aminoisobutyric acids

Summary

Summary: A group of compounds that are derivatives of the amino acid 2-amino-2-methylpropanoic acid.

Top Publications

  1. Gessmann R, Brückner H, Petratos K. Three complete turns of a 3(10)-helix at atomic resolution: the crystal structure of Z-(Aib)11-OtBu. J Pept Sci. 2003;9:753-62 pubmed
    ..Helical columns are packed via apolar crystal contacts. The crystal structure of Z-(Aib)11-OtBu is compared with the crystal structures of Z-(Aib)10-OtBu and Z-(Aib)9-OtBu. The similarities and differences are analysed...
  2. van Kuilenburg A, Stroomer A, van Lenthe H, Abeling N, van Gennip A. New insights in dihydropyrimidine dehydrogenase deficiency: a pivotal role for beta-aminoisobutyric acid?. Biochem J. 2004;379:119-24 pubmed
    ..Furthermore, the observation that the R-enantiomer of beta-AIB is abundantly present in the urine of DPD patients suggests that significant cross-over exists between the thymine and valine catabolic pathways...
  3. Tachikawa E, Nogimori K, Takahashi S, Mizuma K, Itoh K, Kashimoto T, et al. Pathway for Ca2+ influx into cells by trichosporin-B-VIa, an alpha-aminoisobutyric acid-containing peptide, from the fungus Trichoderma polysporum. Biochim Biophys Acta. 1996;1282:140-8 pubmed
    ..On the other hand, the peptide at the higher concentrations seems to damage cell membranes...
  4. Konkoľová J, Chandoga J, Kováčik J, Repiský M, Kramarová V, Paučinová I, et al. Severe child form of primary hyperoxaluria type 2 - a case report revealing consequence of GRHPR deficiency on metabolism. BMC Med Genet. 2017;18:59 pubmed publisher
    ..Several facts support an assumption that catabolic conditions in our patient could worsen the degree of hyperoxaluria and glyceric aciduria as a consequence of the elevated production of free amino acids and their intermediary products. ..
  5. Karl P, Teichberg S, Fisher S. Na(+)-dependent amino acid uptake by human placental microvillous membrane vesicles: importance of storage conditions and preservation of cytoskeletal elements. Placenta. 1991;12:239-50 pubmed
    ..These data, especially with regard to storage conditions, highlight the importance of precise definition of preparation and storage conditions when interpreting results of amino acid uptake by human placental MMV...
  6. Kittel A, Maas R, Konig J, Mieth M, Weiss N, Jarzebska N, et al. In vivo evidence that Agxt2 can regulate plasma levels of dimethylarginines in mice. Biochem Biophys Res Commun. 2013;430:84-9 pubmed publisher
    ..The effect of BAIB excess on endogenous dimethylarginine levels may have direct clinical implications for humans with the relatively common genetic trait of hyper-?-aminoisobutyric aciduria...
  7. Yaplito Lee J, Pitt J, Meijer J, Zoetekouw L, Meinsma R, van Kuilenburg A. Beta-ureidopropionase deficiency presenting with congenital anomalies of the urogenital and colorectal systems. Mol Genet Metab. 2008;93:190-4 pubmed
    ..Long-term follow-up is required to determine the clinical significance of the beta-ureidopropionase deficiency in our patient...
  8. Inai Y, Ousaka N, Okabe T. Mechanism for the noncovalent chiral domino effect: new paradigm for the chiral role of the N-terminal segment in a 3(10)-helix. J Am Chem Soc. 2003;125:8151-62 pubmed
  9. Fabris L, Antonello S, Armelao L, Donkers R, Polo F, Toniolo C, et al. Gold nanoclusters protected by conformationally constrained peptides. J Am Chem Soc. 2006;128:326-36 pubmed
    ..The IR and NMR spectra indicated that in the monolayer the peptides are involved in both intra- and interligand C=O...H-N hydrogen bonds...

More Information

Publications62

  1. Sferruzzi Perri A, Owens J, Standen P, Taylor R, Heinemann G, Robinson J, et al. Early treatment of the pregnant guinea pig with IGFs promotes placental transport and nutrient partitioning near term. Am J Physiol Endocrinol Metab. 2007;292:E668-76 pubmed
    ..This was consistent with the previously observed increase in fetal growth and survival following IGF treatment...
