Dr Martina Lahmann

Image of Martina Lahmann
Name
Martina Lahmann
Position
Senior Lecturer in Organic Chemistry
Email
m.lahmann@bangor.ac.uk
Phone
+44 (0)1248 38 2390
Location
Chemistry Tower

Overview

Summary

Martina Lahmann is working at the Organic Chemistry/Life Science interface (Chemical Biology). Her expertise is in organic synthesis, carbohydrate and glycoconjugate chemistry.

http://bangor.academia.edu/MartinaLahmann

In depth

Martina received her diploma in Chemistry at the University of Hamburg, Germany, in 1994. She continued her work in the group of Prof. Joachim Thiem and obtained her Ph.D. in Organic Chemistry in 1997. Thereafter she moved to Stockholm University, Sweden, to work as a postdoc with Prof. Per J. Garegg and Prof. Stefan Oscarson. In 2002 she moved to Göteborg University, Sweden, to supervise the part of Stefan’s group which was relocated to Göteborg University and to lecture Organic Chemistry. In September 2005 she received the Docent degree in Organic Chemistry from Göteborg University. After a year in the Arrhenius Laboratory at Stockholm University, focussing on her research, Martina joined us at Bangor in September 2007.

The major focus on her current research comprises the development of new tools and structures for the identification and analysis of carbohydrate recognition domains, directing to a deeper understanding of carbohydrate-protein interactions on the molecular level, which eventually allows a more rational design and development of carbohydrate-based pharmaceuticals. Adhesion of bacteria to human glycoconjugate receptors is a crucial step in the development of many diseases and is often mediated by carbohydrate-protein interactions. As model system, she focuses on the binding of Helicobacter pylori (collaborators S. Oscarson, University College Dublin, and T. Borén, University of Umeå) which induces chronic inflammation by attaching itself to carbohydrate structures in the stomach lining. Another bacterial target is the uropathogenic Escherichia coli (UPEC), accounting for more than 80 % of urinary tract infections. To inhibit the adhesion of bacteria to the bladder is proposed to be an alternative approach to challenge antibiotic resistance. Transferred to the lab-bench this spans from “plain” oligosaccharide synthesis (e.g. Lewis-blood group structures), variously tagged carbohydrate structures (e.g. photolabeling, selenoglycosides) to designed conjugates (e.g. glycocluster, dendrimers).

The exploration of glycosylation reactions, e.g. solvent dependency, and the development of protecting group- and conjugation techniques represents another research-area.

Publications

Link to all Dr Lahmann’s publications on ResearcherID

(*corresponding author)

  1. Structural Insights into Polymorphic ABO Glycan Binding by Helicobacter pylori
    Author(s): Moonens, Kristof; Gideonsson, Paer; Subedi, Suresh; et al.
    Source: Cell Host & Microbe Volume: 19 Issue: 1 Pages: 55-66 Published: JAN 13 2016
    Times Cited: 1
    DOI: 10.1016/j.chom.2015.12.004
  2. Stereoselective Reduction Using Sodium Triacetoxyborodeuteride: Synthesis of Methyl 2,3-Di-O-benzyl-α-d-(4-2H)-glucopyranoside
    Author(s): Hani, Mobarak; Olof, Engström; Martina, Lahmann; et al.
    Source: Carbohydrate Chemistry Pages: 81-88 Published: 2015
    DOI: doi:10.1201/b18400-12 10.1201/b18400-12
  3. A Soluble Fucose-Specific Lectin from Aspergillus fumigatus Conidia - Structure, Specificity and Possible Role in Fungal Pathogenicity Josef Houser, Jan Komarek, Nikola Kostlanova, Gianluca Cioci, Annabelle Varrot, Sheena C. Kerr, Martina Lahmann, Viviane Balloy, John V. Fahy, Michel Chignard, Anne Imberty, and Michaela Wimmerova* PLoS One  8(12) (2013) e83077 doi:http://dx.doi.org/10.1371/journal.pone.0083077
  4. Lactosamine from lactulose via the Heyns rearrangement: a practical protocol
    Yulong Shan, Farah Oulaidi, Martina Lahmann*
    Tetrahedron Lett. 54 (30) (2013) 3960-3961.
    http://dx.doi.org/10.1016/j.tetlet.2013.05.086
  5. Multivalent glycoconjugates as anti-pathogenic agents.

