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Chemistry

Publications

60 Forman* A, Auzanneau F-I. (2016). Orthoesters Formation Leading to Mismatched Helfrich    Glycosylations at O-3 of N-trichloroacetylated Glucosamine Residues. Carbohydr Res, 425, 10–21.
 
59 Kamel Mousa W, Schwan A L, Davidson* J, Strange P, Liu L, Zhou T, Auzanneau FI, Raizada, M N.(2015). An Endophytic Fungus Isolated from Finger Millet (Eleucine coracona) Produces Anti-Fungal    Natural Products That Combat Pathogenic Fusarium Species. Frontiers. Frontiers Microbiol., 6 (1157).
 
58 Guillemineau* M, Lyczko J, Gabryelski W, Auzanneau F-I. (2015). Synthesis of Tumor-Associated LeALeX hexasaccharides: Instability of a Thiol containing oligosaccharide in Mass Spectrometry and Hyper-metalation detected by ESI FAIMS. J. Org. Chem., 80 (16), 8073–8083.
 
57 Kuir D, Guillemineau M, Auzanneau FI. (2015). Aggregation of a Tetrasaccharide Acceptor Observed by NMR: Synthesis of Pentasaccharide Fragments of the LeALeX Tumor-Associated Hexasaccharide. J. Org. Chem., 80, 5004−5013.
 
56 Singh, S. ; Su, Z.; Grossutti, M.;  Auzanneau, F.-I.* (2014) Attempts to prepare tethered bilayer lipid membranes using synthetic thioglycolipid anchors: synthesis of 6”-thiotrisaccharide glycolipid analogues and applications. Carbohydr. Res., 390, 50–58.
 
55 Jackson, T. A.; Robertson, V.; Auzanneau, F.-I.* (2014) Evidence for two populated conformations for the dimeric LeX and LeALeX tumor associated carbohydrate antigens. J. Med. Chem., 57 (3), 817–827
 
54 Moore, C.; Auzanneau, F.-I.* (2013) Understanding the recognition of Lewis X by anti-Lex monoclonal antibodies.  J. Med. Chem. 56 (20), 8183–8190.
 
53 Auzanneau, F.-I.; Borelli, S.; Pinto, B. M.* (2013) Synthesis and Immunological Activity of an Oligosaccharide-conjugate as a Vaccine Candidate Against Group A Streptococcus. Bioorg. Med. Chem. Lett., In press
 
52 Guillemineau, M.; Auzanneau, F.-I. (2012)
Challenging Deprotection Steps During the Synthesis of Tetra- and Pentasaccharide Fragments of the LeaLex Tumor-Associated Hexasaccharide Antigen. Accepted as a Featured Article  J. Org. Chem., 77, 8864–8878. (1 citation)
 
51 Auzanneau,* F.-I.; Jackson, T. A.; Liao, L. (2012)
Stochastic searches and NMR experiments on four Lewis A analogues: NMR experiments support some flexibility around the fucosidic bond. Bioorg. Med. Chem., 20, 5085–5093. (1 citation)
 
52 Guillemineau, M.; Auzanneau, F.-I. (2012)
Challenging Deprotection Steps During the Synthesis of Tetra- and Pentasaccharide Fragments of the LeaLex Tumor-Associated Hexasaccharide Antigen. J. Org. Chem., 77, 8864–8878, Featured article
 
51 Auzanneau,* F.-I.; Jackson, T. A.; Liao, L. (2012)
Stochastic searches and NMR experiments on four Lewis A analogues: NMR experiments support some flexibility around the fucosidic bond. Bioorg. Med. Chem., 20, 5085–5093.
 
50 Moore, C.; Auzanneau,* F.-I. (2012)
 Synthesis of 4” manipulated Lewis X trisaccharide analogues. Invited  to contribute to the Thematic series: Synthesis in the glycosciences II. Beilstein J. Org. Chem., 8, 1134–1143. DOI: 10.3762/bjoc.8.126
 
49 Zaccheus, M.; Pendrill, R.; Jackson, T. A., Wang, A.; Auzanneau, F.-I. Wildmalm, G.* (2012)
Conformational dynamics of a central trisaccharide fragment of the LeaLex tumor associated antigen studied by NMR spectroscopy and molecular dynamic simulations. Eur. J. Org. Chem., 4705–4715.
 