  2. Lang K, Kuki A. Long-range electron transfer in rigid 3(10)-helical oligopeptides containing redox cyclic alpha-amino acids. Photochem Photobiol. 1999;70:579-84 pubmed
    ..These well-defined and sterically stable frameworks are suited for the precise evaluation of intrahelical electron transfer processes mediated by peptides...
  3. Lavoinne A, Meisse D, Quillard M, Husson A, Renouf S, Yassad A. Glutamine and regulation of gene expression in rat hepatocytes: the role of cell swelling. Biochimie. 1998;80:807-11 pubmed
    ..The effect of glutamine on the regulation of gene expression may be explained, at least in part, by the cell swelling due to its sodium-dependent transport. The physiological significance of the effect of glutamine is discussed...
  4. Iwanishi M, Haruta T, Takata Y, Ishibashi O, Sasaoka T, Egawa K, et al. A mutation (Trp1193-->Leu1193) in the tyrosine kinase domain of the insulin receptor associated with type A syndrome of insulin resistance. Diabetologia. 1993;36:414-22 pubmed
    ..These results suggest that this mutation causes defective tyrosine kinase activity of the insulin receptor, which results in insulin resistance. Insulin action and phenotypic appearance may be mediated by different factors...
  5. Yu J, Zvarec O, Huang D, Bissett M, Scanlon D, Shapter J, et al. Electron transfer through ?-peptides attached to vertically aligned carbon nanotube arrays: a mechanistic transition. Chem Commun (Camb). 2012;48:1132-4 pubmed publisher
    ..Helical structures (Aib units ?3) undergo an electron hopping mechanism, while shorter disordered sequences (Aib units <3) undergo an electron superexchange mechanism...
  6. Vogel K, Arning E, Wasek B, Bottiglieri T, Gibson K. Non-physiological amino acid (NPAA) therapy targeting brain phenylalanine reduction: pilot studies in PAHENU2 mice. J Inherit Metab Dis. 2013;36:513-23 pubmed publisher
  7. Aravinda S, Shamala N, Balaram P. Aib residues in peptaibiotics and synthetic sequences: analysis of nonhelical conformations. Chem Biodivers. 2008;5:1238-62 pubmed publisher
    ..Examples of Aib residues in unusual conformations are illustrated by surveying a database of Aib-containing crystal structures...
  8. Carlotto S, Zerbetto M, Shabestari M, Moretto A, Formaggio F, Crisma M, et al. In silico interpretation of cw-ESR at 9 and 95 GHz of mono- and bis- TOAC-labeled Aib-homopeptides in fluid and frozen acetonitrile. J Phys Chem B. 2011;115:13026-36 pubmed publisher
  9. Black K, Chio C. Increased opening of blood-tumour barrier by leukotriene C4 is dependent on size of molecules. Neurol Res. 1992;14:402-4 pubmed
    ..Increased permeability within tumours after LTC4 infusion is dependent on molecular size. This suggests that LTC4 opens tight junctions rather than increases vesicular transport through endothelial cells...
  10. Fox M, White J, Hosie A, Lodwig E, Poole P. Osmotic upshift transiently inhibits uptake via ABC transporters in gram-negative bacteria. J Bacteriol. 2006;188:5304-7 pubmed
    ..ABC systems were also inactivated in isolated pea bacteroids, probably due to the obligatory use of high-osmolarity isolation media. Measurement of nutrient cycling in isolated pea bacteroids is impeded by this effect...
  11. Olsson S, Sagstuen E, Bonora M, Lund A. EPR dosimetric properties of 2-methylalanine: EPR, ENDOR and FT-EPR investigations. Radiat Res. 2002;157:113-21 pubmed
    ..T(2) was estimated to be of the order of 200-300 ns...
  12. Stevenson D, Milligan S, Collins W. Effects of platelet-derived endothelial cell growth factor/thymidine phosphorylase, substrate, and products in a three-dimensional model of angiogenesis. Am J Pathol. 1998;152:1641-6 pubmed
    ..Drugs that inhibit PD-ECGF/TP activity may therefore delay abnormal angiogenesis and the progression of various cancers...
