Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen


IMPACT FACTOR 2017: 5.294

CiteScore 2017: 3.42

SCImago Journal Rank (SJR) 2017: 1.212
Source Normalized Impact per Paper (SNIP) 2017: 1.546

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 79, Issue 12

Issues

Synthesis and biological relevance of N-acetylglucosamine-containing oligosaccharides

El Sayed H. El Ashry
  • Corresponding author
  • International Center for Chemical and Biological Sciences (HEJ Research Institute for Chemistry), Karachi University, Karachi, Pakistan
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Mohamed R. E. Aly
  • Corresponding author
  • Chemistry Department, Faculty of Science, Suez Canal University, Ismailia, Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200779122229

The structural diversity as well as the biological significance of N-acetylglucosamine-containing glycans are exemplified. The problem of forming the respective glycosidic bonds of synthetic targets is addressed. Special emphasis has been given to human milk oligosaccharides (HMOs), in view of their biological relevance, and synthetic approaches of selected examples are reported.

Keywords: dimethylmaleoyl; glycans; glycoconjugates; glycoforms; human milk oligosaccharides; N-acetylglucosamine; protecting groups

References

  • 1. (a)

    , A. Kobata. Proc. Jpn. Acad. 81B, 418 (2005);CrossrefGoogle Scholar

  • 1. (b)

    , C. R. Bertozzi, L. L. Kiessling. Science 291, 2357 (2001);CrossrefGoogle Scholar

  • 1. (c)

    , A. Helenius, M. Aebi. Science 291, 2364 (2001);CrossrefGoogle Scholar

  • 1. (d)

    , J. Alper. Science 291, 2338 (2001);CrossrefGoogle Scholar

  • 1. (e)

    J. C. McAuliffe, O. Hindsgaul. Chem. Ind. 170 (1997);Google Scholar

  • 1. (f)

    , E. F. Hounsel. Carbohydr. Res. 300, 47 (1997);CrossrefGoogle Scholar

  • 1. (g)

    , P. M. Simon. Drug Discov. Today 1, 522 (1996);CrossrefGoogle Scholar

  • 1. (h)

    , R. A. Dwek. Chem. Rev. 96, 683 (1996);CrossrefGoogle Scholar

  • 1. (i)

    , A. Varki. Glycobiology 3, 97 (1993);CrossrefGoogle Scholar

  • 1. (j)

    , A. Kobata. Acc. Chem. Res. 26, 319 (1993);CrossrefGoogle Scholar

  • 1. (k)

    , R. Kornfeld, S. Kornfeld. Ann. Rev. Biochem. 54, 631 (1985);CrossrefGoogle Scholar

  • 1. (l)

    , H. Herzner, T.Reipen, M. Schultz, H. Kunz. Chem. Rev. 100, 4495 (2000).CrossrefGoogle Scholar

  • 2.

    , G. Vaaje-Kolstad, A. Vasella, M. G. Peter, C. Netter, D. R. Houston, B. Westereng, B. Synstad, V. G. H. Eijsink, D. M. F. van Aalten. J. Biol. Chem. 279, 3612 (2004).CrossrefGoogle Scholar

  • 3. (a)

    , F. V. Rao, D. R. Houston, R. G. Boot, J. M. F. G. Aerts, S. Sakuda, D. M. F. van Aalten. J. Biol. Chem. 278, 20110 (2003);CrossrefGoogle Scholar

  • 3. (b)

    , N. Asano. Glycobiology 13, 93R (2003).CrossrefGoogle Scholar

  • 4.

    , F. V. Rao, O. A. Andersen, K. A. Vora, J. A. DeMartino, D. M. F. van Aalten. Chem. Biol. 12, 973 (2005).CrossrefGoogle Scholar

  • 5.

    , A. R. Yeager, N. S. Finney. J. Org. Chem. 69, 613 (2004).CrossrefGoogle Scholar

  • 6.

    , D. Hesek, M. Suvorov, K.-I. Morio, M. Lee, S. Brown, S. B. Vakulenko, S. Mobashery. J. Org. Chem. 69, 778 (2004).CrossrefGoogle Scholar

  • 7.

    , D. Hesek, M. Lee, K.-I. Morio, S. Mobashery. J. Org. Chem. 69, 2137 (2004).CrossrefGoogle Scholar

  • 8.

