231
Views
14
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of L-Rhamnose and N-Acetyl-D-Glucosamine Derivatives Entering in the Composition of Bacterial Polysaccharides by Use of Glucansucrases

, , , , &
Pages 142-160 | Received 13 Nov 2008, Accepted 16 Jan 2009, Published online: 01 Apr 2009

REFERENCES

  • Henrissat , B. 1991 . A classification of glycosyl hydrolases based on amino acid sequence similarities . Biochem. J. , 280 : 309 – 316 . (Pt 2)
  • Robyt , J. F. and Walseth , T. F. 1978 . The mechanism of acceptor reactions of Leuconostoc mesenteroides B-512F dextransucrase . Carbohydr. Res. , 61 : 433 – 445 .
  • Monchois , V. , Willemot , R. M. and Monsan , P. 1999 . Glucansucrases: mechanism of action and structure-function relationships . FEMS Microbiol. Rev. , 23 ( 2 ) : 131 – 151 .
  • Dols , M. , Remaud-Simeon , M. , Willemot , R. M. , Vignon , M. and Monsan , P. 1998 . Characterization of the different dextransucrase activities excreted in glucose, fructose, or sucrose medium by Leuconostoc mesenteroides NRRL B-1299 . Appl. Environ. Microbiol. , 64 ( 4 ) : 1298 – 1302 .
  • Bourne , E. J. , Sidebotham , R. L. and Weigel , H. 1974 . Studies on dextrans and dextranases. XI. The structure of a dextran elaborated by Leuconostoc mesenteroides NRRL B-1299 . Carbohydr. Res. , 34 ( 2 ) : 279 – 288 .
  • Kobayashi , M. , Mitsuishi , Y. , Takagi , S. and Matsuda , K. 1984 . Enzymic degradation of water-soluble dextran from Leuconostoc mesenteroides NRRL B-1299 . Carbohydr. Res. , 127 : 305 – 317 .
  • De Montalk , G. P. , Remaud-Simeon , M. , Willemot , R. M. , Planchot , V. and Monsan , P. 1999 . Sequence analysis of the gene encoding amylosucrase from Neisseria polysaccharea and characterization of the recombinant enzyme . J. Bacteriol. , 181 ( 2 ) : 375 – 381 .
  • van Hijum , S. A. , Kralj , S. , Ozimek , L. K. , Dijkhuizen , L. and van Geel-Schutten , I. G. 2006 . Structure-function relationships of glucansucrase and fructansucrase enzymes from lactic acid bacteria . Microbiol. Mol. Biol. Rev. , 70 ( 1 ) : 157 – 176 .
  • van Leeuwen , S. S. , Kralj , S. , van Geel-Schutten , I. H. , Gerwig , G. J. , Dijkhuizen , L. and Kamerling , J. P. 2008 . Structural analysis of the alpha-D-glucan (EPS35-5) produced by the Lactobacillus reuteri strain 35-5 glucansucrase GTFA enzyme . Carbohydr. Res. , 343 ( 7 ) : 1251 – 1265 .
  • van Leeuwen , S. S. , Kralj , S. , van Geel-Schutten , I. H. , Gerwig , G. J. , Dijkhuizen , L. and Kamerling , J. P. 2008 . Structural analysis of the alpha-D-glucan (EPS180) produced by the Lactobacillus reuteri strain 180 glucansucrase GTF180 enzyme . Carbohydr. Res. , 343 ( 7 ) : 1237 – 1250 .
  • Cote , G. L. , Holt , S. M. and Miller-Fosmore , C. M. 2003 . Prebiotic oligosaccharides via alternansucrase acceptor reactions . ACS Symp. Ser. , 849 : 76 – 89 .
  • Arguello Morales , M. A. , Remaud-Simeon , M. , Willemot , R. M. , Vignon , M. R. and Monsan , P. 2001 . Novel oligosaccharides synthesized from sucrose donor and cellobiose acceptor by alternansucrase . Carbohydr. Res. , 331 ( 4 ) : 403 – 411 .
  • Yoon , S. H. and Robyt , J. F. 2002 . Synthesis of acarbose analogues by transglycosylation reactions of Leuconostoc mesenteroides B-512FMC and B-742CB dextransucrases . Carbohydr. Res. , 337 ( 24 ) : 2427 – 2435 .
