Rigid conformation of tricyclic orthoesters of sugars

Bochkov, A. F.; Dashunin, V. M.; Kessenikh, A. V.; Kochetkov, N. K.; Naumov, A. D.; Obruchnikov, I. V.

doi:10.1016/s0008-6215(00)81193-3

Cited by 12 publications

(2 citation statements)

References 2 publications

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“…Then TCA 35 was coupled with glucose acceptor 13 in the presence of TMSOTf in an attempt to form a trisaccharide. However, acceptor 13 did not react while disaccharide 35 underwent rearrangement into tricyclic orthoester 36 , which was unexpectedly stable 58 , 59 . The “all- cis ” conformation of this intriguing compound was confirmed by single-crystal X-ray diffraction (CCDC 1520384, Supplementary Tables 2 , 3 , 4 , and 5 ).…”

Section: Resultsmentioning

confidence: 99%

Deciphering minimal antigenic epitopes associated with Burkholderia pseudomallei and Burkholderia mallei lipopolysaccharide O-antigens

et al. 2017

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Burkholderia pseudomallei (Bp) and Burkholderia mallei (Bm), the etiologic agents of melioidosis and glanders, respectively, cause severe disease in both humans and animals. Studies have highlighted the importance of Bp and Bm lipopolysaccharides (LPS) as vaccine candidates. Here we describe the synthesis of seven oligosaccharides as the minimal structures featuring all of the reported acetylation/methylation patterns associated with Bp and Bm LPS O-antigens (OAgs). Our approach is based on the conversion of an l-rhamnose into a 6-deoxy-l-talose residue at a late stage of the synthetic sequence. Using biochemical and biophysical methods, we demonstrate the binding of several Bp and Bm LPS-specific monoclonal antibodies with terminal OAg residues. Mice immunized with terminal disaccharide–CRM197 constructs produced high-titer antibody responses that crossreacted with Bm-like OAgs. Collectively, these studies serve as foundation for the development of novel therapeutics, diagnostics, and vaccine candidates to combat diseases caused by Bp and Bm.

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Section: Resultsmentioning

confidence: 99%

Deciphering minimal antigenic epitopes associated with Burkholderia pseudomallei and Burkholderia mallei lipopolysaccharide O-antigens

et al. 2017

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“…1 Not only these rigid structures were used for conformational studies of pyranoses, 2,3 but also proved to be of utility for the synthesis of the carbohydrate moiety present in bleomycin group antibiotics 4 and for the preparation of novel materials as well. In this regards, Nakatsubo reported the first synthesis of modified cellulose by cationic ring-opening polymerization of 3,6-di-O-benzyl-α-D-glucopyranose 1,2,4-orthopivalate, 5 with high stereoselectivity for the formation of (1→4)-β-glucosidic linkages and in high yield; 6 therefore derivatives of α-D-glucopyranose 1,2,4-orthoesters can be considered valuable building blocks for the design of advanced materials from cellulose.…”

Section: Introductionmentioning

confidence: 99%

Rapid occurrence of sugar tricyclic orthoesters by acid catalyzed intramolecular orthotransesterification

Moradei¹,

Mortier²,

Cirelli³

2005

Arkivoc

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Correlations between molecular parameters and the spin–spin coupling constants of vicinal protons: Criticism of the karplus equations

Воронцова

Bochkov

1974

Org. Magn. Reson.

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Abstract-Conformationally rigid systems such as xylopyranose J ,2,4-ortho esters (la) and (lb) and 10-methoxy-6-aza-isoadamantane (2), for which the identity of conformations both in the crystalline state and in solution can reasonably be assumed, provide good models for the study of experimental correlations between the spin-spin coupling constants ( J ) of the vicinal protons and the dihedral bond angles (DBA) determined from an X-ray study in the H-C-C-H bond system. The Karplus equations and their modifications (with and without corrections for the electronegativity of adjacent groups) were found to be unable to provide satisfactory correlations between these parameters.

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Rigid conformation of tricyclic orthoesters of sugars

Cited by 12 publications

References 2 publications

Deciphering minimal antigenic epitopes associated with Burkholderia pseudomallei and Burkholderia mallei lipopolysaccharide O-antigens

Deciphering minimal antigenic epitopes associated with Burkholderia pseudomallei and Burkholderia mallei lipopolysaccharide O-antigens

Rapid occurrence of sugar tricyclic orthoesters by acid catalyzed intramolecular orthotransesterification

Correlations between molecular parameters and the spin–spin coupling constants of vicinal protons: Criticism of the karplus equations

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