    Anna Bernardi, Jesus Jiménez-Barbero, Alessandro Casnati, Cristina De Castro,
    Tamis Darbre, Franck Fieschi, Jukka Finne, Horst Funken, Karl-Erich Jaeger,
    Martina Lahmann, Thisbe K. Lindhorst, Marco Marradi, Paul Messner,
    Antonio Molinaro, Paul V. Murphy, Cristina Nativi, Stefan Oscarson,
    Soledad Penadés, Francesco Peri, Roland J. Pieters, Olivier Renaudet,
    Jean-Louis Reymond, Barbara Richichi, Javier Rojo, Francesco Sansone,
    Christina Schäffer, W. Bruce Turnbull, Trinidad Velasco-Torrijos, Sébastien Vidal,
    Stéphane Vincent, Tom Wennekes, Han Zuilhof and Anne Imberty*

    Chem. Soc. Rev. 42 (11) (2013) 4709-4727.
    doi: 10.1039/c2cs35408j

  6. The Tyrosine Gate as a Potential Entropic Lever in the Receptor-Binding Site of the Bacterial Adhesin FimH
    Adinda Wellens, Martina Lahmann, Mohamed Touaibia, Jonathan Vaucher, Stefan Oscarson, René Roy*, Han Remaut, and Julie Bouckaert*
    Biochemistry 51 (24) (2012) 4790-4799.
    doi: 10.1021/bi300251r
  7. Gold nanoparticles as carriers for a synthetic Streptococcus pneumoniae type 14 conjugate vaccine
    Dodi Safari , Marco Marradi, Fabrizio Chiodo, Huberta A Th Dekker, Yulong Shan, Roberto Adamo, Stefan Oscarson, Ger T Rijkers, Martina Lahmann, Johannis P Kamerling, Soledad Penadés*, Harm Snippe*
    Nanomedicine 7 (5) (2012) 651-662.
    doi:10.2217/nnm.11.151
  8. Transformations of chromanol and tocopherol and synthesis of ascorbate conjugates.
    Martina Lahmann, Joachim Thiem*
    Tetrahedron 67 (9) (2011) 1654-1664.
    doi:10.1016/j.tet.2010.12.066
  9. Glycocluster design for improved avidity and selectivity in blocking human lectin/plant toxin binding to glycoproteins and cells.
    Sabine André, Martina Lahmann, Hans-Joachim Gabius, Stefan Oscarson*
    Mol. Pharmaceutics 7 (2010) 2270-2279.
    doi: 10.1021/mp1002416
  10. Synthesis of the Lewis b pentasaccharide and a HSA-conjugate thereof.
    Viviane Fournière, Linnéa Skantz, Ferenc Sajtos, Stefan Oscarson*, Martina Lahmann*
    Tetrahedron 66 (39) (2010) 7850-7855.
    doi:10.1016/j.tet.2010.07.036
  11. Synthesis of 6-PEtN-b-D-GalpNAc-(1→6)-b-D-Galp-(1→4)-b-D-GlcpNAc-(1→3)-b-D-Galp-(1→4)-b-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof.
    Andreas Sundgren, Martina Lahmann, Stefan Oscarson*
    Beilstein J. Org. Chem. 6 (2010) 704-708.
    doi:10.1016/j.tet.2010.07.036
  12. A TNF-like Trimeric Lectin Domain from Burkholderia cenocepacia with Specificity for Fucosylated Human Histo-Blood Group Antigens.
    O. Sulák, G. Cioci, M. Delia, M. Lahmann, A. Varrot, A. Imberty*, M. Wimmerová*,
    Structure 10 (18) (2010) 59-72.
    doi: 10.1016/j.str.2009.10.021
  13. Reversible non-covalent derivatisation of carbon nanotubes with glycosides.
    Claes-Henrik Andersson, Martina Lahmann, Stefan Oscarson and Helena Grennberg*
    Soft Matter 5 (2009) 2713-2716.
    doi: 10.1039/b907791j

