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Kwas muraminowy znany i nieznany

Autorzy
Identyfikatory
Warianty tytułu
EN
The muramic acid in known and unknown
Języki publikacji
PL
Abstrakty
PL
W pracy opisano stan wiedzy na temat specyficznej cząsteczki zwanej kwasem muraminowym, która występuje w polisacharydach ścian komórkowych bakterii i zarodników. W pracy omówiono jego strukturę, występowanie, właściwości fizykochemiczne, funkcje i przemiany, rolę biologiczna i fizjologiczną oraz metody analizy.
EN
The review describes present knowledge about the very specific molecule namely muramic acid which is an important constituent of bacteria cell walls. Details about physical and chemical characterization are presented with its physiological and biological roles, synthesis, bioconversion. Methods of analytical determination are also described.
Rocznik
Tom
Strony
105--118
Opis fizyczny
Bibliogr. 54 poz.
Twórcy
  • Instytut Podstaw Chemii Żywności, Wydział Biotechnologii i Nauk o Żywności, Politechnika Łódzka
Bibliografia
  • [1] Park J.T.: Uridine-5'-pyrophosphate derivatives. II. A structure common to three derivatives. J. Biol. Chem., 194, 885-895, (1952).
  • [2] Strange R.E., Powell J.F.: Hexosamine-containing peptides in spores of Bacillus subtilis, B. megatherium and B. cereus. Biochem. J., 58, 80-85, (1954).
  • [3] Cummins C.S., Harris H.: Carbohydrate and amino acid constituents of the cell walls of Corynebacterium diphtheriae. Biochem. J., 57, XXXII, (1954).
  • [4] Cummins C.S., Harris H.: The chemical composition of the cell wall in some gram-positive bacteria and its possible value as a taxonomic character. J. Gen. Mikrobiol., 14, 583-600, (1956).
  • [5] Weidel von W., Primosigh J.: The common method of lysis of Escherichia coli by penicillin and phage. Z. Naturf., 12B, 421-427, (1957).
  • [6] Park J.T., Strominger J.L.: Mode of action of penicillin. Science, 125, 99-101, (1957).
  • [7] Kunicki-Goldfinger W.J.H.: Życie bakterii, PWN, Warszawa (2005).
  • [8] Schlegel H.G.: Mikrobiologia ogólna, PWN, Warszawa (2000).
  • [9] Markiewicz Z.: Struktura i funkcje osłon bakteryjnych, PWN, Warszawa (1993).
  • [10] Strange R.E., Dark F.A.: Unidentified amino sugar present in cell walls and spores of various bacteria. Nature, 177, 186-188, (1956).
  • [11] Strange R.E.: The structure of an amino sugar present in certain spores and bacterial cell walls. Biochem. J., 64, 23P, (1956).
  • [12] Kent L.H.: The structure of muramic acid, Biochem. J., 67, 5P, (1957).
  • [13] Strange R.E., Kent L.H., Isolation, characterization, and chemical synthesis of muramic acid. Biochem. J., 71, 333-339, (1959).
  • [14] Lambert F., Zilliken F.: 2-Amino-3-O-(l-carboxyethyl)-2-deoxy-D-glucose and 2-amino-2-deoxy-3-O-ethyl-D-glucose. Ber., 93, 2915-2923, (1960).
  • [15] Matsushima Y., Park J.T.: Stereospecific synthesis of 2-amino-3-O-(D-1-carboxyethyl)-2-deoxy-D-glucose (muramic acid) and related compounds. J. Org. Chem., 27, 3581-3583, (1965).
  • [16] Gigg R., Carroll P.M.: A convenient synthesis of muramic acid and other 3-ethers of 2-amino-2-deoxy-D-glucose. Nature, 191, 495-496, (1961).
  • [17] Lindberg B., Agback H., 3-O-Substituted 2-amino-2-deoxy-D-glucose; oxazoline and N-benzoyl derivatives. Acta Chem. Scand., 18, 185-190, (1964).
  • [18] Flowers H.M., Jeanloz R.W.: Amino sugars. XXXVII. The synthesis of 2-acetamido-3-O-(D-1-carboxyethyl)- 2-deoxy-a -D-glucose (N-acetylmuramic acid) and of banzyl glycoside derivatives of 2-amino-3-O-(D-1-carboxyethyl)-2-deoxy-D-glucose (muramic acid). J. Org. Chem., 28, 2983-2986, (1963).