48 Guillemineau, M.; Auzanneau,* F.-I. (2012)
 Matched and Mismatched Acceptor/donor Pairs in the Glycosylation of a Trisaccharide Diol Free at O-3 of Two N-Acylated Glucosamine Residues. Carbohydr. Res., 357, 132–138.
 
47 Hendel, J.L .; Auzanneau,* F.-I. (2011)
 Convergent Preparation of DimLex Hexasaccharide Analogues. Eur. J. Org. Chem., 6864–6876. Selected cover picture Eur. J. Org. Chem. 2011, 6807
 
46 Guillemineau, M.; Singh, S.; Grossutti, M.; Auzanneau,* F.-I. (2010)
Synthesis of 6-thio pseudo glycolipids and their orientation on a gold slide studied by IRRAS. Carbohydr. Res., 345, 2723–2730 (NSERC)
 
45 Wang, J.-W.; Asnani, A.; Auzanneau,* F.-I. (2010)
Synthesis of a BSA-Lex glycoconjugate and recognition of Lex analogues by the anti-Lex Monoclonal antibody SH1: the identification of a non-cross reactive analogue. Bioorg. Med. Chem., 18, 7174–7185. (NSERC)
 
44 Wang, A.; Auzanneau,* F.-I. (2010)
Synthesis of LeaLex fragments and efficient one-step deprotection. Carbohydr. Res., 345, 1216–1221. (NSERC)
 
43 Wang, A.; Hendel, J. L.; Auzanneau,* F.-I. (2010)
Convergent syntheses of Lex analogues. Upon invitation by T. Lindhorst, Thematic series 7: Synthesis in the glycosciences. Beilstein J. Org. Chem., 6, article 17, 10 pages [doi:10.3762/bjoc.6.17 - published 22 Feb 2010]. (NSERC)
 
42 Hendel, J. L.; Wang, J-W.; Jackson, T. A.; Hardmeier, K.; De Los Santos, R.; Auzanneau, F.-I.* (2009)
How the Substituent at O-3 of N-Acetylglucosamine Impacts Glycosylation at O-4: A Comparative Study. J. Org. Chem., 74, 8321-8331. (NSERC)
 
41 Jackson, T. A.; Robertson, V.;  Imberty, A.; Auzanneau, F.-I.* (2009)
The flexibility of the LeaLex Tumor Associated Antigen central fragment studied by systematic and stochastic searches as well as dynamic simulations. Bioorg. Med. Chem.,17, 1514-1526. (NSERC)
 
40 Hendel, J. L.; Cheng, A.; Auzanneau, F.-I.* (2008)
Application and limitation of the methyl imidate protection strategy of N acetylglucosamine for glycosylations at O-4: Synthesis of Lewis A and Lewis X trisaccharide analogues. Carbohydr. Res. 343, 2914-2923. (NSERC, PREA)
 
39 Cheng, A. ; Hendel, J. L. ; Colangelo, K. ; Bonin, M. ; Auzanneau, F.-I. (2008)
Convenient Temporary Methyl Imidate Protection of N-Acetylglucosamine and Glycosylation at O-4. J. Org. Chem., 73, 7574-7579.
 
38 Asnani, A.; Auzanneau, F.-I. (2008)
Synthesis of Lewis X and three Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively. Carbohydr. Res., 343, 1653-1664.
 
37 Wang, A.; Auzanneau, F.-I. (2007)
Selective Protection Of 2-Azido-Lactose And In Situ Ferrier Rearrangement During Glycosylation: The Synthesis Of A Dimeric Lewis X Fragment. J. Org. Chem., 72, 3585-3588. (NSERC, World Bank)
 
36 Liao, L.; Auzanneau,* F.-I. (2006)
Synthesis of Lewis A trisaccharide analogues in which D-glucose and L-rhamnose replace D-galactose and L-fucose, respectively. Carbohydr. Res. 341, 2426-2433. (NSERC, Res. Corp., OGS)
 
35 Hand, C. E.; Auzanneau, F.-I.; Honek, J. F. (2006)
 Conformational analyses of mycothiol, a critical intracellular glycothiol in Mycobacteria. Carbohydr. Res. 341, 1164-1173.
 
