Bundle Research Group

2008

AICCS Annual Meeting Banff, Alberta - April 29-May 3
Synthesis of a Zwitterionic Hexasaccharide Containing two Repeating Units of the Streptococcus Pneumoniae Type 1 Capsular Polysaccharide Xiangyang Wu, Lina Cui, and David R. Bundle
Synthesis of Zwitterionic Oligosaccharides with the Potential to Stimulate T-Cell Responses Ithayavani Iynkkaran, Chang-Chung Ling, Xiangyang Wu and David. R. Bundle
The Convergent Synthesis of a-Galactosylceramide by Olefin Cross Metathesis Ye Cai and David R. Bundle
Synthesis of Oligosaccharide Fragments of Lipoarabinomannan from Mycobacterium Tuberculosis as Haptens for the Development of Anti-Tuberculosis Vaccines Yu Bai, Maju Joe, Jayant N. Tilekar and Todd L. Lowary
Design and Synthesis of Aspergillus fumigatus Antigens Vincent R. Bouvet, Feng Yang, Todd L. Lowary and David R. Bundle
Development of Glycoconjugate Polymeric Vaccines for the Treatment of Candida albicans Thanh Luu, Pavel I. Kitov, Tomasz Lipinski and David R. Bundle
Investigating synthetic techniques for a practical synthesis of ß-1,3 glucans as a preliminary backbone structure in a laminarin based glycan library J. James Bailey and David R. Bundle
In Vivo Synthesis of Complex Ganglioside Analogues by Metabolically Engineered Escherichia coli Strains Sandra Jacques, Chang-Chun Ling, Eric Samain, and David R. Bundle
Multifunctional Multivalency: Synthesis of Heterobifunctional Polymeric Shiga Toxin Antagonists for in vivo Evaluation P. I. Kitov, E. Paszkiewicz, Jared M. Jacobson, T. Lipinski and D. R. Bundle
Multifunctional Multivalency: Effect of Linker Length on the Activity of Heterobifunctional Polymeric Shiga Toxin Antagonists E. Paszkiewicz, P. I. Kitov, T. Lipinski and D. R. Bundle
Multifunctional Multivalency: The Synthesis of the Inactive Diastereoisomer of a Heterobifunctional Antagonist for Shiga Toxin Jared M. Jacobson, Eugenia Paskiewicz, Pavel I. Kitov and David R. Bundle
Multifunctional Multivalency: Synthesis of Polyvalent Heterobifunctional Ligand for Redirecting IgM to Siglec CD22 Lina Cui, Pavel I. Kitov, Gladys C. Completo, James C. Paulson, and David R. Bundle

