Mechanisms of depolymerization and activation of a polysialic acid and its tetramer by hydrogen peroxide

Carbohydrate Polymers

Volumn 115, Issue , 2015, Pages 494-501

  Neyra, C ^a   Paladino, J ^a   Le Borgne, M ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Activation; Depolymerization; Hydrogen peroxide; Polysialic acid; Tetrasialic acid

Indexed keywords

DEPOLYMERIZATION; HYDROGEN PEROXIDE;

POLYSIALIC ACID; TETRAMERS;

CHEMICAL ACTIVATION;

HYDROGEN PEROXIDE; POLYSIALIC ACID; SIALIC ACID DERIVATIVE;

CHEMISTRY; OXIDATION REDUCTION REACTION; POLYMERIZATION;

HYDROGEN PEROXIDE; OXIDATION-REDUCTION; POLYMERIZATION; SIALIC ACIDS;

EID: 84907546153     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2014.08.112     Document Type: Article

References (20)

1. G.T. Barry Colominic acid, a polymer of N-acetylneuraminic acid The Journal of Experimental Medicine 107 4 1958 507 521
2. M. Bröker, P.M. Dull, R. Rappuoli, and P. Costantino Chemistry of a new investigational quadrivalent meningococcal conjugate vaccine that is immunogenic at all ages Vaccine 27 41 2009 5574 5580 10.1016/j.vaccine.2009.07.036
3. P. Costantino, F. Norelli, A. Giannozzi, S. D'Ascenzi, A. Bartoloni, and S. Kaur Size fractionation of bacterial capsular polysaccharides for their use in conjugate vaccines Vaccine 17 9-10 1999 1251 1263 10.1016/S0264-410X(98)00348-X
4. M. Cuello, O. Cabrera, I. Martinez, J.M. del Campo, M.A. Camaraza, and F. Sotolongo New meningococcal C polysaccharide-tetanus toxoid conjugate: Physico-chemical and immunological characterization Vaccine 25 10 2007 1798 1805 10.1016/j.vaccine.2006.11.029
5. J. Finne, U. Finne, H. Deagostini-Bazin, and C. Goridis Occurrence of α2 - 8 linked polysialosyl units in a neural cell adhesion molecule Biochemical and Biophysical Research Communications 112 2 1983 482 487 10.1016/0006-291X(83)91490-0
6. G. Gregoriadis, S. Jain, I. Papaioannou, and P. Laing Improving the therapeutic efficacy of peptides and proteins: A role for polysialic acids International Journal of Pharmaceutics 300 1-2 2005 125 130 10.1016/j.ijpharm.2005.06.007
7. K. Higashi, S. Hosoyama, A. Ohno, S. Masuko, B. Yang, and E. Sterner Photochemical preparation of a novel low molecular weight heparin Carbohydrate Polymers 87 2 2012 1737 1743 10.1016/j.carbpol.2011.09.087
8. R. Iijima, H. Takahashi, S. Ikegami, and M. Yamazaki Characterization of the reaction between sialic acid (N-acetylneuraminic acid) and hydrogen peroxide Biological and Pharmaceutical Bulletin 30 3 2007 580 582
9. R. Iijima, H. Takahashi, R. Namme, S. Ikegami, and M. Yamazaki Novel biological function of sialic acid (N-acetylneuraminic acid) as a hydrogen peroxide scavenger FEBS Letters 561 1-3 2004 163 166 10.1016/S0014-5793(04)00164-4
10. H.J. Jennings, and A.K. Bhattacharjee Isolation of 9-O-(α-d-N-acetylneuraminyl)-β-d-N-acetylneuraminic acid by partial acid hydrolysis, and its characterisation by 13 C N.M.R. Carbohydrate Research 55 1 1977 105 112 10.1016/S0008-6215(00)84447-X
11. C. Klein-Koerkamp, R. Granet, R. Zerrouki, N. Villandier, F. Jérôme, and J. Barrault Efficient oxidative modification of polysaccharides in water using H2O2 activated by iron sulfophthalocyanine Carbohydrate Polymers 78 4 2009 938 944 10.1016/j.carbpol.2009.07.021
12. X. Lemercinier, and C. Jones Full 1H NMR assignment and detailed O-acetylation patterns of capsular polysaccharides from Neisseria meningitidis used in vaccine production Carbohydrate Research 296 1-4 1996 83 96 10.1016/S0008-6215(96)00253-4
13. L. Li, Y. Abe, K. Kanagawa, T. Shoji, T. Mashino, and M. Mochizuki Iron-chelating agents never suppress Fenton reaction but participate in quenching spin-trapped radicals Analytica Chimica Acta 599 2 2007 315 319 10.1016/j.aca.2007.08.008
14. M.R. Lifely, U.T. Nowicka, and C. Moreno Analysis of the chain length of oligomers and polymers of sialic acid isolated from Neisseria meningitidis group B and C and Escherichia coli K1 and K92 Carbohydrate Research 156 1986 123 135 10.1016/S0008-6215(00)90104-6
15. A.A. Lindberg Glycoprotein conjugate vaccines Vaccine 17 Suppl 2 1999 S28 S36
16. A.E. Manzi, H.H. Higa, S. Diaz, and A. Varki Intramolecular self-cleavage of polysialic acid Journal of Biological Chemistry 269 38 1994 23617 23624
17. M. Mühlenhoff, M. Eckhardt, and R. Gerardy-Schahn Polysialic acid: Three-dimensional structure, biosynthesis and function Current Opinion in Structural Biology 8 5 1998 558 564 10.1016/S0959-440X(98)80144-9
18. C. Neyra, J. Paladino, and M. Le Borgne Oxidation of sialic acid using hydrogen peroxide as a new method to tune the reducing activity Carbohydrate Research 386 2014 92 98 10.1016/j.carres.2014.01.007
19. Ryall, R.P. (29 October 2003). Multivalent meningococcal polysaccharide-protein conjugate vaccine. European Patent 2003707551.
20. M. Wu, S. Xu, J. Zhao, H. Kang, and H. Ding Free-radical depolymerization of glycosaminoglycan from sea cucumber Thelenata ananas by hydrogen peroxide and copper ions Carbohydrate Polymers 80 4 2010 1116 1124 10.1016/j.carbpol.2010.01.032