34 Loureiro Morais, L.; Yuasa, H.; Bennis, K.; Ripoche,* I.; Auzanneau,* F.-I. (2006)
Chemoenzymatic synthesis of thio-nod factor intermediates: enzymatic transfer of glucosamine on thiochitobiose derivatives. Can. J. Chem., 84, 587-596. Invited to honor W. Szarek 65th birthday. (FCRF, NSERC, CFI/OIT).
 
33 Liao, L.; Robertson, V.; Auzanneau,* F.-I. (2005)
 Unusual conformational behavior of trisaccharides containing N-acetylglucosamine. Carbohydr. Res. 340, 2826-2832. (NSERC, Res. Corp., OGS)
 
32 Michon, F.; Moore, S.L.; Kim, J.; Blake, M.S.; Auzanneau, F.-I.; Johnston, B.D.; Johnson, M.A.; Pinto,* B.M. (2005)
The Doubly-Branched Hexasaccharide Epitope on the Cell-Wall Polysaccharide of Group A Streptococcus. Recognized by Human and Rabbit Antisera. Infect. Immun., 73, 6383-6389.
 
31 Liao, L.; Auzanneau,* F.-I. (2005)
The amide group in N-acetylgucosamine glycosyl acceptors affects glycosylation outcome. J. Org. Chem., 70, 6265-6273. (Res. Corp., CFI/OIT, NSERC).
 
30 Reid, C.W.; Blackburn, N.T.; Legaree, B.A.; Auzanneau, F.-I.; Clarke,* A.J. (2004) Inhibition of membrane-bound lytic transglycosylase B by NAG-thiazoline. FEBS Lett., 575, 73-79.
 
29 Liao, Liang; Auzanneau, F.-I. (2003)
Glycosylation of N-acetyl-glucosamine: Imidate Formation and Unexpected Conformation. Org. Let., 5, (2003) 2607-2610.
 
28 Loureiro Morais, L.; Bennis, K.; Ripoche, I.; Liao, L.; Auzanneau, F.-I.; Gelas, J. (2003)
Synthesis of S-linked thiooligosaccharides analogues of Nod factors. Part 3 [1]: synthesis of new protected thiodisaccharide and thiotrisaccharide intermediates. Carbohyd. Res., 308, 1369-1379.
 
27 Asnani, A; Auzanneau, F.-I. (2003)
Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively. Carbohyd. Res. , 308, 1045-1054.
 
26 Auzanneau, F.-I.; Sourial, E.; Schmidt J.M.; Feher, M. (2002)
Stochastic conformational search on the Lewis X (Lex) trisaccharide and three Lex analogues. Can. J. Chem., 80, 1088-1094.
 
25 Muñoz, J.L.; Gracía-Herrero, A.; Asensio, J.L.; Auzanneau, F.-I.; Cañada, F.J.; Jiménez-Barbero, J. (2001)
Conformational selection of non-hydrolyzable glycomimetics: the conformation of N,N’- diacetylthiochitobiose bound to wheat germ agglutinin. J. Chem. Soc., Perkin Tran. 1, 867-872.
 
24 Pitner, J.B.; Beyer, W.F.; Venetta, T.M.; Nycz, C.; Mitchell, M.J.; Harris, S.L.; Marino-Albernas, J.R.; Auzanneau, F.-I.; Forooghian, F.; Pinto, B.M. (2000)
Bivalency and Epitope Specificity of a High Affinity IgG3 Monoclonal Antibody to the Streptococcus group A Carbohydrate Antigen. Molecular Modeling of a Fv Fragment. Carbohydr. Res., 324, 17-29.
 
