Show legend Show as text

Structure type: polymer chemical repeating unit ; n=3-4
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86

• Article ID: 3469
  Forsberg LS, Carlson RW "Structural characterization of the primary O-antigenic polysaccharide of the Rhizobium leguminosarum 3841 lipopolysaccharide and identification of a new 3-acetimidoylamino-3-deoxyhexuronic acid glycosyl component: a unique O-methylated glycan of uniform size, containing 6-deoxy-3-O-methyl-D-talose, n-acetylquinovosamine, and rhizoaminuronic acid (3-acetimidoylamino-3-deoxy-D-gluco-hexuronic acid)" - Journal of Biological Chemistry 283(23) (2008) 16037-16050
  

  Rhizobium are Gram-negative bacteria that survive intracellularly, within host membrane-derived plant cell compartments called symbiosomes. Within the symbiosomes the bacteria differentiate to bacteroids, the active form that carries out nitrogen fixation. The progression from free-living bacteria to bacteroid is characterized by physiological and morphological changes at the bacterial surface, a phase shift with an altered array of cell surface glycoconjugates. Lipopolysaccharides undergo structural changes upon differentiation from the free living to the bacteroid (intracellular) form. The array of carbohydrate structures carried on lipopolysaccharides confer resistance to plant defense mechanisms and may serve as signals that trigger the plant to allow the infection to proceed. We have determined the structure of the major O-polysaccharide (OPS) isolated from free living Rhizobium leguminosarum 3841, a symbiont of Pisum sativum, using chemical methods, mass spectrometry, and NMR spectroscopy analysis. The OPS is composed of several unusual glycosyl residues, including 6-deoxy-3-O-methyl-d-talose and 2-acetamido-2deoxy-l-quinovosamine. In addition, a new glycosyl residue, 3-acetimidoylamino-3-deoxy-d-gluco-hexuronic acid was identified and characterized, a novel hexosaminuronic acid that does not have an amino group at the 2-position. The OPS is composed of three to four tetrasaccharide repeating units of →4)-β-dGlcp3NAmA-(1→4)-[2-O-Ac-3-O-Me-α-D-6dTalp-(1→3)]-α-l-Fucp-(1→3)-α-L-QuipNAc-(1→. The unique 3-amino hexuronate residue, rhizoaminuronic acid, is an attractive candidate for selective inhibition of OPS synthesis

  O-antigenic polysaccharide, Rhizobium leguminosarum, nitrogen fixation

  NCBI PubMed ID: 18387959
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia 30605, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, acid hydrolysis, MALDI-TOF MS, composition analysis, alkaline hydrolysis, ESI-QTOF-MS
  
   
  
  Rhizobium leguminosarum 3841
  CSDB ID 22644 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_142489,IEDB_144562,IEDB_152214,SB_86

• Article ID: 3469
  Forsberg LS, Carlson RW "Structural characterization of the primary O-antigenic polysaccharide of the Rhizobium leguminosarum 3841 lipopolysaccharide and identification of a new 3-acetimidoylamino-3-deoxyhexuronic acid glycosyl component: a unique O-methylated glycan of uniform size, containing 6-deoxy-3-O-methyl-D-talose, n-acetylquinovosamine, and rhizoaminuronic acid (3-acetimidoylamino-3-deoxy-D-gluco-hexuronic acid)" - Journal of Biological Chemistry 283(23) (2008) 16037-16050
  

  Rhizobium are Gram-negative bacteria that survive intracellularly, within host membrane-derived plant cell compartments called symbiosomes. Within the symbiosomes the bacteria differentiate to bacteroids, the active form that carries out nitrogen fixation. The progression from free-living bacteria to bacteroid is characterized by physiological and morphological changes at the bacterial surface, a phase shift with an altered array of cell surface glycoconjugates. Lipopolysaccharides undergo structural changes upon differentiation from the free living to the bacteroid (intracellular) form. The array of carbohydrate structures carried on lipopolysaccharides confer resistance to plant defense mechanisms and may serve as signals that trigger the plant to allow the infection to proceed. We have determined the structure of the major O-polysaccharide (OPS) isolated from free living Rhizobium leguminosarum 3841, a symbiont of Pisum sativum, using chemical methods, mass spectrometry, and NMR spectroscopy analysis. The OPS is composed of several unusual glycosyl residues, including 6-deoxy-3-O-methyl-d-talose and 2-acetamido-2deoxy-l-quinovosamine. In addition, a new glycosyl residue, 3-acetimidoylamino-3-deoxy-d-gluco-hexuronic acid was identified and characterized, a novel hexosaminuronic acid that does not have an amino group at the 2-position. The OPS is composed of three to four tetrasaccharide repeating units of →4)-β-dGlcp3NAmA-(1→4)-[2-O-Ac-3-O-Me-α-D-6dTalp-(1→3)]-α-l-Fucp-(1→3)-α-L-QuipNAc-(1→. The unique 3-amino hexuronate residue, rhizoaminuronic acid, is an attractive candidate for selective inhibition of OPS synthesis