  14. Architectures of Multivalent Glycomimetics for Probing Carbohydrate-Lectin Interactions.
    Martina Lahmann
    Top. Curr. Chem. 288 (2009) 17-65.
    10.1007/128_2008_30
    In: "Glycoscience and Microbial Adhesion", Th. K. Lindhorst, St. Oscarson (Eds.), Springer, Berlin/Heidelberg 2009.

  15. Identification of the Smallest Structure Capable of Evoking Opsonophagocytic Antibodies against Streptococcus pneumoniae Type 14.
    Dodi Safari, Huberta A. Th. Dekker, John A. F. Joosten, Dirk Michalik, Adriana Carvalho de Souza, Roberto Adamo, Martina Lahmann, Andreas Sundgren, Stefan Oscarson, Johannis P. Kamerling, and Harm Snippe*
    Infect. Immun. 76 (10) (2008) 4615-4623.
    doi:10.1128/IAI.00472-08

  16. Stereoselective Glycosylations using a 2-N-acyl-2N,3O-oxazolidinone protected GlcNAc donor.
    Johan D. M. Olsson, Lars Eriksson, Martina Lahmann and Stefan Oscarson*
    J. Org. Chem. (2008), 73 (18) 7181-7188.
    doi: 10.1021/jo800971s

  17. Atomic mapping of the sugar interactions in one-site and two-site mutants of Cyanovirin-N by NMR spectroscopy.
    Corine Sandström*, Birgit Hakkarainen, Elena Matei, Anja Glinschert, Martina Lahmann, Stefan Oscarson, Lennart Kenne, Angela Gronenborn
    Biochemistry 47 (12) (2008) 3625-3635.

    http://0-dx.doi.org.unicat.bangor.ac.uk/10.1021/bi702200m

  18. NMR study of hydroxy protons of di- and trimannosides, substructures of Man-9.
    Birgit Hakkarainen, Lennart Kenne, Martina Lahmann, Stefan Oscarson and
    Corine Sandström*
    Magn. Reson. Chem.
    45 (12) (2007), 1076-1080.
    http://dx.doi.org/10.1002/mrc.2080

  19. Synthesis of urine drug metabolites: Glucuronic acid glycosides of phenol intermediates.
    Carl-Johan Arewång, Martina Lahmann, Stefan Oscarson and Anna-Karin Tidén*
    Carbohydr. Res. 342 (7)(2007), 970-974.
    doi:10.1016/j.carres.2007.01.014

  20. Synthesis of monodeoxy analogues of the trisaccharide a-D-Glcp-(1-3)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp recognised by Calreticulin/Calnexin.
    Emiliano Gemma, Martina Lahmann and Stefan Oscarson*
    Carbohydr. Res., 341 (10) (2006) 1533-1542.
    doi:10.1016/j.carres.2006.03.015

  21. b-Propeller Crystal Structure of Psathyrella velutina Lectin. An integrin-like fungal protein interacting with monosaccharides and calcium.
    Gianluca Cioci, Edward P. Mitchell, Valerie Chazalet, Henry Debray, Stefan Oscarson, Martina Lahmann, Christelle Breton, Catherine Gautier, Serge Perez and Anne Imberty*
    J. Mol. Biol., 357 (5) (2006) 1575-1591.
    doi:10.1016/j.jmb.2006.01.066  