23 Auzanneau, F.-I.; Mialon, M.; Promé, D.; Promé, J.-C.; and Gelas, J. (1998)
Synthesis of S-linked thiooligosaccharide analogues of Nod factors. Part 2: Synthesis of an intermediate thiotrisaccharide. J. Org. Chem., 63, 6460-6465.
 
22 Auzanneau, F.-I.; Bennis, K.; Fanton, E.; Promé, D.; Defaye, J.; and Gelas, J. (1998)
Synthesis of S-linked thiooligosaccharide analogues of Nod factors. Part 1: Selectively N-protected 4-thiochitobiose precursors. J. Chem Soc. Perkin Trans. 1, 21, 3629-3636.
 
21 Auzanneau, F.-I.; Christensen, M.K.; Harris, S.L.; Meldal, M.; and Pinto, B.M. (1998)
Synthesis and characterization of polyethylene Glycol polyacrylamide copolymer (PEGA) resins containing carbohydrate ligands. Evaluation as supports for affinity chromatography. Can. J. Chem., 76, 1109-1118.
 
20 Wu X.; Mariño-Albernas, J.R.; Auzanneau, F.-I.; Verez-Bencomo, V.; and Pinto, B.M. (1998)
Synthesis and NMR analysis of 13C labeled oligosaccharides corresponding to the major glycolipid  from Mycobacterium leprae. Carbohydr. Res., 306, 493-503.
 
19 Harris, S.L.; Craig, L.; Mehroke, J.S.; Rashed, M.; Zwick, M.B.; Kenar, K.; Toone, E.J.; Greenspan, N.; Auzanneau, F.-I.; Mariño-Albernas, J.R.; Pinto, B.M.; and Scott, J.K. (1997)
Exploring the basis of peptide:carbohydrate cross-reactivity: Evidence for idiotype-specific recognition of anti-carbohydrate antibodies by peptides. Proc. Natl. Acad. Sci. USA., 94, 2454-2459.
 
18 Auzanneau, F.-I. and Pinto, B.M. (1996)
Preparation of antigens and immunoadsorbents corresponding to the Streptococcus group A cell-wall polysaccharide. Bioorg. Med. Chem., 4, 2003-2010.
 
17 Auzanneau, F.-I.; Forooghian, F.; and Pinto, B.M. (1996)
Efficient, convergent syntheses of oligosaccharide allylglycosides corresponding to the Streptococcus group A cell-wall polysaccharide. Carbohydr. Res., 291, 21-41.
 
16 Auzanneau, F.-I.; Meldal, M.; and Bock, K. (1995)
Synthesis, characterization and biocompatibility of PEGA resins. J. Peptide Sci., 1, 31-44.
 
15 Meldal, M.; Auzanneau, F.-I.; Hindsgaul, O.; and Palcic, M.M. (1994)
A PEGA resin for use in the solid phase chemical/enzymatic synthesis of glycopeptides. J. Chem Soc., Chem. Commun., 1849-1850.
 
14 Meldal, M.; Svendsen, I.; Breddam, K.; and Auzanneau, F.-I. (1994)
Portion-mixing subsite libraries of quenched fluorogenic substrates for complete mapping of endoprotease specificity. Proc. Natl. Acad. Sci. USA, 91, 3314-3318.
 
13 Bundle, D.R.; Altman, E.; Auzanneau, F.-I,; Baumann, H.; Eichler, E.; and Sigurskjold, B.W. (1994)
The structure of oligosaccharide-antibody complexes and improved inhibitors of carbohydrate-protein binding. 1994, Complex Carbohydrates In Drug Research; Structural and Functional Aspects, Ed: K.Bock, H.Clausen,  Munksgaard, Copenhagen, 36, 168-181.
 
12 Auzanneau, F.-I. and Bundle, D.R. (1993)
Synthesis of chloro-deoxy-trisaccharides related to the Shigella flexneri Y polysaccharide. Carbohydr. Res., 247, 195-209.
 
