Application of Ball Milling Technology to Carbohydrate Reactions: I. Regioselective Primary Hydroxyl Protection of Hexosides and Nucleoside by Planetary Ball Milling‡

Patil, Premanand Ramrao; Kartha, K. P. Ravindranathan

doi:10.1080/07328300802218713

Cited by 32 publications

(14 citation statements)

References 34 publications

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“…It is important to highlight the regioselectivity in the amidation of 1b , since the amide was obtained on the acid group and the formation of the carbamate 9 was not observed. In this sense, Patil et al (2008) described the regioselective 6- O -tritylation/silylation (etherification) of methyl α - d -glucopyranoside or their derivatives under solvent-free conditions by planetary ball milling (dry grinding) [25]. Finally, the reaction of 3a and 3b with alkyl bromides (hexyl, octyl, and decyl chain lengths) was carried out in microwave and solvent-free conditions, as was described in a previous work [26].…”

Section: Resultsmentioning

confidence: 99%

N-alkylimidazolium Salts Functionalized with p-Coumaric and Cinnamic Acid: A Study of Their Antimicrobial and Antibiofilm Effects

et al. 2019

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The bacterial resistance to antibiotics has compromised the therapies used for bacterial infections. Nowadays, many strategies are being carried out to address this problem. Among them, the use of natural compounds like cinnamic and p-coumaric acids stands out. Nevertheless, their utilization is limited because of their unfavorable physicochemical properties. Due to the lack of new therapeutic alternatives for bacterial infections, novel strategies have emerged, such as the use of ionic liquids; given that they can show a broad spectrum of antibacterial activity, this is why we herein report the antibacterial and antibiofilm activity of a series of N-alkylimidazolium salts functionalized with p-coumaric and cinnamic acids. The results from this study showed better antibacterial activity against Gram-positive bacteria, with a predominance of the salts derived from coumaric acid and a correlation with the chain length. Additionally, a lower efficacy was observed in the inhibition of biofilm formation, highlighting the antibiofilm activity against Staphylococcus aureus, which decreased the production of the biofilm by 52% over the control. In conclusion, we suggest that the salts derived from p-coumaric acid are good alternatives as antibacterial compounds. Meanwhile, the salt derived from cinnamic acid could be a good alternative as an antibiofilm compound.

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Section: Resultsmentioning

confidence: 99%

N-alkylimidazolium Salts Functionalized with p-Coumaric and Cinnamic Acid: A Study of Their Antimicrobial and Antibiofilm Effects

et al. 2019

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“…''MALDI'' is used when the instrument is not specified. (Giri, et al, 2008) Aryl glycosides TOF/TOF Use of planetary ball mill to achieve solvent free synthesis (Patil & Kartha, 2008b) Biotin derivatives R-TOF (DHB) As multifunctional oligosaccharide tags (Chindarkar & Franz, 2008) Carbohydrate units (general) TOF (CHCA), ESI Preparation and use of p-alkoxyphenyl-type heavy fluorous tag (Mizuno., et al, 2008) Cello-and chitooligomers TOF Use of galactosyltransferase and α-lactalbumin to transfer galactose to glucose (Streicher, et al, 2008) 1,2-Cisglycosylation TOF (DHB), ESI Synthesis by naphthylmethyl ether mediated intramolecular aglycon delivery (Ishiwata, et al, 2008b) Derivatized hexosides R-TOF Regioselective 6-O-tritylation/silylation of various monosaccharides or their derivatives under solvent-free conditions by dry grinding (Patil & Kartha, 2008a) Disaccharides (1→6-linked) TOF Microwave-assisted stereospecific intra-molecular rearrangement catalyzed by Mo(VI) (Hricovíniová, 2008) Glc-β-(1→6)-Man-α-(1→6)-Glc-β-1→pentenyl trisaccharide MALDI "Cap-and-tag" strategy for solid phase oligosaccharide synthesis. Ac-capping and fluorous-tagging allowed separation of F-tagged oligosaccharide from Ac capped deletion sequences using fluorous extraction.…”

Section: R-tof (Dhb)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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“…A significant catalytic effect played by TBAB [59] has been evidenced in silylations, which might be ascribed once again to several mechanisms such as the generation of a more reactive silylating agent and/or a beneficial kinetic effect resulting from an increased ionic-strength in the reaction medium. These kinds of protections at primary positions can also be performed, with moderate to good yields, with a mechanochemical ball milling activation [60]. In addition, it has been demonstrated that total protection of saccharides through the solvent-free, non-mechanochemical installation of trimethylsilyl groups (TMS) is possible with hexamethyldisilazane activated by a catalytic amount of iodine [61].…”

Section: Selective Modifications Based On Formation Of Ether Linkagesmentioning

confidence: 99%

Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity

et al. 2020

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Owing to their abundance in biomass and availability at a low cost, carbohydrates are very useful precursors for products of interest in a broad range of scientific applications. For example, they can be either converted into basic chemicals or used as chiral precursors for the synthesis of potentially bioactive molecules, even including nonsaccharide targets; in addition, there is also a broad interest toward the potential of synthetic sugar-containing structures in the field of functional materials. Synthetic elaboration of carbohydrates, in both the selective modification of functional groups and the assembly of oligomeric structures, is not trivial and often entails experimentally demanding approaches practiced by specialized groups. Over the last years, a large number of solvent-free synthetic methods have appeared in the literature, often being endowed with several advantages such as greenness, experimental simplicity, and a larger scope than analogous reactions in solution. Most of these methods are catalytically promoted, and the catalyst often plays a key role in the selectivity associated with the process. This review aims to describe the significant recent contributions in the solvent-free synthetic chemistry of carbohydrates, devoting a special critical focus on both the mechanistic role of the catalysts employed and the differences evidenced so far with corresponding methods in solution.

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Application of Ball Milling Technology to Carbohydrate Reactions: I. Regioselective Primary Hydroxyl Protection of Hexosides and Nucleoside by Planetary Ball Milling‡

Cited by 32 publications

References 34 publications

N-alkylimidazolium Salts Functionalized with p-Coumaric and Cinnamic Acid: A Study of Their Antimicrobial and Antibiofilm Effects

N-alkylimidazolium Salts Functionalized with p-Coumaric and Cinnamic Acid: A Study of Their Antimicrobial and Antibiofilm Effects

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Solvent-Free Approaches in Carbohydrate Synthetic Chemistry: Role of Catalysis in Reactivity and Selectivity

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