  O-antigenic polysaccharide, Rhizobium leguminosarum, nitrogen fixation

  NCBI PubMed ID: 18387959
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia 30605, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, acid hydrolysis, MALDI-TOF MS, composition analysis, alkaline hydrolysis, ESI-QTOF-MS
  
   
  
  Rhizobium leguminosarum 3841
  CSDB ID 22943 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_142489,IEDB_144562,IEDB_152214,SB_86

• Article ID: 3469
  Forsberg LS, Carlson RW "Structural characterization of the primary O-antigenic polysaccharide of the Rhizobium leguminosarum 3841 lipopolysaccharide and identification of a new 3-acetimidoylamino-3-deoxyhexuronic acid glycosyl component: a unique O-methylated glycan of uniform size, containing 6-deoxy-3-O-methyl-D-talose, n-acetylquinovosamine, and rhizoaminuronic acid (3-acetimidoylamino-3-deoxy-D-gluco-hexuronic acid)" - Journal of Biological Chemistry 283(23) (2008) 16037-16050
  

  Rhizobium are Gram-negative bacteria that survive intracellularly, within host membrane-derived plant cell compartments called symbiosomes. Within the symbiosomes the bacteria differentiate to bacteroids, the active form that carries out nitrogen fixation. The progression from free-living bacteria to bacteroid is characterized by physiological and morphological changes at the bacterial surface, a phase shift with an altered array of cell surface glycoconjugates. Lipopolysaccharides undergo structural changes upon differentiation from the free living to the bacteroid (intracellular) form. The array of carbohydrate structures carried on lipopolysaccharides confer resistance to plant defense mechanisms and may serve as signals that trigger the plant to allow the infection to proceed. We have determined the structure of the major O-polysaccharide (OPS) isolated from free living Rhizobium leguminosarum 3841, a symbiont of Pisum sativum, using chemical methods, mass spectrometry, and NMR spectroscopy analysis. The OPS is composed of several unusual glycosyl residues, including 6-deoxy-3-O-methyl-d-talose and 2-acetamido-2deoxy-l-quinovosamine. In addition, a new glycosyl residue, 3-acetimidoylamino-3-deoxy-d-gluco-hexuronic acid was identified and characterized, a novel hexosaminuronic acid that does not have an amino group at the 2-position. The OPS is composed of three to four tetrasaccharide repeating units of →4)-β-dGlcp3NAmA-(1→4)-[2-O-Ac-3-O-Me-α-D-6dTalp-(1→3)]-α-l-Fucp-(1→3)-α-L-QuipNAc-(1→. The unique 3-amino hexuronate residue, rhizoaminuronic acid, is an attractive candidate for selective inhibition of OPS synthesis

  O-antigenic polysaccharide, Rhizobium leguminosarum, nitrogen fixation

  NCBI PubMed ID: 18387959
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia 30605, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, acid hydrolysis, MALDI-TOF MS, composition analysis, alkaline hydrolysis, ESI-QTOF-MS
  
   
  
  Rhizobium leguminosarum 3841
  CSDB ID 22944 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: de-O-acylated OPS
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86

• Article ID: 3469
  Forsberg LS, Carlson RW "Structural characterization of the primary O-antigenic polysaccharide of the Rhizobium leguminosarum 3841 lipopolysaccharide and identification of a new 3-acetimidoylamino-3-deoxyhexuronic acid glycosyl component: a unique O-methylated glycan of uniform size, containing 6-deoxy-3-O-methyl-D-talose, n-acetylquinovosamine, and rhizoaminuronic acid (3-acetimidoylamino-3-deoxy-D-gluco-hexuronic acid)" - Journal of Biological Chemistry 283(23) (2008) 16037-16050
  