  13. Gero A, Day R, Hall S. Stimulated transport of adenosine, guanosine and hypoxanthine in Crithidia luciliae: metabolic machinery in which the parasite has a distinct advantage over the host. Int J Parasitol. 1997;27:241-9 pubmed
    ..luciliae to the concentration of purines available at any time to the parasite...
  14. Gerencser G, Loo S. Transport energetics of the Na+ pump in Aplysia californica gut. Can J Physiol Pharmacol. 2001;79:822-4 pubmed
  15. Tanaka M, Oba M, Ichiki T, Suemune H. Solid-state conformation of a hybrid tripeptide between beta-amino acid; 8-aminocyclooct-4-enecarboxylic acid and 2-aminoisobutyric acid. Chem Pharm Bull (Tokyo). 2001;49:1178-81 pubmed
    ..A hybrid tripeptide containing this eight-membered cyclic beta-amino acid and 2-aminoisobutyric acids was synthesized by conventional solution methods...
  16. Jones J, Diemer V, Adam C, Raftery J, Ruscoe R, Sengel J, et al. Length-Dependent Formation of Transmembrane Pores by 310-Helical ?-Aminoisobutyric Acid Foldamers. J Am Chem Soc. 2016;138:688-95 pubmed publisher
    ..Planar bilayer conductance measurements showed that Aib11 and Aib13, but not Aib7, could form pores. This pore-forming behavior is strong evidence that Aibm (m ? 10) building blocks can span bilayers...
  17. Nandel F, Sahrawat T. Conformational study of poly-DeltaAbu peptides and construction of amphipathic nanostructure. Biopolymers. 2009;92:44-51 pubmed publisher
    ..This structure is stabilized by network of hydrogen bonding, carbonyl-carbonyl, and CH-O interactions and can be exploited for the construction of antimicrobial peptides and nanomaterials...
  18. Chi O, Hunter C, Liu X, Tan T, Weiss H. Effects of VEGF on the blood-brain barrier disruption caused by hyperosmolarity. Pharmacology. 2008;82:187-92 pubmed publisher
    ..However, upregulation of VEGF with CPX did not alter the degree of hyperosmolar BBB disruption with or without anti-VEGF antibody treatment. This study suggests that the contribution of VEGF in hyperosmolar BBB disruption is limited...
  19. Chi O, Hunter C, Liu X, Weiss H. The effects of isoflurane pretreatment on cerebral blood flow, capillary permeability, and oxygen consumption in focal cerebral ischemia in rats. Anesth Analg. 2010;110:1412-8 pubmed publisher
    ..Because inducible nitric oxide synthase (iNOS) was implicated as one of the mechanisms of isoflurane preconditioning, the effect of iNOS inhibition on rCBF was also studied...
  20. Ghattas W, Giorgi M, Mekmouche Y, Tanaka T, Rockenbauer A, Reglier M, et al. Identification of a copper(I) intermediate in the conversion of 1-aminocyclopropane carboxylic acid (ACC) into ethylene by Cu(II)-ACC complexes and hydrogen peroxide. Inorg Chem. 2008;47:4627-38 pubmed publisher
    ..We propose Cu(I)-OOH as a possible active species for the conversion of ACC into ethylene, the structure of which was examined by DFT calculation...
  21. Qin L, He J, Lee S, Dodd I. An assessment of the role of ethylene in mediating lettuce (Lactuca sativa) root growth at high temperatures. J Exp Bot. 2007;58:3017-24 pubmed
    ..Although ethylene is important in regulating root morphology and elongation at A-RZT, the failure of ethylene biosynthesis inhibitors to influence shoot carbon gain limits their use in ameliorating the growth inhibition induced by A-RZT...
  22. Zhao M, Bada J. Determination of alpha-dialkylamino acids and their enantiomers in geological samples by high-performance liquid chromatography after derivatization with a chiral adduct of o-phthaldialdehyde. J Chromatogr A. 1995;690:55-63 pubmed
    ..The estimated detection limit for alpha-dialkylamino acids is 1-2 pmol, comparable to that for protein amino acids...
