Seven-membered ring boronates at trans-diol moieties of carbohydrates

Meiland, Marcel; Heinze, Thomas; Guenther, Wolfgang; Liebert, Tim

doi:10.1016/j.tetlet.2008.11.043

Cited by 25 publications

(20 citation statements)

References 11 publications

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“…In addition, 1,2-diols have a range of shapes and conformations: cis and trans diols have different reactivity with the same boronic acid [50], as do cis-1,2-diols on five-versus six-membered rings [28]. Aromaticity and ring strain are also contributing factors, with catechols reacting differently to cyclic aliphatic diols [71].…”

Section: Introductionmentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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Small molecules have long been used for the selective recognition of a wide range of analytes. The ability of these chemical receptors to recognise and bind to specific targets mimics certain biological processes (such as proteinsubstrate interactions) and has therefore attracted recent interest. Due to the abundance of biological molecules possessing polyhydroxy motifs, boronic acids-which form fivemembered boronate esters with diols-have become increasingly popular in the synthesis of small chemical receptors. Their targets include biological materials and natural products including phosphatidylinositol bisphosphate, saccharides and polysaccharides, nucleic acids, metal ions and the neurotransmitter dopamine. This review will focus on the many ways in which small chemical receptors based on boronic acids have been used as biochemical tools for various purposes, including sensing and detection of analytes, interference in signalling pathways, enzyme inhibition and cell delivery systems. The most recent developments in each area will be highlighted.

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Section: Introductionmentioning

confidence: 99%

Molecular recognition with boronic acids—applications in chemical biology

2013

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“…6,11 After introduction into the mass spectrometer, the spectra were measured using electron impact (EI) ionization. All samples with molar ratio Me-b-D-clb:TPB higher than 1:1 showed fragment ions at m/z 250, which is a hint for the existence of a seven-membered diboronate ring at trans-1,2-diol moieties at C-2 and C-3.…”

Section: Ms Studiesmentioning

confidence: 99%

“…6,12 Thus, the esterification of Me-b-D-clb with PBA was carried out in aprotic solvents by azeotropic removal of water using a molar ratio 1:1.1. In the 1 H NMR spectrum of the phenylboronate sample 2 (Scheme 2) five instead of seven signals for unmodified OH moieties between 5.5 and 4.0 ppm were found.…”

Section: Synthesis Of Phenylboronates and Nmr Analysesmentioning

confidence: 99%

“…Therefore this study attempted to understand the conversion of boronic acids with glucopyranose-based compounds, specifically the reaction of phenylboronic acid (PBA) with methyl-a-D-glucopyranoside (Me-a-D-Glcp). 6 Fast formation of a six-membered ring through C-4 and C-6 and the existence of a seven-membered diboronate ring at the trans-1,2-diol moieties of C-2 and C-3 was proven by means of NMR and MS, and 'coordination-induced shifts' (CIS) for 13 C NMR spectra were revealed. This new tool could now be exploited to investigate the more complex structures which may be formed in the case of the boronation of glucopyranose-based oligomers, especially cellodextrins.…”

Section: Introductionmentioning

confidence: 99%

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Studies on the boronation of methyl-β-d-cellobioside—a cellulose model

Meiland

Heinze

Guenther

et al. 2010

Carbohydrate Research

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“…Mimics for cellulose are very useful for the investigation of the hydrogen bond network using solid-state techniques (Rencurosi et al 2002) or for studies of the interaction with boric or boronic acid-type compounds (Meiland et al 2009(Meiland et al , 2010. Moreover, the model compounds are appropriate to investigate the induced conformational changes in cellulose structure upon complexation with metal ions during the dissolution in aqueous solutions that are commonly applied in DP measurements (Saalwaechter et al 2000;Klemm et al 1998).…”

Section: Introductionmentioning

confidence: 99%

Alkyl β-d-cellulosides: non-reducing cellulose mimics

et al. 2011

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Non-reducing cellulose mimics, termed alkyl b-D-cellulosides, were successfully prepared by two efficient multi-step syntheses starting from commercially available microcrystalline cellulose or cellulose triacetate. Introduction of the alkoxy moiety and degradation of the cellulose backbone was carried out in the presence of a Lewis acid, on one hand. On the other hand, cellulose hydrolysis mediated by mineral acids was combined with b-glycosidation performed in the presence of silver salts. The samples obtained possess a number-average degree of polymerization from 5 to 25, determined by sizeexclusion chromatography, elemental analyses, NMR spectroscopy, and MALDI-TOF mass spectrometry. Samples in multi-gram quantities were available. Selective formation of a b-glycosidic bond between the C-1 atom of the reducing end group and alkoxy moieties was confirmed by a combination of 2D NMR spectroscopic and MALDI-TOF MS techniques. Due to the blocking of the aldehyde function, the cellulosides described are very useful mimics for the investigation of polysaccharide interactions with other complex molecules such as proteins or to determine polymer properties in solution or in solid state.

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Seven-membered ring boronates at trans-diol moieties of carbohydrates

Cited by 25 publications

References 11 publications

Molecular recognition with boronic acids—applications in chemical biology

Molecular recognition with boronic acids—applications in chemical biology

Studies on the boronation of methyl-β-d-cellobioside—a cellulose model

Alkyl β-d-cellulosides: non-reducing cellulose mimics

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