2007

Gordon Conference on Carbohydrates Tilton, New Hampshire - June 17-22
Multifunctional Multivalency: Synthesis of Shiga Toxin Antagonists Based on Biocompatible N-(2-Hydroxypropyl) Methacrylamide (HPMA) Eugenia Paszkiewicz, Pavel I. Kitov, David R. Bundle
Chemical Mapping and STD NMR StudiesEstablish the Trichinella spiralis Epitope Recognized by a Monoclonal Antibody Lina Cui, Ping Zhang, Chang-Chun Ling and David Bundle
Multifunctional Multivalency: A Novel Concept Capable of Delivering One Billion Fold Avidity Gains Pavel Kitov, Dmitry Solomon, Tomasz Lipinski, Eugenia Paszkiewicz, Joanna Sadowska, George Mulvey, Glen Armstrong and David Bundle
Diversified Synthesisof Phytoshingosines and Glycocermide Analogs Ye Cai, Chang-Chun Ling and David Bundle
AICCS Annual Meeting Lake Louise, Alberta - May 3-5
Structure and Carbohydrate Binding Properties of Toxins A and B from Clostridium difficile Antonio Greco, Pavel Kitov, David Bundle, Jiangxiao Sun, John Klassen, Maja Rüpnik, Kenneth Ng
Multifunctional Multivalency: Design, Synthesis and Preliminary Evaluation of the Most Potent Shiga Toxin Inhibitor D. Solomon, P. I. Kitov, T. Lipinski, E. Paszkiewicz, J. M. Sadowska and D. R. Bundle
Multifunctional Multivalency: Synthesis of Shiga Toxin Antagonists Based on Biocompatible N-(2-Hydroxypropyl) Methacrylamide (HPMA) Eugenia Paszkiewicz, Pavel I. Kitov and David R. Bundle
Immuno-Targeting Malignant Cells Through Folate-GlcNAc Conjugated Ligands Lina Cui, Pavel Kitov and David R. Bundle
Synthesis of tailored conjugate vaccines composed of complex carbohydrate antigens and specific TH-cell peptide epitopes employing a novel linker methodology Sebastian Dziadek, Sandra Jacques and David R. Bundle
Immune Response to Small Oligosaccharide Enhanced by Copolymerization with Acrylamide T. Lipinski, P. Kitov, E. Paszkiewicz, X. Wu and D. R. Bundle
Synthesis and mapping of the protective epitope contained in di- and trisaccharide analogs of the (1-2)-ß-mannan from Candida albicans Corwin M. Nycholat, and David R. Bundle
Synthesis of Glycosphingolipid-Derivatives for the Therapy of Autoimmune Diseases Birgit Kranke and David R. Bundle
Diversified Synthesis of Phytosphingosines and Glycoceramide Analogs Ye Cai and David R. Bundle
Synthesis of ß-1,3 (laminarin) glucans as a preliminary backbone structure in a laminarin based glycan library J. James Bailey and David R. Bundle
Synthesis of the Zwitterionic Hexasaccharide Containing two Repeating Units of the Streptococcus pneumoniae Type 1 Capsular Polysaccharide Xiangyang Wu and David R. Bundle
Synthesis of Zwitterionic Oligosaccharides with the Potential to Stimulate T-Cell Responses Ithayavani Iynkkaran, Chang-Chung Ling and David R.Bundle
Synthesis of Pk-Trisaccharide Deoxy Analogs and Mapping of the Carbohydrate Binding sites in Shiga Toxins by FTICR Mass spectrometry Jonghwa Kim, Pavel Kitov and David R. Bundle
Affinities of Shiga Toxins 1 and 2 for Univalent and Oligovalent Pk Trisaccharide Analogs Measured by Electrospray Ionization Mass Spectrometry E. N. Kitova, P. I. Kitov, E. Paszkiewicz, J. Kim, G. L. Mulvey, G. D. Armstrong, D. R. Bundle and J. S. Klassen
Progress toward the Synthesis of Galactomannan Antigens of Aspergillus fumigatus Vincent R. Bouvet, Feng Yang, Todd L. Lowary and David R. Bundle

2006

Glycobiology 2006 Los Angeles, California - November
Heterobivalent Ligands: A Versatile Approach to Ligand-Induced Protein Aggregation Exemplified by the Structure-based Design of Shiga Toxin Antagonists Pavel I. Kitov and David R. Bundle