  • Cote , G. L. , Dunlap , C. A. , Appell , M. and Momany , F. A. 2005 . Alternansucrase acceptor reactions with D-tagatose and L-glucose . Carbohydr. Res. , 340 ( 2 ) : 257 – 262 .
  • Richard , G. , Yu , S. , Monsan , P. , Remaud-Simeon , M. and Morel , S. 2005 . A novel family of glucosyl 1,5-anhydro-d-fructose derivatives synthesised by transglucosylation with dextransucrase fromLeuconostoc mesenteroides NRRL B-512F . Carbohydr. Res. , 340 ( 3 ) : 395 – 401 .
  • Demuth , K. , Jordening , H. J. and Buchholz , K. 2002 . Oligosaccharide synthesis by dextransucrase: new unconventional acceptors . Carbohydr. Res. , 337 ( 20 ) : 1811 – 1820 .
  • Cote , G. L. and Dunlap , C. A. 2003 . Alternansucrase acceptor reactions with methyl hexopyranosides . Carbohydr. Res. , 338 ( 19 ) : 1961 – 1967 .
  • Richard , G. , Morel , S. , Willemot , R. M. , Monsan , P. and Remaud-Simeon , M. 2003 . Glucosylation of alpha-butyl- and alpha-octyl-D-glucopyranosides by dextransucrase and alternansucrase from Leuconostoc mesenteroides . Carbohydr. Res. , 338 ( 9 ) : 855 – 864 .
  • Seo , E. S. , Lee , J. H. , Park , J. Y. , Kim , D. , Han , H. J. and Robyt , J. F. 2005 . Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction . J. Biotechnol. , 117 ( 1 ) : 31 – 38 .
  • Yoon , S. H. , Bruce Fulton , D. and Robyt , J. F. 2004 . Enzymatic synthesis of two salicin analogues by reaction of salicyl alcohol with Bacillus macerans cyclomaltodextrin glucanyltransferase and Leuconostoc mesenteroides B-742CB dextransucrase . Carbohydr. Res. , 339 ( 8 ) : 1517 – 1529 .
  • Meulenbeld , G. H. and Hartmans , S. 2000 . Transglycosylation by Streptococcus mutans GS-5 glucosyltransferase-D: acceptor specificity and engineering of reaction conditions . Biotechnol. Bioeng. , 70 ( 4 ) : 363 – 369 .
  • Meulenbeld , G. H. , Zuilhof , H. , van Veldhuizen , A. , van den Heuvel , R. H. and Hartmans , S. 1999 . Enhanced (+)-catechin transglucosylating activity of Streptococcus mutans GS-5 glucosyltransferase-D due to fructose removal . Appl. Environ. Microbiol. , 65 ( 9 ) : 4141 – 4147 .
  • Bertrand , A. , Morel , S. , Lefoulon , F. , Rolland , Y. , Monsan , P. and Remaud-Simeon , M. 2006 . Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents . Carbohydr. Res. , 341 ( 7 ) : 855 – 863 .
  • Moon , Y. H. , Lee , J. H. , Ahn , J. S. , Nam , S. H. , Oh , D. K. , Park , D. H. , Chung , H. J. , Kang , S. , Day , D. F. and Kim , D. 2006 . Synthesis, structure analyses, and characterization of novel epigallocatechin gallate (EGCG) glycosides using the glucansucrase from Leuconostoc mesenteroides B-1299CB . J. Agric. Food Chem. , 54 ( 4 ) : 1230 – 1237 .
  • Rainer , H. , Scharf , H.-D. and Runsink , J. 1992 . Reactions of partially acylated aldohexopyranosides, VIII. A new synthesis of the tetradeoxydisaccharide in avermectins . Liebigs Ann. Chem. , : 103 – 107 . (2)
  • Binkley , R. W. , Goewey , G. S. and Johnston , J. C. 1984 . Regioselective ring opening of selected benzylidene acetals: a photochemically inititated reaction for partial deprotection of carbohydrates . J. Org. Chem. , 49 : 992 – 996 .
  • Jensen , M. H. , Mirza , O. , Albenne , C. , Remaud-Simeon , M. , Monsan , P. , Gajhede , M. and Skov , L. K. 2004 . Crystal structure of the covalent intermediate of amylosucrase from Neisseria polysaccharea . Biochemistry , 43 ( 11 ) : 3104 – 3110 .