  Rhizobium are Gram-negative bacteria that survive intracellularly, within host membrane-derived plant cell compartments called symbiosomes. Within the symbiosomes the bacteria differentiate to bacteroids, the active form that carries out nitrogen fixation. The progression from free-living bacteria to bacteroid is characterized by physiological and morphological changes at the bacterial surface, a phase shift with an altered array of cell surface glycoconjugates. Lipopolysaccharides undergo structural changes upon differentiation from the free living to the bacteroid (intracellular) form. The array of carbohydrate structures carried on lipopolysaccharides confer resistance to plant defense mechanisms and may serve as signals that trigger the plant to allow the infection to proceed. We have determined the structure of the major O-polysaccharide (OPS) isolated from free living Rhizobium leguminosarum 3841, a symbiont of Pisum sativum, using chemical methods, mass spectrometry, and NMR spectroscopy analysis. The OPS is composed of several unusual glycosyl residues, including 6-deoxy-3-O-methyl-d-talose and 2-acetamido-2deoxy-l-quinovosamine. In addition, a new glycosyl residue, 3-acetimidoylamino-3-deoxy-d-gluco-hexuronic acid was identified and characterized, a novel hexosaminuronic acid that does not have an amino group at the 2-position. The OPS is composed of three to four tetrasaccharide repeating units of →4)-β-dGlcp3NAmA-(1→4)-[2-O-Ac-3-O-Me-α-D-6dTalp-(1→3)]-α-l-Fucp-(1→3)-α-L-QuipNAc-(1→. The unique 3-amino hexuronate residue, rhizoaminuronic acid, is an attractive candidate for selective inhibition of OPS synthesis

  O-antigenic polysaccharide, Rhizobium leguminosarum, nitrogen fixation

  NCBI PubMed ID: 18387959
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia 30605, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, acid hydrolysis, MALDI-TOF MS, composition analysis, alkaline hydrolysis, ESI-QTOF-MS
  
   
  
  Rhizobium leguminosarum 3841
  CSDB ID 22945 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: (2->6)core-lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86

• Article ID: 3469
  Forsberg LS, Carlson RW "Structural characterization of the primary O-antigenic polysaccharide of the Rhizobium leguminosarum 3841 lipopolysaccharide and identification of a new 3-acetimidoylamino-3-deoxyhexuronic acid glycosyl component: a unique O-methylated glycan of uniform size, containing 6-deoxy-3-O-methyl-D-talose, n-acetylquinovosamine, and rhizoaminuronic acid (3-acetimidoylamino-3-deoxy-D-gluco-hexuronic acid)" - Journal of Biological Chemistry 283(23) (2008) 16037-16050
  

  Rhizobium are Gram-negative bacteria that survive intracellularly, within host membrane-derived plant cell compartments called symbiosomes. Within the symbiosomes the bacteria differentiate to bacteroids, the active form that carries out nitrogen fixation. The progression from free-living bacteria to bacteroid is characterized by physiological and morphological changes at the bacterial surface, a phase shift with an altered array of cell surface glycoconjugates. Lipopolysaccharides undergo structural changes upon differentiation from the free living to the bacteroid (intracellular) form. The array of carbohydrate structures carried on lipopolysaccharides confer resistance to plant defense mechanisms and may serve as signals that trigger the plant to allow the infection to proceed. We have determined the structure of the major O-polysaccharide (OPS) isolated from free living Rhizobium leguminosarum 3841, a symbiont of Pisum sativum, using chemical methods, mass spectrometry, and NMR spectroscopy analysis. The OPS is composed of several unusual glycosyl residues, including 6-deoxy-3-O-methyl-d-talose and 2-acetamido-2deoxy-l-quinovosamine. In addition, a new glycosyl residue, 3-acetimidoylamino-3-deoxy-d-gluco-hexuronic acid was identified and characterized, a novel hexosaminuronic acid that does not have an amino group at the 2-position. The OPS is composed of three to four tetrasaccharide repeating units of →4)-β-dGlcp3NAmA-(1→4)-[2-O-Ac-3-O-Me-α-D-6dTalp-(1→3)]-α-l-Fucp-(1→3)-α-L-QuipNAc-(1→. The unique 3-amino hexuronate residue, rhizoaminuronic acid, is an attractive candidate for selective inhibition of OPS synthesis

