617-04-9Relevant articles and documents
Solid-state NMR spectroscopic analysis of the Ca2+-dependent mannose binding of pradimicinA
Nakagawa, Yu,Masuda, Yuichi,Yamada, Keita,Doi, Takashi,Takegoshi,Igarashi, Yasuhiro,Ito, Yukishige
, p. 6084 - 6088 (2011)
Aggregation facilitates analysis: The Ca2+-dependent mannose (Man) binding of the nonpeptidic carbohydrate binder pradimicinA (PRM-A) was investigated in the solid state. The use of PRM-A aggregates eliminated problems associated with the three-component equilibrium. A combination of 113CdNMR spectroscopy and 2D dipolar-assisted rotational resonance revealed the mannose-binding site of PRM-A and the crucial role of the Ca 2+ ion (see binding model). Copyright
Quadoctomycin, a 48-membered macrolide antibiotic from Streptomyces sp. MM168-141F8
Sawa, Ryuichi,Kubota, Yumiko,Umekita, Maya,Hatano, Masaki,Hayashi, Chigusa,Igarashi, Masayuki
, p. 91 - 96 (2018)
Drug-resistant bacteria are still emerging, and screening of new skeletal antibiotics is important. During our continuous screening for antimicrobial agents, we discovered a new antimicrobial, named quadoctomycin, from solid culture of Streptomyces sp. MM168-141F8. The substance was purified by solvent extraction, silica gel chromatography and HPLC. Structural elucidation of quadoctomycin was performed by MS and NMR analyses and chemical degradation. Quadoctomycin possesses a 48-membered polyol macrolide skeleton in which an α-D-mannoside is connected to C-22 by an O-glycosidic linkage. The structure of quadoctomycin was found to be related to that of monazomycin A based on the analyses of NMR spectra in the same solvent (pyridine-d 5). Quadoctomycin showed potent antibacterial activity against Staphylococcus aureus, including methicillin-resistant S. aureus, and other Gram-positive pathogenic bacteria such as Enterococcus faecalis and E. faecium (including drug-resistant strains), but did not show activity toward Gram-negative bacteria or Candida albicans.
Acetyl Group Migration across the Saccharide Units in Oligomannoside Model Compound
Lassfolk, Robert,Rahkila, Jani,Johansson, Mikael P.,Ekholm, Filip S.,W?rn?, Johan,Leino, Reko
, p. 1646 - 1654 (2019)
Acetylated oligosaccharides are common in nature. While they are involved in several biochemical and biological processes, the role of the acetyl groups and the complexity of their migration has largely gone unnoticed. In this work, by combination of organic synthesis, NMR spectroscopy and quantum chemical modeling, we show that acetyl group migration is a much more complex phenomenon than previously known. By use of synthetic oligomannoside model compounds, we demonstrate, for the first time, that the migration of acetyl groups in oligosaccharides and polysaccharides may not be limited to transfer within a single monosaccharide moiety, but may also involve migration over a glycosidic bond between two different saccharide units. The observed phenomenon is not only interesting from the chemical point of view, but it also raises new questions about the potential biological role of acylated carbohydrates in nature.
Synthesis of branched-phosphodiester and mannose-centered fucosylated glycoclusters and their binding studies with Burkholderia ambifaria lectin (BambL)
Ligeour, Caroline,Audfray, Aymeric,Gillon, Emilie,Meyer, Albert,Galanos, Nicolas,Vidal, Sebastien,Vasseur, Jean-Jacques,Imberty, Anne,Morvan, Francois
, p. 19515 - 19524 (2013)
Five fucosylated glycoclusters exhibiting 4, 6 or 8 residues were synthesised with two different spatial environments based on mannose-centered and branched-phosphodiester scaffolds. Their synthesis was performed in solution using phosphoramidite chemistry to generate phosphodiester linkages, combined with Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC). The multivalent ligands were evaluated for their ability to bind to Burkholderia ambifaria Lectin (BambL). Binding evaluation was performed through inhibition of hemagglutination (HIA), surface plasmon resonance (SPR) and isothermal titration microcalorimetry (ITC). All fucosylated glycoclusters exhibited a higher affinity to BambL than methyl α-l-fucoside. A dissociation constant of 43 nM was observed for the fucocluster exhibiting four residues with the branched-phosphodiester spatial environment corresponding to a 22-fold increase in comparison with methyl α-l-fucoside. These multivalent fucoclusters represent the first example of ligands of high affinity to BambL.
General Strategy for the Synthesis of Rare Sugars via Ru(II)-Catalyzed and Boron-Mediated Selective Epimerization of 1,2- trans-Diols to 1,2- cis-Diols
Li, Xiaolei,Tang, Weiping,Wu, Jicheng
supporting information, p. 3727 - 3736 (2022/03/02)
Human glycans are primarily composed of nine common sugar building blocks. On the other hand, several hundred monosaccharides have been discovered in bacteria and most of them are not readily available. The ability to access these rare sugars and the corresponding glycoconjugates can facilitate the studies of various fundamentally important biological processes in bacteria, including interactions between microbiota and the human host. Many rare sugars also exist in a variety of natural products and pharmaceutical reagents with significant biological activities. Although several methods have been developed for the synthesis of rare monosaccharides, most of them involve lengthy steps. Herein, we report an efficient and general strategy that can provide access to rare sugars from commercially available common monosaccharides via a one-step Ru(II)-catalyzed and boron-mediated selective epimerization of 1,2-trans-diols to 1,2-cis-diols. The formation of boronate esters drives the equilibrium toward 1,2-cis-diol products, which can be immediately used for further selective functionalization and glycosylation. The utility of this strategy was demonstrated by the efficient construction of glycoside skeletons in natural products or bioactive compounds.
Carbon glycoside glycosylated tetravalent platinum compound as well as synthesis method and application thereof
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Paragraph 0064-0067, (2021/07/08)
The invention provides a carbon glycoside glycosylated tetravalent platinum compound, a synthesis method and application thereof. R1 and R2 are independently C1-C4 lower alkanes, R3 is glucose, galactose, mannose and ribose, different sugars are used as raw materials, and a series of carbon glycoside glycosylated tetravalent platinum compounds are synthesized through protection and deprotection reaction and metallization reaction of the sugars. The synthesis method is simple, the used raw materials are cheap and easy to obtain, the glycosylated tetravalent platinum compound has the capacity of targeting glucose transporter protein and has potential application value in the field of cancer treatment, introduction of a C-glucosidic bond enables the series of compounds to have the capacity of resisting hydrolysis of beta-glucosidase, and the compound is expected to be applied to the field of oral antitumor drugs.