  22. Synthesis of oligosaccharides corresponding to Vibrio cholerae O139 polysaccharide structures containing dideoxy sugars and a cyclic phosphate.
    Dominika Turek, Andreas Sundgren, Martina Lahmann and Stefan Oscarson*
    Org. Biomol. Chem., 4 (7) (2006) 1236-1241.
    doi:10.1039/b518125a

  23. Synthesis of the tetrasaccharide a-D-Glcp-(1-3)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp recognised by Calreticulin/Calnexin
    Emiliano Gemma, Martina Lahmann and Stefan Oscarson*
    Carbohydr. Res., 340 (16) (2005) 2558-2562.
    doi:10.1016/j.carres.2005.09.001

  24. Block synthesis of Streptococcus pneumoniae type 14 capsular polysaccharide structures.
    Andreas Sundgren, Martina Lahmann, Stefan Oscarson*
    J. Carbohydr. Chem. 24 (2005), 379-391.

  25. Impact of natural variation in bacterial F17G adhesins on crystallization behaviour.
    Lieven Buts, Adinda Wellens, Inge Van Molle, Lode Wyns, Remy Loris, Martina Lahmann, Stefan Oscarson, Henri De Greve and Julie Bouckaert*
    Acta Cryst. D61 (8) (2005) 1149-1159.

  26. The fucose-binding lectin from Ralstonia solanacearum: A new type of b-propeller architecture formed by oligomerisation and interacting with fucoside, fucosyllactose and plant xyloglucan
    Nikola Kostlanová, Edward P. Mitchell, Hugues Lortat-Jacob, Stefan Oscarson, Martina Lahmann, Nechama Gilboa-Garber, Gérard Chambat, Michaela Wimmerová* and Anne Imberty*
    J. Biol. Chem. 280 (30) (2005) 27839-27849.

  27. Ethyl 2-acetamido-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-thio-b-D-glycopyranoside as a versatile GlcNAc donor
    Mike Boysen, Emiliano Gemma, Martina Lahmann, Stefan Oscarson*
    Chem. Commun. 24 (2005) 3044-3046.
    doi:10.1039/b503651h

  28. Synthesis of the Lewis b hexasaccharide and HSA-conjugates thereof.
    Martina Lahmann*, Linnéa Bülow, Peter Teodorovic, Helena Gybäck, Stefan Oscarson
    Glycoconjugate J. 21 (5) (2004) 251-256.
    DOI: 10.1023/B:GLYC.0000045097.19353.73

  29. Ligands of the asialoglycoprotein receptor for targeted gene delivery, part 1: Synthesis of and binding studies with biotinylated cluster glycosides containing N-acetylgalactosamine.
    Ulrika Westerlind, Jacob Westman, Elisabeth Törnquist, C. I. Edvard Smith, Stefan Oscarson, Martina Lahmann, Thomas Norberg*
    Glycoconjugate J. 21 (5) (2004) 227-241.
    DOI: 10.1023/B:GLYC.0000045095.86867.c0

  30. Functional adaptation of BabA, the Helicobacter pylori ABO blood-group antigen binding adhesin.
    Marina Aspholm-Hurtig, Giedrius Dailide, Martina Lahmann, Awdhesh Kalia, Dag Ilver, Niamh Roche, Susanne Vikström, Rolf Sjöström, Sara Lindén, Anna Bäckström, Anna Arnqvist, Jafar Mahdavi, Ulf J. Nilsson, Billie Velapatiño, Robert H. Gilman, Markus Gerhard, Teresa Alarcon, Manuel López-Brea, Teruko Nakazawa, James G. Fox, Pelayo Correa, Maria Gloria Dominguez-Bello, Guillermo I Perez-Perez, Martin J. Blaser, Staffan Normark, Ingemar Carlstedt, Stefan Oscarson, Susann Teneberg*, Douglas E. Berg*, Thomas Borén*
    Science 305 (5683) (2004) 519-522.
    doi:10.1126/science.1098801

  31. Synthesis of urine drug metabolites: Glucuranosyl esters of carboxymefloquine, indoprofen, (S)-naproxen and desmethyl (S)-naproxen.
    Martina Lahmann*, Moa Andresen Bergström, Dominika Turek and Stefan Oscarson
    J. Carbohydr. Chem. 23 (2&3) (2004) 123-132.