23rd International Carbohydrate Symposium Whistler, Canada - July 23-28
Synthetic Ganglioside Epitopes for Extracorporeal Removal of Antibodies in Neuropathy Birgit Kranke, Ping Zhang, Chang-Chun Ling, and David R. Bundle
A Facile Approach to 2-Acetamido-2-deoxy-ß-D-glucopyranosides Facilitates Convenient Syntheses of ?-Glycosides of Unusual Aminosugars Ye Cai, Chang-Chun Ling and David. R. Bundle
A Comparison of STD NMR and Chemical Mapping Studies of a Trichinella spiralis Antibody Binding Site Lina Cui, Chang-Chun Ling, David R. Bundle
Ganglioside Conjugate Vaccines Incorporating an in vivo-labile ß-Thiopropionate Tether S. Jacques, S. Dziadek, J. R. Rich, D. R. Bundle
Heterobivalent Ligand Mediated Ternary Complex Formation between Shiga Toxin and Serum Amyloid P Component P. I. Kitov, G. Grant, E. Paszkiewicz, J. Sadowska and D. R. Bundle
A Concise Chemoenzymatic Synthetic Route to Natural Gangliosides and Ganglioside Analogs for Cancer Immunotherapy Ping Zhang, Chang-Chun Ling, Sandra Jacques, Blake Zheng, and David R. Bundle
Synthesis of a Dimeric Heterobifunctional Ligand Designed to Induce a Complex Between Shiga Toxin and Serum Amyloid P Component D. Solomon, P. I. Kitov and D. R. Bundle
Immunochemistry of Thioanalogs of theTrisaccharide ß-Mannan Epitope of Candida Albicans T. Lipinski, X. Wu, E. Paszkiewicz and D.R. Bundle
Diastereoselective Synthesis of Phytosphingosine and Preparation of Thioanalogs of Galactosylceramide Chang-Chun Ling, Ye Cai, Ping Zhang, and David R. Bundle
Synthesis of the Trisaccharide Repeating Unit of the Type 1 Capsular Polysaccharide from Streptococcus Pneumoniae (Sp1) Xiangyang Wu and David R. Bundle
AICCS Annual Meeting Telus Centre, Edmonton, Alberta - June 8-9
Preliminary Steps Towards the Identification of ß-Mannopyranosyl Transferases from Candida albicans Magali Buffet and David Bundle
Synthesis of Glycoconjugate Vaccines on Clustered Modes against Candida Albicans Using a Novel Methodology Xiangyang Wu, Tomasz Lipinski, J. James Bailey, Frédéric Carrel and David Bundle
Immune Response to Thioanalogs of Trisaccharide Epitope of Candida Albicans ß-Mannan in Mice Tomasz Lipinski, Xiangyang Wu, Eugenia Paszkiewicz and David Bundle
Synthesis of disaccharide congeners of the (1-2)-ß-mannan from the cell-wall phosphomannan of Candida albicans Corwin Nycholat and David Bundle
Furanosyl Oxazoline of D-GlcNAc Functionalized at O-3: Larg-Scale Synthesis of ß-Glycosides of Unusual Aminosugars Ye Cai, Chang-Chun Ling and David Bundle
Efficient Synthesis of N-Acetylmuramic Acid and Muramyl Oligopeptide Immuno- adjuvants Ye Cai, Chang-Chun Ling and David Bundle
Diastereoselective Synthesis of Phytosphingosine and Preparation of Thioanalogs of Galactosylceramide Chang-Chun Ling, Ye Cai, Ping Zhang, and David Bundle
A Concise Chemoenzymatic Synthetic Route to Natural Gangliosides and Ganglioside Analogs for Cancer Immunotherapy Ping Zhang, Chang-Chun Ling, Sandra Jacques, Ruixiang Blake Zheng, and David Bundle
Ganglioside Conjugate Vaccines Incorporating an in vivo-labile ß-Thiopropionate Tether Sandra Jacques, Sebastian Dziadek, Jamie Rich, David Bundle
Synthesis of a Dimeric Heterobifunctional Ligand Designed to Induce a Complex Between Shiga Toxin and Serum Amyloid P Component Dmitry Solomon, Pavel Kitov and David Bundle
Heterobivalent Ligand Mediated Ternary Complex Formation between Shiga Toxin and Serum Amyloid P Component Pavel Kitov, Gordon Grant, Eugenia Paszkiewicz, Joanna Sadowska and David Bundle
American Society for Microbiology Denver, Colorado - March 13-17
A Synthetic Glycoconjugate Candida albicans Vaccine Confers Protection in a Disseminated Candidiasis Rabbit Model T. Lipinski, X. Wu, J. Sadowska, Y. Yasui, S. Cheriaparambil, R. P. Rennie, D. R. Bundle

