation in vivo. Am J Physiol Heart Circ Physiol. 2008;294:H622-32 pubmed
    ..Results also revealed contributions from connexin 43, implying a role for gap junctions and/or hemichannels in the signaling process and that signaling from the glia limitans to pial arterioles may involve a diffusible mediator...
  9. He M. Pipecolic acid in microbes: biosynthetic routes and enzymes. J Ind Microbiol Biotechnol. 2006;33:401-7 pubmed
    ..This review focuses on various microbial pathways and enzymes for pipecolic acid synthesis, especially those related to the origination of pipecolic acid moieties in secondary metabolites...

More Information

Publications62

  1. Palmer D, Balogh H, Ma G, Zhou X, Marko M, Kaminskyj S, et al. Synthesis and antifungal properties of compounds which target the alpha-aminoadipate pathway. Pharmazie. 2004;59:93-8 pubmed
    ..Three compounds show moderate inhibition of fungal growth, which can be partially restored by the presence of lysine in the growth medium...
  2. Miyazaki J, Kobashi N, Nishiyama M, Yamane H. Functional and evolutionary relationship between arginine biosynthesis and prokaryotic lysine biosynthesis through alpha-aminoadipate. J Bacteriol. 2001;183:5067-73 pubmed
    ..All these results suggest that lysine biosynthesis in T. thermophilus HB27 is functionally and evolutionarily related to arginine biosynthesis...
  3. Requena J, Chao C, Levine R, Stadtman E. Glutamic and aminoadipic semialdehydes are the main carbonyl products of metal-catalyzed oxidation of proteins. Proc Natl Acad Sci U S A. 2001;98:69-74 pubmed
  4. Feller A, Ramos F, Pierard A, Dubois E. In Saccharomyces cerevisae, feedback inhibition of homocitrate synthase isoenzymes by lysine modulates the activation of LYS gene expression by Lys14p. Eur J Biochem. 1999;261:163-70 pubmed
    ..The data are consistent with the conclusion that inhibition by lysine of Lys14p activation results from the control of alphaAASA production through the feedback inhibition of homocitrate synthase activity...
  5. Chand Goyal T, Eckert J, Droby S, Glickmann E, Atkinson K. Transformation of Candida oleophila and survival of a transformant on orange fruit under field conditions. Curr Genet. 1999;35:51-7 pubmed
    ..The identity of the genetically marked transformant was established by PCR-amplification of a portion of the beta-glucuronidase gene...
  6. Johansson E, Steffens J, Lindqvist Y, Schneider G. Crystal structure of saccharopine reductase from Magnaporthe grisea, an enzyme of the alpha-aminoadipate pathway of lysine biosynthesis. Structure. 2000;8:1037-47 pubmed
    ..We set out to determine the structure of this enzyme as a first step in exploring the structural biology of fungal lysine biosynthesis...
  7. Urakawa K, Mihara M, Suzuki T, Kawamura A, Akamatsu K, Takeda Y, et al. Polyglutamation of antifolates is not required for induction of extracellular release of adenosine or expression of their anti-inflammatory effects. Immunopharmacology. 2000;48:137-44 pubmed
    ..These results suggest that polyglutamation of antifolate is not required for expression of anti-inflammatory effects...
  8. Isobe K, Fukuda N, Nagasawa S. Analysis of selective production of Nalpha-benzyloxycarbonyl-L-aminoadipate-delta-semialdehyde and Nalpha-benzyloxycarbonyl-L-aminoadipic acid by Rhodococcus sp. AIU Z-35-1. J Biosci Bioeng. 2008;105:152-6 pubmed publisher
    ..The optimum pH of N(alpha)-Z-L-AAA production was affected by the instability of N(alpha)-Z-L-AASA dehydrogenase in the alkaline pH region...
  9. Guldbrandt M, Johansen T, Frydenvang K, Brauner Osborne H, Stensbøl T, Nielsen B, et al. Glutamate receptor ligands: synthesis, stereochemistry, and enantiopharmacology of methylated 2-aminoadipic acid analogs. Chirality. 2002;14:351-63 pubmed
    ..g., IC(50) = 300 microM for (2R,4S)-4-methyl-AA (5d)]. The two unsaturated analogs (S)- (7a) and (R)-(E)-Delta(4)-5-methyl-AA (7b) turned out to be a weak AMPA receptor agonist and a weak mixed NMDA/AMPA receptor antagonist, respectively...
