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Chemical Compound Review

dehydroalanine     2-aminoprop-2-enoic acid

Synonyms: AG-E-42448, CHEBI:17123, HMDB03609, AC1L3XOY, CTK4E1639, ...
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Disease relevance of DHA


High impact information on DHA


Chemical compound and disease context of DHA

  • In the absence of other substrates, L-Ser reacts rapidly with the tryptophan synthase alpha 2 beta 2 bienzyme from Salmonella typhimurium at pH 7.8 and 25 degrees C to give an equilibrating mixture of species dominated by comparable amounts of the L-Ser external aldimine Schiff base, E(Aex1), and the alpha-aminoacrylate Schiff base, E(A-A) [11].
  • Ancovenin, an inhibitor of angiotensin I converting enzyme isolated from the culture broth of a Streptomyces species, is a dialysable peptide composed of sixteen amino acid residues containing unusual amino acids such as threo-beta-methyllanthionine, meso-lanthionine, and dehydroalanine [12].

Biological context of DHA


Anatomical context of DHA

  • We developed a new assay method for dehydroalanine residues in thyroglobulin, which had been proposed to be the 'lost side chains' during thyroid hormonogenesis [18].
  • The target compounds were designed as mimetics of the dehydroalanine side chain of the macrocyclic antibiotic thiostrepton that acts on the bacterial ribosome [19].
  • One of those compounds, the AD-5 (N-(paramethoxyphenylacetyl) dehydroalanine) has been examined for its ability to decrease the amount of reactive oxygen species which appeared when liver microsomes (isolated from rats pretreated with phenobarbital) are incubated in the presence of Nitrofurantoin (NF) [20].

Associations of DHA with other chemical compounds


Gene context of DHA

  • Moreover, at minimum levels of iodination, when thyroglobulin contains the lowest number of hormone molecules, dehydroalanine is mostly found in the 15,900-Da peptide [10].
  • The reaction occurs via a ping-pong kinetic mechanism in which alpha-aminoacrylate in Schiff base with the active site PLP is an intermediate [Cook, P. F., Hara, S., Nalabolu, S. R., and Schnackerz, K. D. (1992) Biochemistry 31, 2298-2303] [26].
  • Furthermore, the alpha-aminoacrylate Schiff base intermediate, E(A-A), formed between L-Ser and enzyme-bound PLP has an unusual spectrum with lambda(max) = 350 nm and a shoulder extending to greater than 500 nm [27].
  • A chemoselective strategy for oligosaccharide-peptide ligation is described in which alpha-thio analogues of mucin-related glycoconjugates can be readily accessed through site-selective conjugate addition of complex oligosaccharide thiolates to dehydroalanine-containing peptides [28].
  • Use of a dehydroalanine-containing peptide as an efficient inhibitor of tripeptidyl peptidase II [29].