  O-antigenic polysaccharide, Rhizobium leguminosarum, nitrogen fixation

  NCBI PubMed ID: 18387959
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia 30605, USA
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, acid hydrolysis, MALDI-TOF MS, composition analysis, alkaline hydrolysis, ESI-QTOF-MS
  
   
  
  Rhizobium leguminosarum 3841
  CSDB ID 22946 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: ->4) Kdo of core-lipid A
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86

• Article ID: 3830
  Carlson RW, Forsberg LS, Kannenberg EL "Lipopolysaccharides in Rhizobium-Legume Symbioses" - Book: Endotoxins: Structure, Function and Recognition (series: Subcellular Biochemistry, 2010, Part 1) (2010) Vol. 53, Chapter 16, 339-386
  

  The establishment of nitrogen-fixing symbiosis between a legume plant and its rhizobial symbiont requires that the bacterium adapt to changing conditions that occur with the host plant that both promotes and allows infection of the host root nodule cell, regulates and resists the host defense response, permits the exchange of metabolites, and contributes to the overall health of the host. This adaptive process involves changes to the bacterial cell surface and, therefore, structural modifications to the lipopolysaccharide (LPS). In this chapter, we describe the structures of the LPSs from symbiont members of the Rhizobiales, the genetics and mechanism of their biosynthesis, the modifications that occur during symbiosis, and their possible functions.

  biosynthesis, lipopolysaccharides, structure, Rhizobium, symbiosis, plant defense

  NCBI PubMed ID: 20593275
  Publication DOI: 10.1007/978-90-481-9078-2_16
  Publisher: Springer Science+Business Media B.V.
  Correspondence: rcarlson@ccrc.uga.edu
  Editors: Wang X, Quinn PJ
  Institutions: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Rd., Athens, GA 30602, USA
  
   
  
  Rhizobium leguminosarum bv. viciae 3841
  CSDB ID 25564 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: (1->4) core-lipid A
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86

• Article ID: 4076
  Muszynski A, Laus M, Kijne JW, Carlson RW "Structures of the lipopolysaccharides from Rhizobium leguminosarum RBL5523 and its UDP-glucose dehydrogenase mutant (exo5)" - Glycobiology 21(1) (2011) 55-68
  

  Rhizobial lipopolysaccharide (LPS) is required to establish an effective symbiosis with its host plant. An exo5 mutant of R. leguminosarum RBL5523, strain RBL5808, is defective in UDP-glucose (Glc) dehydrogenase that converts UDP-Glc to UDP-glucuronic acid (GlcA). This mutant is unable to synthesize either UDP-GlcA or UDP-galacturonic acid (GalA) and is unable to synthesize extracellular and capsular polysaccharides, lacks GalA in its LPS, and is defective in symbiosis (Laus et. al. 2004. J. Bacteriol.186:6617-6625). Here, we determined and compared the structures of the RBL5523 parent and RBL5808 mutant LPSs. The parent LPS core oligosaccharide (OS), as with other R. leguminosarum and R. etli strains, is a Gal(1)Man(1)GalA(3)Kdo(3) octasaccharide in which each of the GalA residues is terminally linked. The core OS from the mutant lacks all three GalA residues. Also, the parent lipid A consists of a fatty acylated GlcNGlcNonate or GlcNGlcN disaccharide that has a GalA residue at the 4'-position, typical of other R. leguminosarum and R. etli lipids A. The mutant lipid A lacks the 4' GalA residue and the proximal glycosyl residue was only present as GlcNonate. In spite of these alterations to the lipid A and core OS, the mutant was still able to synthesize an LPS containing a normal O-chain polysaccharide (OPS), but at reduced levels. The structure of the OPS of the mutant LPS was identical to that of the parent and consists of an O-acetylated →4)-α-D-Glcp-(1→3)-α-D-QuipNAc-(1→ repeating unit.

  Lipopolysaccharide, structure, symbiosis, Rhizobium leguminosarum

  NCBI PubMed ID: 20817634
  Publication DOI: 10.1093/glycob/cwq131
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: rcarlson@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, University of Georgia, Athens, GA, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, HPAEC, DOC-PAGE, MALDI-TOF MS, de-O-acetylation, composition analysis, NMR-1D
  
   
  
  Rhizobium leguminosarum Rlv 3841
  CSDB ID 26895 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86

• Article ID: 4329
  Knirel YA "Structure of O-antigens" - Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
  

  The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.

  Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis

  Publication DOI: 10.1007/978-3-7091-0733-1_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Rhizobium leguminosarum bv. viciae 3841
  CSDB ID 27836 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137473

• Article ID: 4359
  Nazarenko EL, Crawford RJ, Ivanova EP "The structural diversity of carbohydrate antigens of selected Gram-negative marine bacteria" - Marine Drugs 9(10) (2011) 1914-1954
  

  Marine microorganisms have evolved for millions of years to survive in the environments characterized by one or more extreme physical or chemical parameters, e.g., high pressure, low temperature or high salinity. Marine bacteria have the ability to produce a range of biologically active molecules, such as antibiotics, toxins and antitoxins, antitumor and antimicrobial agents, and as a result, they have been a topic of research interest for many years. Among these biologically active molecules, the carbohydrate antigens, lipopolysaccharides (LPSs, O-antigens) found in cell walls of gram-negative marine bacteria, show great potential as candidates in the development of drugs to prevent septic shock due to their low virulence. The structural diversity of LPSs is thought to be a reflection of the ability for these bacteria to adapt to an array of habitats, protecting the cell from being compromised by exposure to harsh environmental stress factors. Over the last few years, the variety of structures of core oligosaccharides and O-specific polysaccharides from LPSs of marine microrganisms has been discovered. In this review, we discuss the most recently encountered structures that have been identified from bacteria belonging to the genera Aeromonas, Alteromonas, Idiomarina, Microbulbifer, Pseudoalteromonas, Plesiomonas and Shewanella of the Gammaproteobacteria phylum; Sulfitobacter and Loktanella of the Alphaproteobacteria phylum and to the genera Arenibacter, Cellulophaga, Chryseobacterium, Flavobacterium, Flexibacter of the Cytophaga-Flavobacterium-Bacteroides phylum. Particular attention is paid to the particular chemical features of the LPSs, such as the monosaccharide type, non-sugar substituents and phosphate groups, together with some of the typifying traits of LPSs obtained from marine bacteria. A possible correlation is then made between such features and the environmental adaptations undertaken by marine bacteria.

  O-specific polysaccharides, carbohydrate antigens, marine microorganisms

  NCBI PubMed ID: 22073003
  Publication DOI: 10.3390/md9101914
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: elnaz@piboc.dvo.ru
  Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok 690022, Russia, Faculty of Life and Social Sciences, Swinburne University of Technology, PO Box 218, Hawthorn, Victoria 3122, Australia
  Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, NMR-2D, FAB-MS, partial acid hydrolysis, NMR, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, acid hydrolysis, mild acid hydrolysis, HPAEC, ESI-ICR-MS, Smith degradation, chemical methods, MALDI-TOF MS, MS, de-O-acetylation, NMR-1D, GPC, alkaline hydrolysis, CE-ESI-MS, CE-MS, hydrazinolysis
  
   
  
  Shewanella japonica KMM 3601
  CSDB ID 28491 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-antigen
Contained glycoepitopes: IEDB_136045,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,SB_86

• Article ID: 6301
  Qin CJ, Ding MR, Tian GZ, Zou XP, Fu JJ, Hu J, Yin J "Chemical approaches towards installation of rare functional groups in bacterial surface glycans" - Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 20(6) (2022) 401-420
  

  Bacterial surface glycans perform a diverse and important set of biological roles, and have been widely used in the treatment of bacterial infectious diseases. The majority of bacterial surface glycans are decorated with diverse rare functional groups, including amido, acetamidino, carboxamido and pyruvate groups. These functional groups are thought to be important constituents for the biological activities of glycans. Chemical synthesis of glycans bearing these functional groups or their variants is essential for the investigation of structure-activity relationships by a medicinal chemistry approach. To date, a broad choice of synthetic methods is available for targeting the different rare functional groups in bacterial surface glycans. This article reviews the structures of naturally occurring rare functional groups in bacterial surface glycans, and the chemical methods used for installation of these groups.

  chemical synthesis, acetamidino group, amido group, bacterial surface glycan, carboxamido group, pyruvyl ketal

  NCBI PubMed ID: 35750381
  Publication DOI: 10.1016/S1875-5364(22)60177-8
  Journal NLM ID: 101504416
  Publisher: Beijing: Science Press; Elsevier
  Correspondence: J. Yin
  Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi, China, Wuxi School of Medicine, Jiangnan University, Wuxi, China
  
   
  
  Rhizobium leguminosarum 3841
  CSDB ID 9111 (all data & tools)