  23. Spitsyna N, Spitsyn V, Deryabin V. Genetic analysis of reproduction in the Buryat populations. J Physiol Anthropol Appl Human Sci. 2005;24:345-9 pubmed
    ..The results obtained widened current knowledge about the influence of genetic and environmental components on reproduction processes in human populations...
  24. Sopasis G, Canaj A, Philippidis A, Siczek M, Lis T, O Brien J, et al. Heptanuclear heterometallic [Cu6Ln] clusters: trapping lanthanides into copper cages with artificial amino acids. Inorg Chem. 2012;51:5911-8 pubmed publisher
    ..Finally, complexes 2, 5-8, 10, and 12 were analyzed using positive ion electrospray mass spectrometry (ES-MS), establishing the structural integrity of the heterometallic heptanuclear cage structure in acetonitrile...
  25. Tsuji A, Kato K, Sugyo A, Okada M, Sudo H, Yoshida C, et al. Comparison of 2-amino-[3-¹¹C]isobutyric acid and 2-deoxy-2-[¹?F]fluoro-D-glucose in nude mice with xenografted tumors and acute inflammation. Nucl Med Commun. 2012;33:1058-64 pubmed publisher
    ..2-Amino-[3-11C]isobutyric acid ([3-11C]AIB) is a potential PET tracer for this purpose. We compared [3-11C]AIB and [18F]FDG uptakes in tumors and acute inflammation in a mouse model...
  26. Quesada A, McGivan J. A rapid method for the functional reconstitution of amino acid transport systems from rat liver plasma membranes. Partial purification of System A. Biochem J. 1988;255:963-9 pubmed
    ..By using this reconstitution procedure, System A transport activity was partially purified by lectin-affinity chromatography...
  27. Hawley D, Maddux B, Patel R, Wong K, Mamula P, Firestone G, et al. Insulin receptor monoclonal antibodies that mimic insulin action without activating tyrosine kinase. J Biol Chem. 1989;264:2438-44 pubmed
    ..These data suggest, therefore, that activation of insulin receptor tyrosine kinase may not be an obligatory step in all of the transmembrane signaling mechanisms of the insulin receptor...
  28. PYSH L, Alexander N, Swatzyna L, Harbert R. Four alleles of AtCESA3 form an allelic series with respect to root phenotype in Arabidopsis thaliana. Physiol Plant. 2012;144:369-81 pubmed
  29. Mackenzie B, Panayotova Heiermann M, Loo D, Lever J, Wright E. SAAT1 is a low affinity Na+/glucose cotransporter and not an amino acid transporter. A reinterpretation. J Biol Chem. 1994;269:22488-91 pubmed
    ..Phlorizin inhibited the alpha MG-evoked current with apparent Ki of 18 microM at -50 mV. We conclude that the SAAT1 cDNA encodes a renal low affinity Na+(1)/glucose(1) cotransporter and propose that pig SAAT1 be renamed pSGLT2...
  30. Kato K, Tsuji A, Saga T, Zhang M. An efficient and expedient method for the synthesis of 11C-labeled ?-aminoisobutyric acid: a tumor imaging agent potentially useful for cancer diagnosis. Bioorg Med Chem Lett. 2011;21:2437-40 pubmed publisher
    ..A comparative tumor positron emission tomography (PET) imaging study using the same model mouse showed higher uptake of 2 than with (11)C-labeled methionine and [(18)F] fluorodeoxyglucose (FDG)...
  31. Prabakaran A, Muthu S. Normal coordinate analysis and vibrational spectroscopy (FT-IR and FT-Raman) studies of (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid using ab initio HF and DFT method. Spectrochim Acta A Mol Biomol Spectrosc. 2012;99:90-6 pubmed publisher
    ..Finally, the calculation results were applied to simulate infrared and Raman spectra of the title compound which shows good agreement with observed spectra...