Analytical, diagnostic and therapeutic context of DHA


  1. Broad spectrum thiopeptide recognition specificity of the Streptomyces lividans TipAL protein and its role in regulating gene expression. Chiu, M.L., Folcher, M., Katoh, T., Puglia, A.M., Vohradsky, J., Yun, B.S., Seto, H., Thompson, C.J. J. Biol. Chem. (1999) [Pubmed]
  2. Substitution of pyridoxal 5'-phosphate in the O-acetylserine sulfhydrylase from Salmonella typhimurium by cofactor analogs provides a test of the mechanism proposed for formation of the alpha-aminoacrylate intermediate. Cook, P.F., Tai, C.H., Hwang, C.C., Woehl, E.U., Dunn, M.F., Schnackerz, K.D. J. Biol. Chem. (1996) [Pubmed]
  3. Presence and quantity of dehydroalanine in histidine ammonia-lyase from Pseudomonas putida. Consevage, M.W., Phillips, A.T. Biochemistry (1985) [Pubmed]
  4. Stereoelectronic control of bond formation in Escherichia coli tryptophan synthase: substrate specificity and enzymatic synthesis of the novel amino acid dihydroisotryptophan. Roy, M., Keblawi, S., Dunn, M.F. Biochemistry (1988) [Pubmed]
  5. Some chemical and physical properties of nisin, a small-protein antibiotic produced by Lactococcus lactis. Liu, W., Hansen, J.N. Appl. Environ. Microbiol. (1990) [Pubmed]
  6. Characterization of covalent multimers of crystallins in aging human lenses. Srivastava, O.P., Kirk, M.C., Srivastava, K. J. Biol. Chem. (2004) [Pubmed]
  7. Functional properties of the active core of human cystathionine beta-synthase crystals. Bruno, S., Schiaretti, F., Burkhard, P., Kraus, J.P., Janosik, M., Mozzarelli, A. J. Biol. Chem. (2001) [Pubmed]
  8. Site-directed mutagenesis of conserved serines in rat histidase. Identification of serine 254 as an essential active site residue. Taylor, R.G., McInnes, R.R. J. Biol. Chem. (1994) [Pubmed]
  9. Engineering dehydrated amino acid residues in the antimicrobial peptide nisin. Kuipers, O.P., Rollema, H.S., Yap, W.M., Boot, H.J., Siezen, R.J., de Vos, W.M. J. Biol. Chem. (1992) [Pubmed]
  10. Thyroid hormonogenesis. Identification of a sequence containing iodophenyl donor site(s) in calf thyroglobulin. Palumbo, G. J. Biol. Chem. (1987) [Pubmed]
  11. Evidence of a low-barrier hydrogen bond in the tryptophan synthase catalytic mechanism. Hur, O., Leja, C., Dunn, M.F. Biochemistry (1996) [Pubmed]
  12. Isolation and characterization of ancovenin, a new inhibitor of angiotensin I converting enzyme, produced by actinomycetes. Kido, Y., Hamakado, T., Yoshida, T., Anno, M., Motoki, Y., Wakamiya, T., Shiba, T. J. Antibiot. (1983) [Pubmed]
  13. Cloning and expression of rat histidase. Homology to two bacterial histidases and four phenylalanine ammonia-lyases. Taylor, R.G., Lambert, M.A., Sexsmith, E., Sadler, S.J., Ray, P.N., Mahuran, D.J., McInnes, R.R. J. Biol. Chem. (1990) [Pubmed]
  14. Identification of serine-143 as the most likely precursor of dehydroalanine in the active site of histidine ammonia-lyase. A study of the overexpressed enzyme by site-directed mutagenesis. Langer, M., Reck, G., Reed, J., Rétey, J. Biochemistry (1994) [Pubmed]
  15. Aminoacrylate intermediates in the reaction of Citrobacter freundii tyrosine phenol-lyase. Phillips, R.S., Chen, H.Y., Faleev, N.G. Biochemistry (2006) [Pubmed]
  16. Allosteric regulation of tryptophan synthase: effects of pH, temperature, and alpha-subunit ligands on the equilibrium distribution of pyridoxal 5'-phosphate-L-serine intermediates. Peracchi, A., Bettati, S., Mozzarelli, A., Rossi, G.L., Miles, E.W., Dunn, M.F. Biochemistry (1996) [Pubmed]
  17. Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A. Snider, B.B., Zeng, H. J. Org. Chem. (2003) [Pubmed]
  18. Colorimetry of dehydroalanine residues preserved as 'lost side chains' in thyroglobulin. Kondo, T., Kondo, Y., Ui, N. Mol. Cell. Endocrinol. (1988) [Pubmed]
  19. Synthesis of dehydroalanine fragments as thiostrepton side chain mimetics. Ayida, B.K., Simonsen, K.B., Vourloumis, D., Hermann, T. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  20. AD 5, a dehydroalanine derivative, decreases the amount of reactive oxygen species formed during nitrofurantion microsomal metabolism. Buc-Calderon, P., Roberfroid, M. Life Sci. (1990) [Pubmed]
  21. Formation of dehydroalanine residues during thyroid hormone synthesis in thyroglobulin. Gavaret, J.M., Nunez, J., Cahnmann, H.J. J. Biol. Chem. (1980) [Pubmed]
  22. Letter: alpha-aminoacrylate schiff base in nonenzymatic pyridoxal catalysis. Karube, Y., Matsushima, Y. J. Am. Chem. Soc. (1976) [Pubmed]
  23. Preparation and characterization of anhydrothrombin. Ashton, R.W., Scheraga, H.A. Biochemistry (1995) [Pubmed]
  24. Characterization of the S272A,D site-directed mutations of O-acetylserine sulfhydrylase: involvement of the pyridine ring in the alpha,beta-elimination reaction. Daum, S., Tai, C.H., Cook, P.F. Biochemistry (2003) [Pubmed]
  25. Kinetic isotope effects as a probe of the beta-elimination reaction catalyzed by O-acetylserine sulfhydrylase. Hwang, C.C., Woehl, E.U., Minter, D.E., Dunn, M.F., Cook, P.F. Biochemistry (1996) [Pubmed]
  26. Cysteine 42 is important for maintaining an integral active site for O-acetylserine sulfhydrylase resulting in the stabilization of the alpha-aminoacrylate intermediate. Tai, C.H., Yoon, M.Y., Kim, S.K., Rege, V.D., Nalabolu, S.R., Kredich, N.M., Schnackerz, K.D., Cook, P.F. Biochemistry (1998) [Pubmed]
  27. Proton transfers in the beta-reaction catalyzed by tryptophan synthase. Hur, O., Niks, D., Casino, P., Dunn, M.F. Biochemistry (2002) [Pubmed]
  28. Oligosaccharide-peptide ligation of glycosyl thiolates with dehydropeptides: synthesis of S-linked mucin-related glycopeptide conjugates. Galonić, D.P., Van Der Donk, W.A., Gin, D.Y. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  29. Use of a dehydroalanine-containing peptide as an efficient inhibitor of tripeptidyl peptidase II. Tomkinson, B., Grehn, L., Fransson, B., Zetterqvist, O. Arch. Biochem. Biophys. (1994) [Pubmed]
  30. Identification and characterization of the structural and transporter genes for, and the chemical and biological properties of, sublancin 168, a novel lantibiotic produced by Bacillus subtilis 168. Paik, S.H., Chakicherla, A., Hansen, J.N. J. Biol. Chem. (1998) [Pubmed]
  31. 7-Desmethyl-microcystin-RR, a hepatotoxin from a waterbloom of Microcystis aeruginosa. Martin, C., Weckesser, J., Ino, T., König, W.A., Skulberg, O.M. Z. Naturforsch., C, J. Biosci. (1992) [Pubmed]
  32. Friedel-Crafts-type mechanism for the enzymatic elimination of ammonia from histidine and phenylalanine. Poppe, L., Rétey, J. Angew. Chem. Int. Ed. Engl. (2005) [Pubmed]
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