  32. SmI2 /water/amine mediates cleavage of allyl ether protected alcohols — application in carbohydrate synthesis and mechanistic considerations.
    Anders Dahlén, Andreas Sundgren, Martina Lahmann, Stefan Oscarson and Göran Hilmersson*
    Org. Lett., 5 (22) (2003) 4085-4088.

  33. Synthesis of dihydrodiosgenine glycosides as mimetics of bidesmosidic steroidal saponins.
    René Suhr, Martina Lahmann, Stefan Oscarson, and Joachim Thiem*
    Eur. J. Org. Chem. 9 (20) (2003), 4003-4011.
    doi:10.1002/ejoc.200300290

  34. The fimbrial adhesion F17-G of enterotoxigenic Escherichia coli has an immunoglobulin-like lectin domain that binds N-acetylglucosamine.
    Lieven Buts, Julie Bouckaert, Erwin De Genst, Remy Loris, Stefan Oscarson, Martina Lahmann, Joris Messens, Elke Brosens, Lode Wyns and Henri De Greve*
    Mol. Microbiol. 49 (3) (2003) 705-716.
    doi:10.1046/j.1365-2958.2003.03600.x

  35. Solving the phase problem for carbohydrate-binding proteins using selenium derivatives of their ligands: a case study involving the bacterial F17-G adhesin.
    Lieven Buts*, Remy Loris, Erwin De Genst, Stefan Oscarson, Martina Lahmann,
    Joris Messens, Elke Brosens, Lode Wyns, Henri De Greve and Julie Bouckaert*
    Acta Cryst. D59 (6) (2003) 1012-1015.

  36. Design and synthesis of HIV-1 protease inhibitors. Novel tetrahydrofuran P2/P2’-groups interacting with Asp29/30 of the HIV-1 protease. Determination of binding from X-ray crystal structure of inhibitor protease complex.
    Karin Oscarsson, Martina Lahmann, Jimmy Lindberg, Jussi Kangasmetsä, Torsten Unge, Stefan Oscarson, Anders Hallberg, Bertil Samuelsson*,
    Bioorgan. Med. Chem. 11 (2003) 1107-1115.
    doi:10.1016/S0968-0896(02)00535-7 

  37. A facile approach to diosgenin and furostan type saponins bearing a 3b-chacotriose moiety.
    Martina Lahmann, Helena Gybäck, Per J. Garegg, Stefan Oscarson*,
    René Suhr, Joachim Thiem, Carbohydr. Res. 337 (2002) 2153-2159.
    doi:10.1016/S0008-6215(02)00275-6

  38. Investigation of the reactivity difference between thioglycoside donors with variant aglycon parts.
    Martina Lahmann and Stefan Oscarson*, Can. J. Chem. 80 (2002) 889-893.

  39. Synthesis of an highly differentially protected GPI-anchor skeleton.
    Martina Lahmann, Per J. Garegg, Peter Konradsson, and Stefan Oscarson*,
    Can. J. Chem. 80 (2002) 1105-1111.

  40. One-pot oligosaccharide synthesis exploiting solvent reactivity effects.
    Martina Lahmann, Stefan Oscarson*, Org. Lett., 2(24) (2000) 3881-3882.

  41. Darstellung von Tocopherol-Ascorbinsäure-Konjugaten.
    Martina Lahmann, Doctoral Thesis (1997) University of Hamburg, Hamburg, Germany.

