Synthesis of pentasaccharide core structures corresponding to the genus-specific lipopolysaccharide epitope of Chlamydia

Kosma, Paul; Strobl, Martina; Allmaier, Günter; Schmid, E.; Brade, Helmut

doi:10.1016/0008-6215(94)84246-9

Cited by 22 publications

(13 citation statements)

References 26 publications

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“…Comparison to S25-23-The remarkable specificity of S25-23 toward the family-specific Kdo(238)Kdo(234)Kdo trisaccharide antigen led to it becoming the best characterized Chlamydiaceae family-specific antibody in the literature (18,20,23,31,35,61), but no crystals could be generated despite thousands of trials over the last 18 years. S25-23 and S25-26 have almost identical sequence with few mutations in the combining site (Table 6), and so S25-23 is likely to bind the antigen in a fashion similar to S25-26.…”

Section: Figure 2-continuedmentioning

confidence: 99%

Groove-type Recognition of Chlamydiaceae-specific Lipopolysaccharide Antigen by a Family of Antibodies Possessing an Unusual Variable Heavy Chain N-Linked Glycan

Haji-Ghassemi

Müller‐Loennies

Saldova

et al. 2014

Journal of Biological Chemistry

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Background: S25-26 displays remarkable specificity and avidity toward the unusual inner core LPS from Chlamydia. Results: Liganded and unliganded structures reveal bound antigen and significant ordered N-glycosylation on the variable heavy chain. Conclusion: Groove-type paratope recognizes the antigen in a manner distinct from all other Chlamydia-specific antibodies. Significance: Structural analysis of germ-line-coded antibodies provides insight to anaphylaxis induced by ␣-galactose (␣Gal) epitopes on therapeutic antibodies.

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Section: Figure 2-continuedmentioning

confidence: 99%

Groove-type Recognition of Chlamydiaceae-specific Lipopolysaccharide Antigen by a Family of Antibodies Possessing an Unusual Variable Heavy Chain N-Linked Glycan

Haji-Ghassemi

Müller‐Loennies

Saldova

et al. 2014

Journal of Biological Chemistry

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“…We first investigated the iodoalkoxylation of the glycal ester 15 with alcohols 13 (Scheme and Table 1). Treatment of the benzyl‐protected glycal ester 14 and primary alcohols 13 a with NIS and TfOH provided the 3‐iodo‐α‐glycoside α‐ 18 a in 93 % yield with excellent selectivity 11. Notably, although iodoalkoxylation of glycals in the synthesis of α‐linked 2‐deoxyglycosides is known to proceed under mildly oxidative conditions,12 the use of a stoichiometric amount of TfOH was critical for the iodoalkoxylation of glycal ester 14 to proceed.…”

Section: Methodsmentioning

confidence: 99%

“…Next, the glycosylation of KDO derivatives 13 c – e at the C8 position was examined. The methyl glycoside 13 c was converted to the corresponding α‐glycoside α‐ 18 c in 73 % yield with α/β=92:8 11. On the other hand, glycosyl sulfoxide 13 e was difficult to prepare because of its instability.…”

Section: Methodsmentioning

confidence: 99%

Stereoselective Synthesis of Oligo‐α(2,8)‐3‐deoxy‐D‐manno‐2‐octulosonic Acid Derivatives

Tanaka

Takahashi

2006

Angew Chem Int Ed

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Iodoalkoxylation (see scheme) of a glycal with an acyclic saccharide precursor leads to an efficient stereoselective synthesis of di‐ and tri‐α(2,8)‐3‐deoxy‐D‐manno‐2‐octulosonic acid (KDO; see picture). The glycal forms α‐linked 3‐iodo‐KDO derivatives. The opening of the pyran ring improves the reactivity of the C8 hydroxy group. NIS=N‐iodosuccimide, Tf=triflate, M.S.=molecular sieves

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“…Antibodies to chlamydia were searched for by an enzymelinked immunosorbent assay (ELISA) with recombinant chlamydial LPS as antigen (Kosma et al 1994) (IgG, IgM and IgA rELISA, MEDAC, Hamburg, Germany), and with a synthetic C. pneumoniae outer membrane (OM) peptide antigen (IgG, IgA ELISA, Labsystems, Helsinki, Finland). The commercially available tests were performed according to the manufacturers' instructions.…”

Section: Serologymentioning

confidence: 99%

Chlamydia pneumoniae in central retinal artery occlusion

Vécsei

Kircher

Reitner

et al. 2002

Acta Ophthalmologica Scandinavica

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ABSTRACT.Purpose: There is increasing evidence that the common respiratory human pathogen Chlamydia pneumoniae has a causative role in atherosclerosis. We investigated the association of this pathogen with acute central retinal artery occlusion (CRAO). Patients and Methods: Sera of 14 consecutive patients with CRAO and of 14 age-and sex-matched control subjects were examined. Antibodies against chlamydial lipopolysaccharide (LPS) and outer membrane proteins of C. pneumoniae were determined by an enzyme-linked immunosorbent assay (ELISA). Results: In the CRAO group, seven patients (50%) were found to be IgA positive, 12 (86%) were IgG positive and one (7%) was IgM positive for chlamydial LPS antibodies. In the control group 36%, 79% and 14% were IgA, IgG and IgM positive, respectively. The results showed no significant difference between the groups. In the CRAO group, IgA, IgG and IgM antibodies to C. pneumoniae were found in 43%, 79% and 0% of subjects, respectively. These findings did not differ significantly from those pertaining to matched controls. Conclusions: These data do not support an association between acute CRAO and current C. pneumoniae infection.

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Synthesis of pentasaccharide core structures corresponding to the genus-specific lipopolysaccharide epitope of Chlamydia

Cited by 22 publications

References 26 publications

Groove-type Recognition of Chlamydiaceae-specific Lipopolysaccharide Antigen by a Family of Antibodies Possessing an Unusual Variable Heavy Chain N-Linked Glycan

Groove-type Recognition of Chlamydiaceae-specific Lipopolysaccharide Antigen by a Family of Antibodies Possessing an Unusual Variable Heavy Chain N-Linked Glycan

Stereoselective Synthesis of Oligo‐α(2,8)‐3‐deoxy‐D‐manno‐2‐octulosonic Acid Derivatives

Chlamydia pneumoniae in central retinal artery occlusion

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