2005

Gordon Conference on Carbohydrates Tilton, New Hampshire, June 19-24, 2005
Synthesis and Immunochemistry of Ganglioside Analogues Jacques, S.; Rich, J.R.; Bundle, D. R.
Synthesis of Multivalent Hetero-Bifunctional Inhibitors Dmitry Solomon, Eugenia Paszkiewicz, Pavel Kitov, Gordon A. Grant, and David R. Bundle
Evaluation of synthetic vaccine for Candida albicans Tomasz Lipinski, Xiangyang Wu, Joanna Sadowska, Shilton Cheriaparambil, Robert Rennie, and David R. Bundle
Single Site Functional Group Replacement and Tethering of Trisaccharides Yield Non-Linear Free Energy Gains Due to Changes in Bound Ligand Orientation McGavin, R.S., Peters, T. and Bundle, D.R.
Synthesis of Glycoconjugate Vaccines on Clustered Modes against Candida Albicans Using the Novel Methodology Xiangyang Wu, Tomasz Lipinski, J. James Bailey, Frédéric Carrel and David R. Bundle	PDF file
Single Site Functional Group Replacement and Thethering of Trisaccharides Yield Non-Linear Free Energy Gains Due to Changes in Bound Ligand Orientation Mc Gavin, R.S., Peters, T., and Bundle, D.R.	PDF file
Synthesis of Di- and Trisaccharide Congeners of the (1?2)-ß-Mannan from the Cell-wall Phosphomannanof Candida Albicans Corwin Nycholat and David R. Bundle	PDF file
88th Canadian Chemistry Conference and Exhibition Saskatoon, Saskatchewan, May 28-June 1, 2005
Synthesis and Immunochemistry of Ganglioside Analogues Jacques, S.; Rich, J.R.; Bundle, D. R.
A Facile Route To Unprotected b-Glycopyranosides Of N-Acetylglucosamine Via A Furanosyl Oxazoline Derivative Ye Cai, Chang-Chun Lin, David R. Bundle
An Iterative Approach to High Affinity Carbohydrate Ligand Design Lina Cui, C.-C. Ling and David R. Bundle
Synthesis of Di- and Trisaccharide Congeners of the (1-2)-ß-Mannan from the Cell-wall Phosphomannanof Candida Albicans Corwin Nycholat and David R. Bundle	PDF file
AICCS Annual Meeting and Symposium on Carbohydrate Science Lake Louise, Alberta, April 28-30, 2005
In-vitro Screening of Anti-adhesive Drugs that Complex with Serum Amyloid P Component to Inhibit Shiga-like Toxins Grant, G.A., Kitov, P.I, Solomon, D., Paszkiewicz, E., Sadowska, J.M, Mulvey, G.L., Armstrong, G.D., and Bundle, D.R..
Preliminary Comparison of the Epitope Maps of Ligands Directed Towards Monoclonal Antibody SYA/J6 McGavin, R.S., Peters, T. and Bundle, D.R.	PDF file
Synthesis of Multivalent Ligands directed against Anti-ganglioside Antibodies related to Autoimmune GBS Neuropathy Frédéric Carrel and David Bundle
Chemoenzymatic Synthesis of Functionalized Ganglioside Analogues Jacques, S.; Rich, J.R.; Bundle, D. R.
Synthesis of Multivalent Hetero-Bifunctional Inhibitors Dmitry Solomon, Eugenia Paszkiewicz, Pavel Kitov, Gordon A. Grant, and David R. Bundle
The Immune Response To Glycoconjugate Vaccines for Candida albicans and in vivo Protection Experiments in Neutropenic Rabbits Tomasz Lipinski, Joanna Sadowska, Shilton Cheriaparambil, Robert Rennie, and David R. Bundle
A Facile Route To Unprotected b-Glycopyranosides Of N-Acetylglucosamine Via A Furanosyl Oxazoline Derivative Ye Cai, Chuang-chun Lin, and David R. Bundle
A Novel Synthesis of Phytosphingosines from 6-Iodo Aminosugars Using a Zinc-mediated Reductive Elimination and Olefin Metathesis Ye Cai, Chuang-chun Lin, and David R. Bundle
Synthesis and Immunochemistry of S-Gangliosides Jamie R. Rich, Sandra Jacques and David R. Bundle
Synthesis of Glycoconjugate Vaccines against Candida albicans Using the Novel Linker Methodology Xiangyang Wu, J. James Bailey, Eugenia Paszkiewicz and David R. Bundle	PDF file
An Iterative Approach to High Affinity Carbohydrate Ligand Design Lina Cui, C.-C. Ling and David R. Bundle
Chemical and Chemo-Enzymatic Approach to the Synthesis of Pk-trisaccharide Deoxy Analogues Jonghwa Kim, Pavel Kitov and David R. Bundle	PDF file
Synthesis of Di- and Trisaccharide Congeners of the (1-2)-ß-Mannan from the Cell-wall Phosphomannanof Candida Albicans Corwin Nycholat and David R. Bundle
Synthesis of thio-analog of KRN7000 Chang-Chun Ling, Ping Zhang and David R. Bundle
Synthesis of Ganglioside Epitopes for Oligosaccharide Specific Immunoadsorption Therapy of GuillainBarré Syndrome Ping Zhang, Chang-Chun Ling, Kate Townson, Hugh J. Willison and David R. Bundle	PDF file