  42. Synthesis of a-tocopheryl oligosaccharides.
    Joachim Thiem*, Martina Lahmann, Carbohydr. Res., 299 (1997) 23-31.
    doi:10.1016/S0008-6215(96)00331-X 

Research

Welcome to the Carbohydrate Lab!

In our laboratory almost everything orbits carbohydrates. Carbohydrates represent - also outside the lab - the most abundant family of nature products.

Everybody has probably heard about

  • their role as energy storage, e.g. as sucrose A - in everyday language just called ‘sugar’,
  • their capability supporting tissue in plants, e.g., cellulose B helps building up even the largest trees,
  • their ability in keeping many arthropods (as insects, spiders and crustaceans) protected in their sometimes pretty hard ‘skin’, e.g., the lobster’s shell consist mainly of a polysaccharide called chitin C.

Image of research

However, complex oligosaccharide structures are essential to get biological systems working and carbohydrate structures placed e.g. on the outside of a cell-wall can behave both as flypaper and as signpost for other bio molecules. Two examples:

  1. the “ABO-blood-groups” are assigned by carbohydrate structures present on the surface of (red blood) cells
  2. too old red blood cells are sorted out by the liver if they present too little sialic acids (certain carbohydrates) on their surface (because the red blood cells loose them when getting older)

As more as we understand the relevance of carbohydrates and their conjugates, the interest in possible pharmaceutical applications is growing (e.g. development of vaccines). However, compared to peptides the construction of oligosaccharides is not as automated and still often governed by ‘trial and error’.

At this point our research begins:

Our general aim is it to understand the chemistry of carbohydrates as much as possible by studying glycosylation reactions and the development of protecting group-techniques. By doing this, we produce many biologically interesting compounds which are further examined by biochemists and biologists. Since ‘naked’ oligosaccharides are usually too small to produce a response in a biological system, we have to ‘inflate’ them by connecting them to carrier, e.g. proteins. In other cases it is useful to bunch several copies of the carbohydrate structures together by preparing glycoclusters or glycodendrimers. Thus, conjugation of carbohydrate structures via various spacer molecules to a carrier is another area of our research.

Some introductionary reading:

Architectures of Multivalent Glycomimetics for Probing Carbohydrate-Lectin Interactions.
Martina Lahmann
Top. Curr. Chem. 288 (2009), 17-65.
10.1007/128_2008_30
In: "Glycoscience and Microbial Adhesion", Th. K. Lindhorst, St. Oscarson (Eds.), Springer, Berlin/Heidelberg 2009.

Group

Postdoctoral level

Dr Farah Oulaidi

Dr Mark Goodall

PhD students

Liam Nelligan

Liam did both his undergraduate studies and his MSc at the School of Chemistry. Liam joined the group in 2011 (KESS-funded).

Mark Long
Mark did his undergraduate studies at the School of Chemistry where he graduated in 2010 with a BSc (1st class). He did his final year project in our research group and decided to continue with sugar chemistry. Mark is currently finalising his research projects (KESS-funded).

Viviane Fournière

In November 2007, Viviane Fournière started her PhD studies in the carbohydrate group at the School of Chemistry. She received her Research Master’s degree in Organic and Bioorganic Chemistry from the Ecole nationale Supérieure de Chimie de Mulhouse in France. Viviane did her final undergraduate research project “Towards the synthesis of selenoether-bridged, non-glycosidically-linked pseudodisaccharides” under the supervision of docent Ian Cumpstey in 2007 at Stockholm University.

Vivane did her PhD studies part-time and shared her research with being a Senior Demonstrator at the School of Chemistry. In January 2012 Viviane successfully defended her PhD thesis with the title "Synthetic Tools for Carbohydrate-Protein Interaction Studies" (external: Prof Sabine Flitsch, Manchester/UK).

Abstract

Carbohydrate-protein interactions are important for the tuning of many biological processes. Tools are required to investigate the carbohydrate recognition domains. Several examples are presented in this work.