  • [19] Osawa T., Jeanloz R.W.: Amino sugars. XLII. An improved, stereoselective synthesis of 2-amino-3-O-(D-1-carboxyethyl)-2-deoxy-D-glucose (muramic acid). J. Org. Chem., 30, 448-450, (1965).
  • [20] Cornforth J.W., Firth M.E.: Identification of two chromogens in the Elson-Morgan determination of hexosamines. A new synthesis of 3-methylpyrrole. Structure of the "pyrrolenephthalides". J. Chem. Soc., 1091-1099, (1958).
  • [21] Militzer W.E.: The Kiliani reaction as a direct measure of reducing groups. Arch. Biochem., 9, 91-94, (1946).
  • [22] Ayouba A., Chatelain C., Rouge P.: Legume lectins interact with muramic acid and N-acetylmuramic acid. FEBS-Lett, 289, 102-104, (1991).
  • [23] Pinegin B.V., Kulakov A.V., Yarilin D.A., Klimova S.V., Khaitov R.M.: Competitive analysis of specificity of natural antibodies against the epitope of bacterial cell wall peptidoglycan: glucosaminylmuramyl dipeptide carrying adjuvant activity. Immunol. Infect. Dis., 6, 133-137, (1996).
  • [24] Galdiero M., Cipollaro de l'Ero G., Donnarumma G., Marcatili A., Molitierno M., Petrillo G.: Production of tumor necrosis factor-a , interleukin-1, interleukin-6 and soluble intercellular adhesion molecule-1 by human keratinocytes stimulated in vitro with gram-negative and gram-positive components, i wsp., Immunol. Infect. Dis., 6, 71-80, (1996).
  • [25] Hadzija O.: Simple method for the quantitative determination of muramic acid. Anal. Biochem., 60, 512-517, (1974).
  • [26] Asabe Y., Kojima S., Suzuki M., Takitani S.: Fluorometric determination of acetaldehyde and its related compounds with o-phenylphenol. Anal. Biochem.79, 73-82, (1977).
  • [27] Ghuysen J.M., Ericas E., Leyh-Bouille M., Lache M., Shockman G.D.: Peptide Na-(L-alanyl-D-isoglutaminyl)-Ne-(D-isoasparaginyl)-L-lysyl-D-alanine and the disaccharide N-acetylglucosaminyl-b-1,4,-N-acetylmuramic acid in cell wall peptidoglycan of Streptococcus faecalis strain ATCC 9790., Biochemistry, 6, 2607-2619, (1967).
  • [28] Perkins H.R.: The use of photolysis of dinitrophenyl-peptides in structural studies on the cell-wall mucopeptide of Corynebacterium poinsettiae. Biochem. J., 102, 29c-32c, (1967).
  • [29] Tipper D.J.: Alkali-catalyzed elimination of D-lactic acid from muramic acid and its derivatives and the determination of muramic acid. Biochemistry, 7, 1441-1449, (1968).
  • [30] Roseman S., Dafner L: Colorimetric method for determination of glucosamine and galactosamine. Anal. Chem., 28, 1743-1746, (1956).
  • [31] Cessi C., Piliego F.: Determination of amino sugars in the presence of amino acids and glucose. Biochem. J., 77, 508-510, (1960).
  • [32] Steward-Tull D.E.S.: Determination of amino sugars in mixtures containing glucosamine, galactosamine, and muramic acid. Biochem. J., 109, 13-18, (1968).
  • [33] Valinger Z., Ladesic B., Tomasic J.: Partial purification and characterization of N-acetylmuramyl-L-alanine amidase from human and mouse serum. Biochim. Biophys. Acta, 701, 63-71, (1982).
  • [34] Sesartic L., Hadzija O.: Spectrophotometric determination of N-acetylmuramic acic in complex molecules. Anal. Chim. Acta, 242, 221-224, (1991).
  • [35] Jeanloz R.W., Forchelli E.: Hyaluronic acid and related substances. II. Periodate oxidation of glucosamine and derivatives. J. Biol. Chem., 188, 361-369, (1951).
  • [36] O'Dea I.F., Gibbons R.A.: Estimation of small amounts of formaldehyde liberated during the oxidation of carbohydrates and other substances with periodate. Biochem. J., 55, 580-586, (1953).