2004

International Carbohydrate Symposium
Glasgow, Scotland

Molecular Basis for Inhibition of Serum Amyloid P Component by New Multivalent Ligands

Pavel I. Kitov, Eugenia Paszkiewicz, Joanna Sadowska, David R. Bundle, Jason G.S. Ho, and Kenneth K.-S. Ng

Sulfur Linked Analogues of Gangliosides GM3 and GM2 for Use in Conjugate Vaccines

Jamie R. Rich, Sandra Jacques and David R. Bundle

PDF file (25k)

2003

Eurocarb Symposium 2003 Grenoble, France
Synthesis of Phosphmannan Antigens found in the Candida albicans cell wall Stéphane Chambert and David R. Bundle	PDF file (50k)
Synthesis and Binding Analysis of Cyclic Oligosaccharide Inhibitors of Monoclonal Antibody SYA/J6 Robert S. McGavin and David R. Bundle	PDF file (53k)
Understanding Neuropathy Pathogenesis: Synthesis of Ganglioside BSA Glycoconjugates and Immobilization on Sepharose Gel Soren Andersen, Chang-Chun Ling, Ping Zheng, Kate Townson, Jean Veitch, Hugh J. Willison, David R. Bundle	PDF file (35k)
Alberta Ingenuity Centre for Carbohydrate Science - Annual Meeting 2003 Edmonton, Alberta
An efficient route to sphinganine, phytosphingosine and their analogs Ye Cai, Chang-Chun Ling, and David R. Bundle	PDF file
Large Scale Synthesis of an Analog of Azidosphingosine and Preparation of the Corresponding GM2 Analog Chang-Chun Ling, Ping Zhang, Corwin M. Nycholat and David R. Bundle	PDF file
*Synthesis of Sulfur Containing Ganglioside Analogues for Use as Immunogens Jamie R. Rich, David R. Bundle	PDF file
*Synthesis and Binding Analysis of Cyclic Oligosaccharide Inhibitors of Monoclonal Antibody SYA/J6 Robert S. McGavin, and David R. Bundle	PDF file
*Chemical Synthesis and Adjuvant Properties of Gentiobiosyl Diphytanyl Glycerol Dean T. Williams and David R. Bundle	PDF file
*Towards the Total Synthesis of SB1a, a Carbohydrate Hapten Associated with Human Hepatocellular Carcinoma Dmitry Solomon and David R. Bundle	PDF file
Banff Symposium on Organic Chemistry 2003 Banff, Alberta
An efficient route to sphinganine, phytosphingosine and their analogs Ye Cai, Chang-Chun Ling, and David R. Bundle	PDF file