    , P. L. DeAngelis. J. Biol. Chem. 274, 26557 (1999).CrossrefGoogle Scholar

  • 9.

    , H. Takaku, H.-K. Ishida, M. Fujita, T. Inazu, H. Ishida, M. Kiso. Synlett 818 (2007).CrossrefGoogle Scholar

  • 10.

    , J.-C. Prome, J. Denarie, G. Truchet. Pure Appl. Chem. 70, 55 (1998).CrossrefGoogle Scholar

  • 11.

    , G. E. D. Oldroyd, R. M. Mitra, R. J. Wais, S. R. Long. Plant J. 28, 191 (2001).CrossrefGoogle Scholar

  • 12.

    N. V. Parasadarao, C. A. Wass, K. S. Kim. Infect. Immun. 64, 154 (1996).Google Scholar

  • 13.

    , M. R. E. Aly, P. Rochaix, M. Amessou, L. Johannes, J.-C. Florent. Carbohydr. Res. 341, 2026 (2006).CrossrefGoogle Scholar

  • 14.

    , J.-Q. Wang, X. Chen, W. Zhang, S. Zacharek, Y. C. Chen, P. G. Wang. J. Am. Chem. Soc. 121, 8174 (1999).CrossrefGoogle Scholar

  • 15.

    W. M. Watkins. Adv. Human Genet. 10, 1 (1980).Google Scholar

  • 16.

    M. Izawa, K. Kumamoto, C. Mitsuoka, A. Kanamori, K. Ohmori, H. Ishida, S. Nakamura, K.Kurata-Miura, K. Sasaki, T. Nishi, R. Kannagi. Cancer Res. 60, 1410 (2000).Google Scholar

  • 17.

    M. Ugorski, A. Laskowska. Acta Biochim. Pol. 49, 303 (2002).Google Scholar

  • 18.

    , K. D. Patel, S. L. Cuvelier, S. Wiehler. Semin. Immunol. 14, 73 (2002).CrossrefGoogle Scholar

  • 19.

    J. F. Kennedy, C. A. White. Bioactive Carbohydrates in Chemistry, Biochemistry and Biology, Ellis Horwood, Chichester (1983).Google Scholar

  • 20.

    , P. Chaturvedi, C. D. Warren, M. Altaye, A. L. Morrow, G. Ruiz-Palacios, L. K. Pickering, D. S. Newburg. Glycobiology 11, 365 (2001).CrossrefGoogle Scholar

  • 21.

    M. Gudiel-Urbano, I. Goni. Arch. Latinoam. Nutr. 51, 332 (2001).Google Scholar

  • 22.

    S. Martin-Sosa, M. J. Martin, L. A. Garcia-Pardo, P. Hueso. J. Dairy Sci. 86, 52 (2003).CrossrefGoogle Scholar

  • 23.

    P. McVeagh, J. B. Miller. J. Paediatr. Child Health 33, 281 (1997).Google Scholar

  • 24.

    M. B. F. Stepans, S. L. Wilhelm, M. Hertzog, T. K. C. Rodehorst, S. Blaney, B. Clemens, J. J. Polak III, D. S. Newburg. Breastfeeding Med. 1, 207 (2006) and refs. cited therein.Google Scholar

  • 25.

    L. Bode. J. Nutr. 136, 2127 (2006).Google Scholar

  • 26.

    M. B. Engfer, B. Stahl, B. Finke, G. Sawatzki, H. Daniel. Am. J. Clin. Nutr. 71, 1589 (2000).Google Scholar

  • 27.

    G. R. Gibson, M. Roberfroid. J. Nutr. 125, 1401 (1995).Google Scholar

  • 28.

    , G. V. Coppa, L. Zampini, T. Galeazzi, B. Facinelli, L. Ferrante, R. Capretti, G. Orazio. Pediatr. Res. 59, 377 (2006).CrossrefGoogle Scholar

  • 29.

    B. Wang, J. Brand-Miller, P. McVeagh, P. Petocz. Am. J. Clin. Nutr. 74, 510 (2001).CrossrefGoogle Scholar

  • 30.