  10. Vessal M, Dugani C, Solomon D, McIntyre Burnham W, Ivy G. Might astrocytes play a role in maintaining the seizure-prone state?. Brain Res. 2005;1044:190-6 pubmed
    ..Together, the data indicate that astrocytes may play a role in maintaining the seizure-prone state...
  11. Ye Z, Bhattacharjee J. Lysine biosynthesis pathway and biochemical blocks of lysine auxotrophs of Schizosaccharomyces pombe. J Bacteriol. 1988;170:5968-70 pubmed
    ..These results demonstrated the basic similarity of the AA pathway in S. pombe and Saccharomyces cerevisiae...
  12. Martin J. New aspects of genes and enzymes for beta-lactam antibiotic biosynthesis. Appl Microbiol Biotechnol. 1998;50:1-15 pubmed
    ..Several new beta-lactam antibiotics have been discovered in gram-positive and gram-negative bacteria that will provide new genes for combinatorial synthesis of new molecules...
  13. Miguel Hidalgo J, Shoyama Y, Wanzo V. Infusion of gliotoxins or a gap junction blocker in the prelimbic cortex increases alcohol preference in Wistar rats. J Psychopharmacol. 2009;23:550-7 pubmed publisher
    ..The present data suggest that impaired integrity of glial cells or the gap junctional communication between them in the rat PFC may contribute to changes in ethanol preference...
  14. Miyazaki T, Miyazaki J, Yamane H, Nishiyama M. alpha-Aminoadipate aminotransferase from an extremely thermophilic bacterium, Thermus thermophilus. Microbiology. 2004;150:2327-34 pubmed
    ..These results suggest multiple roles of LysN in several cellular metabolic pathways including lysine and branched-chain amino acid biosyntheses...
  15. Xu H, Ye S, Baughman V, Feinstein D, Pelligrino D. The role of the glia limitans in ADP-induced pial arteriolar relaxation in intact and ovariectomized female rats. Am J Physiol Heart Circ Physiol. 2005;288:H382-8 pubmed
  16. Wilkes P, Meschia G, Teng C, Zhu Y, Wilkening R, Battaglia F. The effect of an elevated maternal lysine concentration on placental lysine transport in pregnant sheep. Am J Obstet Gynecol. 2003;189:1494-500 pubmed
    ..The purpose of this study was to determine whether umbilical lysine uptake can be increased by infusing a lysine solution that does not contain any other amino acid...
  17. Isobe K, Nagasawa S, Tokuta K, Matuura A, Sakaguchi T, Wakao N. A new microbial method for more efficient production of Nalpha-benzyloxycarbonyl-L-aminoadipate delta-semialdehyde and Nalpha-benzyloxycarbonyl-D-aminoadipate delta-semialdehyde. J Biosci Bioeng. 2005;100:288-91 pubmed
    ..Thus, the microbial method proposed here was superior to the chemical and other biochemical methods in simplicity, reaction rate, and yield...
  18. Akagawa M, Sasaki D, Ishii Y, Kurota Y, Yotsu Yamashita M, Uchida K, et al. New method for the quantitative determination of major protein carbonyls, alpha-aminoadipic and gamma-glutamic semialdehydes: investigation of the formation mechanism and chemical nature in vitro and in vivo. Chem Res Toxicol. 2006;19:1059-65 pubmed
    ..In this paper, we describe this analytical technique for simple and precise measurement of AAS and GGS and discuss their formation mechanism in vivo...
  19. Rucker R, Storms D, Sheets A, Tchaparian E, Fascetti A. Biochemistry: is pyrroloquinoline quinone a vitamin?. Nature. 2005;433:E10-1; discussion E11-2 pubmed
    ..Our results call into question the identification of PQQ as a new vitamin...
  20. Gomez D, Lucas Elio P, Sanchez Amat A, Solano F. A novel type of lysine oxidase: L-lysine-epsilon-oxidase. Biochim Biophys Acta. 2006;1764:1577-85 pubmed
  21. Akagawa M, Sasaki T, Suyama K. Oxidative deamination of lysine residue in plasma protein of diabetic rats. Novel mechanism via the Maillard reaction. Eur J Biochem. 2002;269:5451-8 pubmed
    ..Based on these findings, we propose a novel mechanism for the oxidative modification of proteins in diabetes, namely the oxidative deamination of the lysine residue via the Maillard reaction...