  32. Caruso M, Placidi E, Gatto E, Mazzuca C, Stella L, Bocchinfuso G, et al. Fibrils or globules? Tuning the morphology of peptide aggregates from helical building blocks. J Phys Chem B. 2013;117:5448-59 pubmed publisher
    ..AFM imaging revealed the formation of globular or fibrillar structures, the predominance of which is controlled by the helix length of the peptide building block...
  33. Nandakumaran M, Harouny A, Al Yatama M, Al Azemi M, Sugathan T. Effect of increased glucose load on maternal-fetal transport of alpha-aminoisobutyric acid in the perfused human placenta: in vitro study. Acta Diabetol. 2002;39:75-81 pubmed
    ..We conclude that hyperglycemia may play a deleterious role in limiting maternal-fetal transport of A-type amino acids in the in vivo state...
  34. Brown Z, Schafmeister C. Exploiting an inherent neighboring group effect of alpha-amino acids to synthesize extremely hindered dipeptides. J Am Chem Soc. 2008;130:14382-3 pubmed publisher
    ..We propose that the reaction proceeds through a previously unexploited intramolecular O,N-acyl transfer pathway...
  35. Jeremic T, Linden A, Heimgartner H. New 21- and 24-atom Aib-containing cyclopeptides. J Pept Sci. 2008;14:1051-61 pubmed publisher
    ..Six intramolecular hydrogen bonds stabilise the structure characterised by two consecutive type II'/I beta-turns, two consecutive type II/III' beta-turns, one gamma-turn, and one inverse gamma-turn...
  36. Chi O, Liu X, Weiss H. Effects of mild hypothermia on blood-brain barrier disruption during isoflurane or pentobarbital anesthesia. Anesthesiology. 2001;95:933-8 pubmed
  37. Schweitzer Stenner R, Gonzales W, Bourne G, Feng J, Marshall G. Conformational manifold of alpha-aminoisobutyric acid (Aib) containing alanine-based tripeptides in aqueous solution explored by vibrational spectroscopy, electronic circular dichroism spectroscopy, and molecular dynamics simulations. J Am Chem Soc. 2007;129:13095-109 pubmed
    ..They also revealed the dynamics and pathways of potential conformational transitions of the corresponding Aib residues...
  38. Formaggio F, Crisma M, Scipionato L, Antonello S, Maran F, Toniolo C. Synthesis and characterization of a series of homooligopeptide peroxyesters. Org Lett. 2004;6:2753-6 pubmed
    ..In each of the six oligomers synthesized, the chain of alpha-amino acids is separated from the peroxyester function by a beta-amino acid. [structure: see text]..
  39. Coulson R, Johnson R, Olsson R, Cooper D, Scheinman S. Adenosine stimulates phosphate and glucose transport in opossum kidney epithelial cells. Am J Physiol. 1991;260:F921-8 pubmed
    ..It is likely that both protein kinases A and C are involved in these actions of adenosine...
  40. Blind P, Waldenstrom A, Hafström L, Berggren D, Ronquist G. Unique antitumour effects of L-2,4 diaminobutyric acid on cultured hepatoma cells. Anticancer Res. 2003;23:1245-8 pubmed
    ..This was combined with a tumour cell energy crisis in attempts to restore the Na(+)-gradient...
  41. Kamenosono T, Shimada H, Funakoshi T, Kojima S. Involvement of active transport systems in the mobilization of cadmium by dithiocarbamates in vivo. Toxicology. 2002;170:103-10 pubmed
  42. Kanamori K, Ross B. Quantitative determination of extracellular glutamine concentration in rat brain, and its elevation in vivo by system A transport inhibitor, alpha-(methylamino)isobutyrate. J Neurochem. 2004;90:203-10 pubmed
  43. Pellegrino R, Martins T, Pinto C, Schein V, Kucharski L, da Silva R. Effect of starvation and refeeding on amino acid metabolism in muscle of crab Neohelice granulata previously fed protein- or carbohydrate-rich diets. Comp Biochem Physiol A Mol Integr Physiol. 2013;164:29-35 pubmed publisher
    ..Protein or carbohydrate levels in the diet administered to this crab modulate the carbon flux between the different metabolic pathways...