11 Auzanneau, F.-I. and Bundle, D.R. (1993)
Application of thioglycoside chemistry for the synthesis of trisaccharides and deoxy trisaccharides related to the Shigella flexneri Y polysaccharide. Can. J. Chem., 71, 534-548.
 
10 Auzanneau, F.-I.; Hanna, H.R.; and Bundle, D.R. (1993)
Synthesis of chemically modified disaccharide derivatives of the Shigella flexneri Y polysaccharide antigen. Carbohydr. Res., 240, 161-181.
 
9 Auzanneau, F.-I.; Mondange, M.; Charon, D.; and Szabo L. (1992)
  Chemistry of Bacterial endotoxins. Part 8. Synthesis of allyl 6-O-(3-deoxy-a-, and b-D-manno-oct-2-ulopyranosylonic acid)-2-deoxy-[(3R)-3-hydroxytetradecanamido]-b-D-glucopyranoside 4-phosphate and of the copolymer of the a- anomer with acrylamide. Carbohydr. Res., 228, 37-45.
 
8 Auzanneau, F.-I. and Bundle, D.R. (1991)
Incidence and avoidance of stereospecific 1,2 thioethyl migration during the synthesis of ethyl 1-thio-?-L-rhamnopyranoside 2,3-orthoester. Carbohydr. Res., 212, 13-24.
 
7 Auzanneau, F.-I.; Charon, D.; Szilagyi, L.; and Szabo, L. (1991)
Chemistry of bacterial endotoxins. Part 6. Synthesis of [allyl 5-O-(a-D-mannopyranosyl)-3-deoxy-a-D- manno-2-octulopyranosid]onic acid and of [allyl 5-O-(a-D-mannopyranosyl)-3-deoxy-a-D-manno- 2-octulopyranosid] onic acid 4-phosphate. J. Chem. Soc. Perkin Trans. 1, 803-809.
 
6 Auzanneau, F.-I.; Charon, D.; and Szabo, L. (1991)
Phosphorylated sugars. Part. 27. Synthesis and reaction in acidic medium of 5-O-substituted methyl 3-deoxy-a-D-manno-2-octulopyranosidonic acid 4-phosphate. J. Chem. Soc. Perkin Trans., 1, 509-517.
 
5 Auzanneau, F.-I.; Charon, D.; and Szabo, L. (1990)
Phosphorylated sugars. Part. 26. Synthesis of 3-deoxy-D-manno-2-octulosonic acid 7-phosphate. J. Chem. Soc. Perkin Trans., 1, 2831-2834.
 
4 Tahri-Jouti, M.-A.; Mondange, M.; Le Dur, A.; Auzanneau, F.-I.; Girard, R.; and Chaby, R. (1990)
Specific binding of lipopolysaccharides to mouse macrophages. II. Involvement of dinstinct lipid A substructures. Mol. Immunol., 27, 763-770.
 
3 Auzanneau, F.-I.; Charon, D.; and Szabo, L. (1990)
Formation of methyl (2,7-anhydro-3-deoxy-a-D-manno-2-octulofuranos)onate upon methanolysis of methyl (2,4,7,8-tetra-O-acetyl-3-deoxy-a-D-manno-2-octulo-pyranosid)onate. Carbohydr.Res., 201, 337-341.
 
2 Auzanneau, F.-I.; Charon, D.; Szabo, L.; and Mérienne, C. (1988)
Chemistry of bacterial endotoxins. Part 5. Synthesis of 1,5 lactones of 3-deoxy-D-manno-2-octulopyranosonic acid. Carbohydr. Res., 179, 125-136.
 
1 Charon, D.; Auzanneau, F.-I.; Mérienne, C.; and Szabo, L. (1987)
Formation of 1,5-lactones from 3-deoxy-D-manno-2-octulosonic acid. Tetrahedron Lett., 1393-1397.

Proceedings

Meldal, M.; Auzanneau, F.-I.; and Bock, K.
PEGA, characterization and application of a new type of resin for peptide and glycopeptide synthesis. Innovation and Perspectives in Solid Phase Synthesis, Biological and Biomedical Applications. Ed.: R. Epton 1994, 259-266.