  22. Oitate M, Hirota T, Murai T, Miura S, Ikeda T. Covalent binding of rofecoxib, but not other cyclooxygenase-2 inhibitors, to allysine aldehyde in elastin of human aorta. Drug Metab Dispos. 2007;35:1846-52 pubmed
    ..This might be one of the main causes of cardiovascular events by rofecoxib in clinical situations...
  23. Shen W, Li S, Chung S, Gillies M. Retinal vascular changes after glial disruption in rats. J Neurosci Res. 2010;88:1485-99 pubmed publisher
    ..Intravitreal injection of GS siRNA induced similar changes in Müller cells and BRB breakdown. Our data are consistent with the hypothesis that glial dysfunction is a primary contributor to the BRB breakdown in retinal vascular diseases...
  24. Akagawa M, Suyama K. Mechanism of formation of elastin crosslinks. Connect Tissue Res. 2000;41:131-41 pubmed
    ..We also describe the mechanism of DES and IDE crosslinking...
  25. Kobashi N, Nishiyama M, Tanokura M. Aspartate kinase-independent lysine synthesis in an extremely thermophilic bacterium, Thermus thermophilus: lysine is synthesized via alpha-aminoadipic acid not via diaminopimelic acid. J Bacteriol. 1999;181:1713-8 pubmed
    ..All of these results indicated that in T. thermophilus, lysine was not synthesized via the diaminopimelic acid pathway, believed to be common to all bacteria, but via a pathway using alpha-aminoadipic acid as a biosynthetic intermediate...
  26. Nishida H, Nishiyama M. What is characteristic of fungal lysine synthesis through the alpha-aminoadipate pathway?. J Mol Evol. 2000;51:299-302 pubmed
    ..We point out that alpha-aminoadipate reductase is a key enzyme to the evolution of fungal lysine synthesis. In addition, fungi have two different saccharopine dehydrogenases, which is also characteristic of fungi...
  27. Tomita T, Miyagawa T, Miyazaki T, Fushinobu S, Kuzuyama T, Nishiyama M. Mechanism for multiple-substrates recognition of alpha-aminoadipate aminotransferase from Thermus thermophilus. Proteins. 2009;75:348-59 pubmed publisher
    ..The crystal structures and site-directed mutagenesis revealed that intersubunit-electrostatic interactions contribute to the elevated thermostability of this enzyme...
  28. Isobe K, Ishikura K, Shimizu S. Identification and characterization of enzyme catalyzing conversion of N(alpha)-benzyloxycarbonyl-L-aminoadipic-delta-semialdehyde to N(alpha)-benzyloxycarbonyl-L-aminoadipic acid in Aspergillus niger AKU 3302. J Biosci Bioeng. 2008;106:409-11 pubmed publisher
    ..0 mM. Thus, N(alpha)-Z-L-lysine was converted to N(alpha)-Z-L-AAA via N(alpha)-Z-L-AASA by a combination of an amine oxidase with broad substrate specificity and an aldehyde oxidase specific to N(alpha)-Z-L-AASA in A. niger AKU 3302...
  29. Baldwin J, Shiau C, Byford M, Schofield C. Substrate specificity of L-delta-(alpha-aminoadipoyl)-L-cysteinyl-D-valine synthetase from Cephalosporium acremonium: demonstration of the structure of several unnatural tripeptide products. Biochem J. 1994;301 ( Pt 2):367-72 pubmed
    ..s. (e.s.m.s.) and 1H n.m.r. These results clearly indicate that, in common with other peptide synthetases, but in contrast with ribosomal peptide synthesis, ACV synthetase has a relatively broad substrate specificity...
  30. Sadilkova K, Gospe S, Hahn S. Simultaneous determination of alpha-aminoadipic semialdehyde, piperideine-6-carboxylate and pipecolic acid by LC-MS/MS for pyridoxine-dependent seizures and folinic acid-responsive seizures. J Neurosci Methods. 2009;184:136-41 pubmed publisher
    ..The stability study showed that alpha-AASA and P6C were unstable even at -20 degrees C. A careful sample handling with immediate freezing and testing is required for reliable result...