  • Mooser , G. , Hefta , S. A. , Paxton , R. J. , Shively , J. E. and Lee , T. D. 1991 . Isolation and sequence of an active-site peptide containing a catalytic aspartic acid from two Streptococcus sobrinus alpha-glucosyltransferases . J. Biol. Chem. , 266 ( 14 ) : 8916 – 8922 .
  • Mooser , G. and Iwaoka , K. R. 1989 . Sucrose 6-alpha-D-glucosyltransferase from Streptococcus sobrinus: characterization of a glucosyl-enzyme complex . Biochemistry , 28 ( 2 ) : 443 – 449 .
  • Moulis , C. , Arcache , A. , Escalier , P. C. , Rinaudo , M. , Monsan , P. , Remaud-Simeon , M. and Potocki-Veronese , G. 2006 . High-level production and purification of a fully active recombinant dextransucrase from Leuconostoc mesenteroides NRRL B-512F . FEMS Microbiol. Lett. , 261 ( 2 ) : 203 – 210 .
  • Moulis , C. , Joucla , G. , Harrison , D. , Fabre , E. , Potocki-Veronese , G. , Monsan , P. and Remaud-Simeon , M. 2006 . Understanding the polymerization mechanism of glycoside-hydrolase family 70 glucansucrases . J. Biol. Chem. , 281 ( 42 ) : 31254 – 31267 .
  • Joucla , G. , Pizzut , S. , Monsan , P. and Remaud-Simeon , M. 2006 . Construction of a fully active truncated alternansucrase partially deleted of its carboxy-terminal domain . FEBS Lett. , 580 ( 3 ) : 763 – 768 .
  • Koepsell , H. J. , Tsuchiya , H. M. , Hellman , N. N. , Kazenko , A. , Hoffman , C. A. , Sharpe , E. S. and Jackson , R. W. 1953 . Enzymatic synthesis of dextran; acceptor specificity and chain initiation . J Biol Chem. , 200 ( 2 ) : 793 – 801 .
  • Potocki de Montalk , G. , Remaud-Simeon , M. , Willemot , R. M. , Sarcabal , P. , Planchot , V. and Monsan , P. 2000 . Amylosucrase from Neisseria polysaccharea: novel catalytic properties . FEBS Lett. , 471 ( 2–3 ) : 219 – 223 .
  • Mulard , L. A. , Costachel , C. and Sansonetti , P. J. 2000 . Synthesis of the methyl glycosides of a di- and two trisaccharide fragments specific for the Shigella flexneri serotype 2a O-antigen . J. Carbohydr. Chem. , 19 ( 7 ) : 849 – 877 .
  • Lipkind , G. M. , Shashkov , A. S. , Nikolaev , A. V. , Mamyan , S. S. and Kochetkov , N. K. 1988 . Nuclear Overhauser effect and conformational states of 1- > 4 bound glucosylrhamnosides in queous solutions . Bioorg. Khim. , 13 ( 8 ) : 1081 – 1092 .
  • Bakinovskii , L. V. , Gomtsyan , A. R. , Bairamova , N. E. and Kochetkov , N. K. 1985 . Synthesis of oligosaccharide fragments of O-specific Shigella flexneri polysaccharides. II. Synthesis of trisaccharide Glc alpha1—3RHa alpha1—2Rha alpha1—OMe and tetrasaccharide GlcNAc beta1—2(Glc alpha1—3)Rha alpha1—2Rh alpha1—OMe . Bioorg. Khim. , 11 ( 2 ) : 254 – 263 .
  • Zou , W. , Brisson , J. R. , Yang , Q. L. , van der Zwan , M. and Jennings , H. J. 1996 . Synthesis and NMR assignment of two repeating units (decasaccharide) of the type III group B Streptococcus capsular polysaccharide and its 13C-labeled and N-propionyl substituted sialic acid analogues . Carbohydr. Res. , 295 : 209 – 228 .
  • Zou , W. , Li , J. , Larocque , S. and Jennings , H. J. 2001 . Construction of multivalent sialyl Le(x) from the type Ia group B Streptococcus capsular polysaccharide . Carbohydr. Res. , 332 ( 3 ) : 249 – 255 .
  • Yan , F. , Wakarchuk , W. W. , Gilbert , M. , Richards , J. C. and Whitfield , D. M. 2000 . Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide: a methodological comparison . Carbohydr. Res. , 328 ( 1 ) : 3 – 16 .