  • [37] Brownlee S.T., Ph.D.Dissertation, Duke Univ. (1963).
  • [38] Spackman D.H., Stein W.H., Moore S.: Automatic recording apparatus for use in the chromatography of amino acids. Anal. Chem., 30, 1190-1205, (1958).
  • [39] Zeleznick L.D.: Sephadex G-25 in partition column chromatography. J. Chromatogr., 14, 139-141, (1964).
  • [40] Esser K.: Determination of microamounts of amino acids and amino sugars by thin-layer chromatography. J. Chromatogr., 18, 414-416, (1965).
  • [41] Fox A., Morgan S.L., Hudson J.R., Zhu Z.T., Lau P.Y.: Capillary gas chromatographic analysis of alditol acetates of neutral and amino sugars in bacterial cell walls. J. Chromatogr., 256, 429-438, (1983).
  • [42] Tomasic J., Sesartic L., Martin S.A., Valinger Z., Ladesic B.: Comparative susceptibility of a peptidoglycan monomer from Brevibacterium divaricatum and its anhydromuramyl analog to hydrolysis with N-acetylmuramyl-L-alanine amidase. Isolation and characterization of anhydromuramyl-peptidoglycan monomer. J. Chromatogr., 440, 405-414, (198).
  • [43] Mielniczuk Z., Mielniczuk E., Larsson L.: Determination of muramic acid in organic dust by gas chromatography-mass spectrometry. J. Chromatogr. B: Biomed. Appl., 670, 167-172, (1995).
  • [44] Fox A., Rosario R.M.T., Larsson L.: Monitoring of bacterial sugars and hydroxyl fatty acids in dust from air conditioners by gas chromatography-mass spectrometry. Appl. Environ. Microbiol., 59, 4354-4360, (1993).
  • [45] Fox A., Wright L., Fox K.: Gas chromatography-tandem mass spectrometry for trace detection of muramic acid, a peptidoglycan chemical marker, in organic dust. J. Microbiol. Methods, 22, 11-26, (1995).
  • [46] Lehtonen L., Eerola E., Toivanen P.: Muramic acid in human peripheral blood leukocytes in different age groups. Eur. J. Clin. Invest., 27, 791-792, (1997).
  • [47] Fox K., Wunschel D.S., Fox A., Steward G.: Complementarity of GC-MS and LC-MS analyses for determination of carbohydrate profiles of vegetative cells and spores of bacilli. J. Microbiol. Methods, 33, 1-11, (1998).
  • [48] Fox A., Krahmer M., Harrelson D.: Monitoring muramic acid in air (after alditol acetate derivatization) using a gas chromatograph-ion trap tandem mass spectrometer. J. Microbiol. Methods, 27, 129-138, (1996).
  • [49] Black G.E., Fox A., Fox K., Snyder A.P., Smith P.B.W.: Electrospray Tandem Mass Spectrometry for Analysis of Native Muramic Acid in Whole Bacterial Cell Hydrolyzates. Anal. Chem., 66, 4171-4176, (1994).
  • [50] Bal K., Larsson L.: New and simple procedure for the determination of muramic acid in chemically complex environments by gas chromatography-ion trap tandem mass spectrometry. J. Chromatogr. B, 738, 57-65, (2000).
  • [51] Kozar M.P., Fox A.: Analysis of a stable halogenated derivative of muramic acid by gas chromatography-negative ion chemical ionization tandem mass spectrometry. J. Chromatogr. A, 946, 229-238, (2002).
  • [52] Bal K., Larsson L., Mielniczuk E., Mielniczuk Z.: Structure of muramic acid TMS derivative mass spectrum's base ion (m/z = 185) used for quantification of bacterial peptidoglycan. J. Microbiol. Methods, 48, 267-270, (2002).
  • [53] Lee J., Hollingsworth R.I.: Oligosaccharide beta-glucans with unusual linkages from Sarcina ventriculi. Carbohydrate Research, 304, 133-141, (1997).
  • [54] Keglevic D., Ladesic B., Tomasic J., Valinger Z., Naumski R.: Isolation procedure and properties of monomer unit from lysozyme digest of peptidoglycan complex excreted into the medium by penicillin-treated Brevibacterium divaricatum mutant. Biochim. Biophys. Acta, 585, 273-281, (1979).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-LOD7-0012-0009
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