    , L. Bode, J. Rudloff, C. Kunz, J. Strobel, N. Klein. J. Leukoc. Biol. 76, 820 (2004).CrossrefGoogle Scholar

  • 31. (a)

    , J. Banoub, P. Boullanger, D. Lafont. Chem. Rev. 92, 1167 (1992);CrossrefGoogle Scholar

  • 31. (b)

    J. Debenham, R.Rodebaugh, B. Fraser-Reid. Liebigs Ann. 791 (1997);CrossrefGoogle Scholar

  • 31. (c)

    G.-J. Boons. In Carbohydrate Chemistry, Blackie A & P, Glasgow (1998);Google Scholar

  • 31. (d)

    S. Hanessian. In Preparative Carbohydrate Chemistry, Marcel Dekker, New York (1997);Google Scholar

  • 31. (e)

    , A. F. G. Bongat, A. V. Demchenko. Carbohydr. Res. 342, 374 (2007);CrossrefGoogle Scholar

  • 31. (f)

    , S. E. Zurabyan, A. Ya. Khorlin. Russ. Chem. Rev. 43, 887 (1974).CrossrefGoogle Scholar

  • 32.

    , E. S. H. El Ashry, N. Rashed, E. S. I. Ibrahim. Curr. Org. Synth. 2, 175 (2005).CrossrefGoogle Scholar

  • 33.

    E. S. H. El Ashry, A. El Nemr. Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates, Blackwell, Oxford (2005).Web of ScienceCrossrefGoogle Scholar

  • 34.

    , R. R. Schmidt, J. Castro-Palomino, O. Retz. Pure Appl. Chem. 71, 729 (1999).CrossrefGoogle Scholar

  • 35.

    M. R. E. Aly, J. Castro-Palomino, E. I. Ibrahim, E. S. H. El Ashry, R. R. Schmidt. Eur. J. Org. Chem. 2305 (1998).CrossrefGoogle Scholar

  • 36.

    , M. R. E. Aly, E. I. Ibrahim, E. S. H. El Ashry, R. R. Schmidt. Carbohydr. Res. 316, 121 (1999).CrossrefGoogle Scholar

  • 37. (a)

    , M. R. E. Aly, E. I. Ibrahim, E. S. H. El Ashry, R. R. Schmidt. Eur. J. Org. Chem. 319 (2000);CrossrefGoogle Scholar

  • 37. (b)

    , M. R. E. Aly, E. I. Ibrahim, E. H. El Ashry, R. R. Schmidt. Carbohydr. Res. 331, 129 (2001).CrossrefGoogle Scholar

  • 38.

    , P. Knuhr, J.-C. Palomino, M. Grathwohl, R. R. Schmidt. Eur. J. Org. Chem. 4239 (2001).CrossrefGoogle Scholar

  • 39.

    , F. Roussel, M. Takhi, R. R. Schmidt. J. Org. Chem. 66, 8540 (2001).CrossrefGoogle Scholar

About the article

Published Online: 2009-01-01

Published in Print: 2007-01-01


Citation Information: Pure and Applied Chemistry, Volume 79, Issue 12, Pages 2229–2242, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200779122229.

Export Citation

© 2013 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Guillaume Despras, Dominique Urban, Boris Vauzeilles, and Jean-Marie Beau
Chem. Commun., 2014, Volume 50, Number 9, Page 1067
[2]
Ramu Enugala, Luísa C. R. Carvalho, Marina J. Dias Pires, and M. Manuel B. Marques
Chemistry - An Asian Journal, 2012, Volume 7, Number 11, Page 2482
[3]
Eduardo Reyes, María Alejandra Vitale, and Antonio Guerrero
Piel, 2012, Volume 27, Number 4, Page 218
[5]
El Sayed H. El‐Ashry, Nagwa Rashed, Laila F. Awad, El Sayed Ramadan, Somia M. Abdel‐Maggeed, and Nagat Rezki
Journal of Carbohydrate Chemistry, 2008, Volume 27, Number 2, Page 70
[6]
El Sayed H. El Ashry, Aly A. Aly, Mohamed R. Aouad, and Mohammed R. Amer
Nucleosides, Nucleotides and Nucleic Acids, 2010, Volume 29, Number 9, Page 698
[7]
Dusan Hesek, Mijoon Lee, Weilie Zhang, Bruce C. Noll, and Shahriar Mobashery
Journal of the American Chemical Society, 2009, Volume 131, Number 14, Page 5187
[8]
María I. Colombo, Edmundo A. Rúveda, and Carlos A. Stortz
Organic & Biomolecular Chemistry, 2011, Volume 9, Number 8, Page 3020

Comments (0)

Please log in or register to comment.
Log in