  • Joosten , J. A. , Kamerling , J. P. and Vliegenthart , J. F. 2003 . Chemo-enzymatic synthesis of a tetra- and octasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 14 . Carbohydr. Res. , 338 ( 23 ) : 2611 – 2627 .
  • Joosten , J. A. , Lazet , B. J. , Kamerling , J. P. and Vliegenthart , J. F. 2003 . Chemo-enzymatic synthesis of tetra-, penta-, and hexasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14 . Carbohydr. Res. , 338 ( 23 ) : 2629 – 2651 .
  • Niggemann , J. , Kamerling , J. P. and Vliegenthart , J. F. 1998 . beta-1,4-Galactosyltransferase-catalyzed synthesis of the branched tetrasaccharide repeating unit of Streptococcus pneumoniae type 14 . Bioorg. Med. Chem. , 6 ( 9 ) : 1605 – 1612 .
  • Rich , J. R. , Wakarchuk , W. W. and Bundle , D. R. 2006 . Chemical and chemoenzymatic synthesis of S-linked ganglioside analogues and their protein conjugates for use as immunogens . Chemistry , 12 ( 3 ) : 845 – 858 .
  • Lindberg , A. A. , Karnell , A. and Weintraub , A. 1991 . The lipopolysaccharide of Shigella bacteria as a virulence factor . Rev. Infect. Dis. , 13 ( Suppl 4 ) : S279 – 284 .
  • Adams , M. M. , Allison , G. E. and Verma , N. K. 2001 . Type IV O antigen modification genes in the genome of Shigella flexneri NCTC 8296 . Microbiology , 147 : 851 – 860 . (Pt 4)
  • Simmons , D. A. 1971 . Immunochemistry of Shigella flexneri O-antigens: a study of structural and genetic aspects of the biosynthesis of cell-surface antigens . Bacteriol. Rev. , 35 ( 2 ) : 117 – 148 .
  • Belot , F. , Guerreiro , C. , Baleux , F. and Mulard , L. A. 2005 . Synthesis of two linear PADRE conjugates bearing a deca- or pentadecasaccharide B epitope as potential synthetic vaccines against Shigella flexneri serotype 2a infection . Chemistry , 11 ( 5 ) : 1625 – 1635 .
  • Boutet , J. , Guerreiro , C. and Mulard , L. A. 2008 . Synthesis of branched tri- to pentasaccharides representative of fragments of Shigella flexneri serotypes 3a and/or X O-antigens . Tetrahedron , doi: 10.1016/j.tet.2008.08.080
  • Mulard , L. A. and Ughetto-Monfrin , J. 1999 . Synthesis of the methyl glycosides of a tri- and tetrasaccharide fragment specific for the Shigella flexneri serotype 5a O-antigen. A reinvestigation . J. Carbohydr. Chem. , 18 : 721 – 753 .
  • Mulard , L. A. and Ughetto-Monfrin , J. 2000 . First synthesis of a branched pentasaccharide representative of the repeating unit of the Shigella flexneri serotype 5a O-antigen . J. Carbohydr. Chem. , 19 : 193 – 220 .
  • Phalipon , A. , Costachel , C. , Grandjean , C. , Thuizat , A. , Guerreiro , C. , Tanguy , M. , Nato , F. , Vulliez-Le Normand , B. , Belot , F. , Wright , K. , Marcel-Peyre , V. , Sansonetti , P. J. and Mulard , L. A. 2006 . Characterization of functional oligosaccharide mimics of the Shigella flexneri serotype 2a O-antigen: implications for the development of a chemically defined glycoconjugate vaccine . J. Immunol. , 176 ( 3 ) : 1686 – 1694 .
  • Hayashi , M. , Tanaka , M. , Itoh , M. and Miyauchi , H. 1996 . A convenient and efficient synthesis of SLeX analogs . J. Org. Chem. , 61 ( 9 ) : 2938 – 2945 .
  • Mehta , S. , Gilbert , M. , Wakarchuk , W. W. and Whitfield , D. M. 2000 . Ready access to sialylated oligosaccharide donors . Org. Lett. , 2 ( 6 ) : 751 – 753 .
  • Yan , F. , Mehta , S. , Eichler , E. , Wakarchuk , W. W. , Gilbert , M. , Schur , M. J. and Whitfield , D. M. 2003 . Simplifying oligosaccharide synthesis: efficient synthesis of lactosamine and siaylated lactosamine oligosaccharide donors . J. Org. Chem. , 68 ( 6 ) : 2426 – 2431 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.