Abstract
Bacillus anthracis is a Gram-positive, spore-forming soil bacterium that is closely related to Bacillus cereus and Bacillus thuringiensis. Infections with Bacillus anthracis result in a disease called anthrax (Mock and Fouet 2001; Sylvestre et al. 2002). Anthrax is primarily an infection of grazing cattle. Ingested spores germinate within the host to the vegetative form. Vegetative cells multiply, disseminate in the host organism, and kill the host by their virulence factors. Upon contact with air and depending on other environmental factors, the vegetative cells start to sporulate to form the dormant, durable spores again. B. anthracis spores are remarkably resistant to physical stress such as extreme temperatures, radiation, harsh chemicals, desiccation, and physical damage. These properties allow them to persist in the soil for decades (Nicholson et al. 2000). Human anthrax infections are very rare and only occur when humans are closely exposed to infected animals, tissue from infected animals or when they are directly exposed to B. anthracis spores (Quinn and Turnbull 1998). Depending on the route of infection, anthrax can occur in three forms: cutaneous, gastrointestinal or inhalation anthrax.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Adamo R, Saksena R, Kováč P (2005) Synthesis of the beta anomer of the spacer-equipped tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium. Carbohydr Res 340:2579–2582
Beatty ME, Ashford DA, Griffin PM, Tuxe RV, Sobel J (2003) Gastrointestinal anthrax: review of the literature. Arch Intern Med 163:2527–2531
Brachman PS, Gold H, Plotkin SA, Fekety FR, Werrin M, Ingraham NR (1962) Field evaluation of a human anthrax vaccine. Am J Public Health Nations Health 52:632–645
Carpino LA, El-Faham A (1995) Efficiency in peptide coupling: 1-hydroxy-7-azabenzotriazole vs 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine. J Org Chem 60:3561–3564
Choudhury B, Leoff C, Saile E, Wilkins P, Quinn CP, Kannenberg EL, Carlson RW (2006) The structure of the major cell wall polysaccharide of Bacillus anthracis is species-specific. J Biol Chem 281:27932–27941
Crich D, Vinogradova O (2007) Synthesis of the antigenic tetrasaccharide side chain from the major glycoprotein of Bacillus anthracis exosporium. J Org Chem 72:6513–6520
Daubenspeck JM, Zeng H, Chen P, Dong S, Steichen CT, Krishna NR, Pritchard DG, Turnbough CL Jr (2004) Novel oligosaccharide side chains of the collagen-like region of BclA, the major glycoprotein of the Bacillus anthracis exosporium. J Biol Chem 279:30945–30953
Dong S, McPherson SA, Tan L, Chesnokova ON, Turnbough CL Jr, Pritchard DG (2008) Anthrose biosynthetic operon of Bacillus anthracis. J Bacteriol 190:2350–2359
Food and Drug Administration (2005) 21 CFR Parts 201 and 610. Biological products; bacterial vaccines and toxoids; implementation of efficacy review; anthrax vaccine adsorbed; final order. Federal Register 70:75180–75198
Fürstner A, Müller T (1999) Efficient total synthesis of resin glycosides and analogues by ring-closing olefin methathesis. J Am Chem Soc 121:7814–7821
Golik J, Wong H, Krishnan B, Vyas DM, Doyle TW (1991) Stereochemical studies on esperamicins: determination of the absolute configuration of hydroxyamino sugar fragment. Tetrahedron Lett 32:1851–1854
Guo H, O’Doherty GA (2007a) De Novo asymmetric synthesis of the anthrax tetrasaccharide by a palladium-catalyzed glycosylation reaction. Angew Chem Int Ed 46:5206–5208
Guo H, O’Doherty GA (2007b) De Novo asymmetric synthesis of anthrax tetrrasaccharide and related tetrasaccharide. J Org Chem 73:5211–5220
Kuehn A, Kováč P, Saksena R, Bannert N, Klee SR, Ranisch H, Grunow R (2009) Development of antibodies against anthrose tetrasaccharide for specific detection of Bacillus anthracis spores. Clin Vaccine Immunol 16:1728–1737
Lucez D (2005) Bacillus anthracis (anthrax). In: Mandell G, Bennett J, Dolin R (eds) Mandell, Douglas, and Bennett’s principles and practice of infectious disease. Churchill Livingstone, Philadelphia, pp 2485–2491
Mehta AS, Saile E, Zhong W, Buskas T, Carlson R, Kannenberg E, Reed Y, Quinn CP, Boons GJ (2006) Synthesis and antigenic analysis of the BclA glycoprotein oligosaccharide from the Bacillus anthracis exosporium. Chem Eur J 12:9136–9149
Meyer M, Meyer B (1999) Characterization of ligand binding by saturation transfer difference NMR spectroscopy. Angew Chem Int Ed 38:1784–1788
Meyer B, Peters T (2003) NMR spectroscopy techniques for screening and identifying ligand binding to protein receptors. Angew Chem Int Ed 42:864–890
Moayeri M, Leppla SH (2004) The roles of anthrax toxin in pathogenesis. Curr Opin Microbiol 7:19–24
Mock M, Fouet A (2001) Anthrax. Annu Rev Microbiol 55:647–671