  44. Coan P, Vaughan O, McCarthy J, Mactier C, Burton G, Constancia M, et al. Dietary composition programmes placental phenotype in mice. J Physiol. 2011;589:3659-70 pubmed publisher
    ..This has important implications for the intrauterine programming of life expectancy...
  45. Sferruzzi Perri A, Owens J, Standen P, Roberts C. Maternal insulin-like growth factor-II promotes placental functional development via the type 2 IGF receptor in the guinea pig. Placenta. 2008;29:347-55 pubmed publisher
    ..This suggests that maternal IGF-II in early gestation acts in part via the IGF2R to persistently enhance placental functional development and nutrient delivery and promote fetal growth...
  46. Muacevic A, Peller M, Ruprecht L, Berg D, Fend L, Sroka R, et al. Image guided interstitial laser thermotherapy: a canine model evaluated by magnetic resonance imaging and quantitative autoradiography. Acta Neurochir (Wien). 2005;147:175-85; discussion 185-6 pubmed
  47. Rhee Y, Lee W, Lee E, Ma S, Park S, Lim S. In vitro and in vivo effect of parathyroid hormone analogue (1-14) containing -amino-iso-butyric acid residue (Aib)1,3. Yonsei Med J. 2006;47:214-22 pubmed
    ..In conclusion, our findings suggest that unacetylated Aib1,3PTH (1-14) did not exhibit any anabolic effects at the bones of ovariectomized rats...
  48. Harris A, Robinson R, Koehler R, Traystman R, Gleason C. Blood-brain barrier permeability during dopamine-induced hypertension in fetal sheep. J Appl Physiol (1985). 2001;91:123-9 pubmed
    ..We conclude that a 40% increase in mean arterial pressure during dopamine infusion in normoxic fetal sheep does not produce substantial BBB disruption or cerebral edema even as early as 0.6 gestation...
  49. Wada S, Tsuda H, Okada T, Urata H. Cellular uptake of Aib-containing amphipathic helix peptide. Bioorg Med Chem Lett. 2011;21:5688-91 pubmed publisher
    ..In contrast, MAP was poorly taken up by the cell. These results indicate that the incorporation of Aib residues into CPPs markedly improves cellular uptake and MAP(Aib) may be a useful tool for the delivery of hydrophilic macromolecules...
  50. Demizu Y, Nagoya S, Shirakawa M, Kawamura M, Yamagata N, Sato Y, et al. Development of stapled short helical peptides capable of inhibiting vitamin D receptor (VDR)-coactivator interactions. Bioorg Med Chem Lett. 2013;23:4292-6 pubmed publisher
    ..The effects of these peptides on the human VDR were examined in an inhibition assay based on the receptor cofactor assay system, and one of them, DPI-07, exhibited potent inhibitory activity (IC??: 3.2 ?M)...
  51. Gessmann R, Brückner H, Petratos K. The peptide Z-Aib-Aib-Aib-L-Ala-OtBu. Acta Crystallogr C Struct Chem. 2014;70:405-7 pubmed publisher
    ..There are two 4?1 intramolecular hydrogen bonds in the structure. In the lattice, molecules are hydrogen bonded to form columns along the c axis. ..
  52. Takasu A, Houjyou T, Inai Y, Hirabayashi T. Three-dimensional arrangement of sugar residues along a helical polypeptide backbone: synthesis of a new type of periodic glycopeptide by polymerization of a beta-O-glycosylated tripeptide containing alpha-aminoisobutyric acid. Biomacromolecules. 2002;3:775-82 pubmed
    ..Addition of ethanol to aqueous solutions of the periodic glycopolymer 16 resulted in an increase in the alpha-helix content. Semiempirical molecular orbital calculation also supported the alpha-helical conformation of 16...
  53. Zhou L, Antonucci V, Biba M, Gong X, Ge Z. Simultaneous enantioseparation of a basic active pharmaceutical ingredient compound and its neutral intermediate using reversed phase and normal phase liquid chromatography with a new type of polysaccharide stationary phase. J Pharm Biomed Anal. 2010;51:153-7 pubmed publisher
    ..No matrix interference was observed across the elution windows of compound-A and its intermediate. Additionally, the peak purity of each enantiomer was evaluated by mass spectra, indicating the specificity of the method...