  31. Wang W, Wang W, Mei X, Huang J, Wei Y, Wang Y, et al. Crosstalk between spinal astrocytes and neurons in nerve injury-induced neuropathic pain. PLoS ONE. 2009;4:e6973 pubmed publisher
  32. Feng Q, Wang W, Feng X, Mei X, Zhu C, Liu Z, et al. Astrocytic activation in thoracic spinal cord contributes to persistent pain in rat model of chronic pancreatitis. Neuroscience. 2010;167:501-9 pubmed publisher
    ..Our results provide for the first time that astrocytes may play a critical role in pain of CP. Some actions could be taken to prevent astrocytic activation to treat pain in CP patients...
  33. Barger S, Basile A. Activation of microglia by secreted amyloid precursor protein evokes release of glutamate by cystine exchange and attenuates synaptic function. J Neurochem. 2001;76:846-54 pubmed
  34. Chase L, Peterson N, Koerner J. The lathyrus toxin, beta-N-oxalyl-L-alpha,beta-diaminopropionic acid (ODAP), and homocysteic acid sensitize CA1 pyramidal neurons to cystine and L-2-amino-6-phosphonohexanoic acid. Toxicol Appl Pharmacol. 2007;219:1-9 pubmed
    ..Thus, the results of this study support our previous model of QUIS sensitization and have important implications for the mechanisms of neurotoxicity, neurolathyrism and hyperhomocystinemia...
  35. Montesinos M, Desai A, Delano D, Chen J, Fink J, Jacobson M, et al. Adenosine A2A or A3 receptors are required for inhibition of inflammation by methotrexate and its analog MX-68. Arthritis Rheum. 2003;48:240-7 pubmed
  36. Akagawa M, Sasaki D, Kurota Y, Suyama K. Formation of alpha-aminoadipic and gamma-glutamic semialdehydes in proteins by the maillard reaction. Ann N Y Acad Sci. 2005;1043:129-34 pubmed
    ..0 mM methylglyoxal in the absence and presence of 100 microM Fe3+ for 2 weeks. These results suggest that the Maillard reaction can contribute to the formation of AAS and GGS in vivo...
  37. van der Slot Verhoeven A, van Dura E, Attema J, Blauw B, Degroot J, Huizinga T, et al. The type of collagen cross-link determines the reversibility of experimental skin fibrosis. Biochim Biophys Acta. 2005;1740:60-7 pubmed
    ..In conclusion, our data indicate that the type of collagen cross-linking is an important factor in determining whether the outcome of the fibrotic process is reversible or not...
  38. Akoev G, Andrianov G, Bromm B, Szabo T. Effects of excitatory amino acid antagonists on synaptic transmission in the ampullae of Lorenzini of the skate Raja clavata. J Comp Physiol A. 1991;168:647-52 pubmed
    ..L-ASP was more resistant to blockade by KEN than L-GLU. 8. These observations suggest a prominent physiological role of quisqualate-, kainate- and NMDA-preferring receptors in the ampullae of Lorenzini of Raja clavata...
  39. Billet F, Costentin J, Dourmap N. Influence of glial cells in the dopamine releasing effect resulting from the stimulation of striatal delta-opioid receptors. Neuroscience. 2007;150:131-43 pubmed
  40. Nishida H, Nishiyama M, Kobashi N, Kosuge T, Hoshino T, Yamane H. A prokaryotic gene cluster involved in synthesis of lysine through the amino adipate pathway: a key to the evolution of amino acid biosynthesis. Genome Res. 1999;9:1175-83 pubmed
    ..This lysine biosynthesis cluster is assumed to be one of the origins of lysine biosynthesis and could therefore become a key to the evolution of amino acid biosynthesis...
  41. Park J, Jo J, Zheng H, Patel K, Stern J. Regulation of tonic GABA inhibitory function, presympathetic neuronal activity and sympathetic outflow from the paraventricular nucleus by astroglial GABA transporters. J Physiol. 2009;587:4645-60 pubmed publisher
    ..Altogether, our results indicate that by modulating ambient GABA levels and the efficacy of GABA(A)I(tonic), PVN GATs, of a likely glial location, contribute to setting a basal tone of PVN-RVLM firing activity, and PVN-driven RSNA...