The first project consists in the synthesis of neoglycoconjugates for binding studies. Here a simple and efficient route to functionalise chitobiose, chitotriose and chitotetraose with a suitable linker avoiding protecting group chemistry is described. Unprotected chitooligomeres were used as starting material. After amination of the anomeric position of the saccharides, the linker was attached by amide formation. An amide bond was chosen to mimic the peptide bond. This linkage is also more stable than an amino linkage.

The second project discussesTwo projects discuss the synthesis of two Lewisb related oligosaccharides, a pentasaccharide and a heptasaccharide. Using as many identical building and reactions as possible in both the synthesis, the oligosaccharides was assembled following a linear pathway. For the pentasaccharide synthesis, a convergent pathway was attempted first. Starting respectively with a monosaccharide or a disaccharide, each sugar was added after the other, usually followed by a protecting group manipulation. Experience gained during the pentasaccharide synthesis for protecting group manipulation, strategic group pattern and glycosylation was used for the heptasaccharide synthesis. 1,2-cis glycosylation was improved via a new one-pot procedure. At the end, a hydrogenolysis provided the fully deprotected target molecule.

The third projectslast project deals with selenoglycosides. They are intended to improve structure elucidation of lectins by X-Ray crystallography.

Since both α and β selenoglycosides are of interest, a route to the two anomers using a common precursor was investigated. The β-selenoglycosides of common mono- and disaccharides were prepared. After protection by acetyl groups, theThe respective glycosyl halides were added to the “in situ” reduced dimethyldiselenide. The anomerisation of the β anomers were performed using BF3•OEt2. The esters were finally cleaved in basic medium by transesterification. This route was applied on a H1/Lewisb determinant as well. The major problem in this part of the project was to obtain the β orientation of the selenomethyl group without using a participating group. A solution was eventually found by employing a large excess of the reducing agent during the introduction of the seleno group as a smaller excess led to an α/β mixture.

Yulong Shan

In October 2008 Yulong Shan joined the group to carry out his PhD studies. Coming from a background in analytical chemistry, he worked on both analytical and synthetic carbohydrate chemistry. Yulong successfully defended his thesis in the beginning of 2012 (external: Prof Thomas Norberg, Uppsala/S).

Abstract

In this thesis four projects related to bioactive carbohydrates are described. The first project is about the extraction of iminosugars from Hyacinthoides non-scripta. This is the first time that extraction from English bluebell seeds has been described. Efficient extraction and isolation methods are reported. Another project discusses the development of a total synthetic carbohydrate conjugate vaccine candidate against Streptococcus pneumoniae type 14 using Gold nanoparticles as carrier. The synthetic pathway of the introduction of a linker for conjugation, and the deprotection of the tetrasaccharide corresponding to the repeating unit of the Streptococcus pneumoniae type 14 capsular polysaccharide is described. The biological results of the developed vaccine candidate are briefly discussed. In the third project, attempts to synthesise regioselectively sulfated disaccharides to be used in binding studies with FedF adhesin of E. coli are described. In this section, an improved high-yielding method based on the Heyns rearrangement for the synthesis of N-acetyl lactosamine (LacNAc) is also reported. In the fourth part, conjugation of the Lewis b hexasaccharide to be used for studies of Lewis b blood group antigen binding adhesin is reported.

Linnéa Skantz

Linnéa Skantz, b. Bülow, started her PhD studies in the end of 2003 at Göteborg University. In 2007 she defended her Licentiate thesis with the title “Synthesis of oligosaccharides of the Lewis blood group antigen family” at Stockholm University. After maternity leave Linnéa continued her research and on the 8th of May 2009 (Th K Lindhorst, faculty opponent) she defended her PhD thesis (Synthesis of biologically active oligosaccharides of the Lewis b family and investigations towards the synthesis of glycoclusters, abstract) at Stockholm University.