Nicholson WL, Munakata N, Horneck G, Melosh HJ, Setlow P (2000) Resistance of Bacillus endospores to extrem terrestrial and extraterrestrial environments. Microbiol Mol Biol Rev 64:548–572
Oberli MA, Bindschädler P, Werz DB, Seeberger PH (2008) Synthesis of a hexasaccharide repeating unit from Bacillus anthracis vegetative cell walls. Org Lett 10:905–908
Oberli MA, Tamorrini M, Tsai YH, Werz DB, Horlacher T, Adibekian A, Gauss D, Möller HM, Pluschke G, Seeberger PH (2010) Molecular analysis of carbohydrate-antibody interactions: a case study using a B. anthracis tetrasaccharide. J Am Chem Soc 132:10239–10241
Pasteur L (1881) De l’attenuation des virus et de leur retour à la virulence. Acad Sci Agric Bulg 92:429–435
Quinn C, Turnbull P (1998) Anthrax. In: Collier L, Balows A, Sussman M (eds) Topley & Wilson’s microbiology and microbial infections, 9th edn. Arnold/Oxford University Press, London/New York, pp 799–818
Raguputhi G, Koganty RR, Qiu D, Lloyd KO, Livingston PO (1998) A novel and efficient method for synthetic carbohydrate conjugation vaccine prepapation: synthesis of sialyl Tn-KLH conjugate using a 4-(4-N-maleimidomethyl)-cyclohexane-1-carboxyl hydrazide (MMCCH) linker arm. Glycoconj J 15:217–221
Rotz LD, Khan AS, Lillibridge SR, Ostroff SM, Hughes JM (2002) Public health assessment of potential biological terrorism agents. Emerg Infect Dis 8:225–230
Saksena R, Adamo R, Kováč P (2005) Studies toward a conjugate vaccine for anthrax. Synthesis and characterization of anthrose [4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-d-glucopyranose] and its methyl glycosides. Carbohydr Res 340:1591–1600
Saksena R, Adamo R, Kováč P (2006) Synthesis of the tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium. Bioorg Med Chem Lett 16:615–617
Saksena R, Adamo R, Kováč P (2007) Immunogens related to the synthetic tetrasaccharide side chain of the Bacillus anthracis exosporium. Bioorg Med Chem 15:4283–4310
Sarkar K, Mukherjee I, Roy N (2003) Synthesis of the trisaccharide repeating unit of the O-antigen related to the enterohemorrhagic Escherichia coli type O26:H. J Carbohydr Chem 22:95–107
Seeberger PH, Werz DB (2007) Synthesis and medical application of oligosaccharides. Nature 446:1046–1051
Sterne M (1939) The use of anthrax vaccines prepared from avirulent (uncapsulated) variants of Bacillus anthracis. J Vet Sci Anim Ind 13:307–312
Sylvestre P, Couture-Tosi E, Mock M (2002) A collagen-like surface glycoprotein is a structural component of the Bacillus anthracis exosporium. Mol Microbiol 45:169–178
Tamborrini M, Werz DB, Frey J, Pluschke G, Seeberger PH (2006) Anti-carbohydrate antibodies for detection of anthrax spores. Angew Chem Int Ed 45:6581–6582
Tamborrini M, Oberli MA, Werz DB, Schürch N, Frey J, Seeberger PH, Pluschke G (2009) Immuno-detection of anthrose containing tetrasaccharide in the exosporium of Bacillus anthracis and Bacillus cereus strains. JAMA 106:1618–1628
Tigertt WD (1980) William Smith Greenfield, M.D., F.R.C.P, Professor Superintendent, the Brown Animal Sanatory Institution (1878–81) Concerning the priority due to him for the production of the first vaccine against anthrax. J Hyg London:415–420
Vasan M, Rauvolfova J, Wolfert MA, Leoff C, Kannenberg EL, Quinn CP, Carlson RW, Boons GJ (2008) Chemical synthesis and immunological properties of oligosaccharides derived from the vegetative cell wall of Bacillus anthracis. Chembiochem 9:1716–1720
Wang ZG, Williams LJ, Zhang XF, Zatorski A, Kudryashov V, Ragupathi G, Spassova M, Bornmann W, Slovin SF, Scher HI, Livingston PO, Lloyd KO, Danishefsky SJ (2000) Polyclonal antibodies from patients immunized with a globo H-keyhole limpet hemocyanin vaccine: isolation, quantification, and characterization of immune responses by using totally synthetic immobilized tumor antigens. Proc Natl Acad Sci USA 97:2719–2724
Werz DB, Seeberger PH (2005) Total synthesis of antigen Bacillus anthracis tetrasaccharide-creation of an anthrax vaccine candidate. Angew Chem Int Ed 44:6315–6318
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer-Verlag/Wien
About this chapter
Cite this chapter
Oberli, M.A., Horlacher, T., Werz, D.B., Seeberger, P.H. (2012). Synthetic Oligosaccharide Bacterial Antigens to Produce Monoclonal Antibodies for Diagnosis and Treatment of Disease Using Bacillus anthracis as a Case Study. In: Kosma, P., Müller-Loennies, S. (eds) Anticarbohydrate Antibodies. Springer, Vienna. https://doi.org/10.1007/978-3-7091-0870-3_2
Download citation
DOI: https://doi.org/10.1007/978-3-7091-0870-3_2
Published:
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-0869-7
Online ISBN: 978-3-7091-0870-3
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)