  42. Urakawa K, Mihara M, Takagi N, Kawamura A, Akamatsu K, Takeda Y. Polyglutamation of a novel antifolate, MX-68, is not necessary for its anti-arthritic effect. Eur J Pharmacol. 2002;435:237-44 pubmed
    ..These results indicate that polyglutamation is not essential for the anti-arthritic effect of antifolates...
  43. Trip H, Evers M, Kiel J, Driessen A. Uptake of the beta-lactam precursor alpha-aminoadipic acid in Penicillium chrysogenum is mediated by the acidic and the general amino acid permease. Appl Environ Microbiol. 2004;70:4775-83 pubmed
    ..chrysogenum. The transport measurements demonstrate that both PcGap1 and PcDip5 contribute to the alpha-aminoadipic acid flux...
  44. Kim D, Kim J, Kwak S, Choi K, Kim D, Kwon O, et al. Spatiotemporal characteristics of astroglial death in the rat hippocampo-entorhinal complex following pilocarpine-induced status epilepticus. J Comp Neurol. 2008;511:581-98 pubmed publisher
    ..These findings suggest that regional specific astroglial death/regeneration patterns may play an important role in the pathogenesis of temporal lobe epilepsy...
  45. Watanabe M, Kato Y, Togami K, Yamanaka M, Wakabayashi K, Ogawa H, et al. [Evaluation of gene index for identification of Byssochlamys spp]. Shokuhin Eiseigaku Zasshi. 2008;49:82-7 pubmed
    ..Re-classification will be necessary, based on detailed morphological observations...
  46. Cho K, Chen D. Promoting optic nerve regeneration in adult mice with pharmaceutical approach. Neurochem Res. 2008;33:2126-33 pubmed publisher
    ..They suggest a potential therapeutic strategy for treating optic nerve and CNS damage...
  47. Takeda M, Takamiya A, Jiao J, Cho K, Trevino S, Matsuda T, et al. alpha-Aminoadipate induces progenitor cell properties of Müller glia in adult mice. Invest Ophthalmol Vis Sci. 2008;49:1142-50 pubmed publisher
    ..This study was conducted to determine the signals that can activate this dormant capacity of Müller glia in adult mice, by studying their behavior during glutamate stimulation...
  48. Chen S, Wang J, Garey L, Jen L. Expression of beta-amyloid precursor and Bcl-2 proto-oncogene proteins in rat retinas after intravitreal injection of aminoadipic acid. Neurochem Int. 1999;35:371-82 pubmed
  49. Revelles O, Espinosa Urgel M, Fuhrer T, Sauer U, Ramos J. Multiple and interconnected pathways for L-lysine catabolism in Pseudomonas putida KT2440. J Bacteriol. 2005;187:7500-10 pubmed
    ..This study establishes an unequivocal relationship between gene and pathway enzymes in the metabolism of L-lysine, which is of crucial importance for the successful colonization of the rhizosphere of plants by this microorganism...
  50. Sastry T, Chandrsekaran A, Sundaraseelan J, Ramasastry M, Sreedhar R. Comparative study of some physico-chemical characteristics of osteoporotic and normal human femur heads. Clin Biochem. 2007;40:907-12 pubmed
    ..To compare some of the physico-chemical properties of osteoporotic and normal femur heads -- a sample study...
  51. Rozan P, Kuo Y, Lambein F. Nonprotein amino acids in edible lentil and garden pea seedlings. Amino Acids. 2001;20:319-24 pubmed
    ..Garden pea seedlings also contained a uracil-alanine derivative (isowillardiine) in substantial amount. Some of these compounds such as BIA and alpha-aminoadipic acid have neurotoxic activity...
  52. Kandil S, Brennan L, McBean G. Glutathione depletion causes a JNK and p38MAPK-mediated increase in expression of cystathionine-gamma-lyase and upregulation of the transsulfuration pathway in C6 glioma cells. Neurochem Int. 2010;56:611-9 pubmed publisher
  53. Yamamoto T, Eguchi T. Thiahomoisocitrate: a highly potent inhibitor of homoisocitrate dehydrogenase involved in the alpha-aminoadipate pathway. Bioorg Med Chem. 2008;16:3372-6 pubmed
    ..Kinetic studies suggested that the formation of the enolate intermediate played an important role in inhibition...