Annual Conference of the Society for Glycobiology
San Diego, CA. - Dec. 2003

Glycosyltransferase Catalyzed Synthesis of Thiooligosaccharides

Jamie R. Rich, Adam Szpacenko, Monica M. Palcic and David R. Bundle

PDF file (95k)

2002

International Carbohydrate Symposium Cairns, Australia; August 7-12 2002
Candida albicans b(1-2)-Mannans: Unique Solution Conformation and the Immune Response to Their Glycoconjugates. Mark Nitz, Chang-Chun Ling, Albin Otter, Joanna Sadowska and David R. Bundle	Poster Session I PP273 PDF file (203k)
Canadian Society for Chemistry Conference and Exhibition Vancouver, B.C., Canada; June 1-5, 2002
Intramolecular Pre-Organization of Oligosaccharides:The Synthesis of Cyclic Inhibitors Towards Monoclonal Antibody SYA/J6. Robert S. McGavin and David R. Bundle	PDF file (73k)
Synthetic Studies Toward Lewis Y Glycoconjugates. Lesley Liu, Chang-Chun Ling and David R. Bundle	PDF file (67k)
Thio-linked Oligosaccharides: Better Immunogens? Synthesis and Binding Studies of S-linked Trisaccharides Related to Shigella flexneri Variant Y LPS Antigens Henry N. Yu, Chang-Chun Ling and David R. Bundle	PDF file (75k)
Synthesis and conformational Studies of Ganglioside Analogues Containing S-linked Neuraminic Aicd and a S-linked Ceramide. J.R. Rich and D.R. Bundle	PDF file (62k)
Understanding Neuropathy Pathogenesis: Synthesis of Ganglioside BSA Glycoconjugates and Immobilization on Sepharose Gel Soren M. Andersen, Ping Zhang, Chang-Chun Ling and David R. Bundle	Lecture
Experimental NMR Conference 2002 Asilomar, California; April 14-19, 2002
Unique Helical Solution Confirmation in Candida albicans β1-2)-Mannopyranan Oligomers Albin Otter, Mark Nitz, Chang-Chun Ling and David R. Bundle	Lecture

2001

Gordon Research Conference - 2001 Tilton, NH
Determination of the Binding Affinity of mAb B3 for Synthetic Derivatives of Lewis Y Using FAC/MS Lesley Liu, Chang-Chun Ling and David R. Bundle	PDF file (82k)
Construction of 1-Thio-b-Mannopyranosyl and 1-Thio-b-Rhamnopyranosyl Linkages via a Facile S_N2 Reaction Henry N. Yu, Chang-Chun Ling and David R. Bundle	PDF file (76k)
Allyl Cleavage under Mild Oxidative Conditions Pavel I. Kitov and David R. Bundle	PDF file (407k)

2000

Experimental NMR Conference 2000 Asilomar, California; April 9-14, 2000
Conformational Analysis of a Tethered Disaccharide Trapped in the anit Conformation Shirley A. Wachowich-Sgarbi, Chang-Chun Ling, David R. Bundle and Albin Otter	PDF file (168k)
Canadian Bacterial Diseases Network Centre 2000
P^k-Starfish: The Next Generation P.I. Kitov, J.M. Sadowska, P. Marcato, G.D. Armstrong and D.R. Bundle	PDF file (281k)
Fourier-Transform Ion Cyclotron Resonance Mass Spectrometry Studies of the Homophilic Non-Covalent Interactions of Shiga-like Toxin Subunits, as well as their Interactions with Carbohydrate Ligands. E.N. Kitova, J.S. Klassen, P.I. Kitov, P. Marcatao, G.D. Armstrong and D.R. Bundle	PDF file (103k)

1999

Gordon Research Conference, Carbohydrates 1999

Rational Design of Soluable Sub-Nanomolar Inhibitors for Shiga Toxins

P.I. Kitov, J.M. Sadowska, D.R. Bundle, Randy J. Read and G.D Armstrong

PDF file (372k)