Synthesis of phosphate derivatives related to the glycosidase inhibitor salacinol

Bhat, Ramakrishna G.; Kumar, Nag S.; Pinto, B. Mario

doi:10.1016/j.carres.2007.05.030

Cited by 9 publications

(6 citation statements)

References 36 publications

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“…With carboxylate inner salt as human maltase glucoamylase inhibitor TOF (DHB) Salacinol analogues Phosphate analogues as glycosidase inhibitors (Bhat, et al, 2007) (Nasi, et al, 2007) (Prante, et al, 2007) 1H-(1,2,3-triazol-1-yl)-mannosides As selective galectin-3 and 9N inhibitors TOF (Tejler, et al, 2007) 1 Format (not all items present): MALDI method (matrix), derivative. ''MALDI'' is used when the instrument is not specified.…”

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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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

View full text Add to dashboard Cite

show abstract

“…30). 123 The de-Osulfonated derivatives (109,110) derived from biologically active C-5 0 diastereomers of kotalanol, (107) and (108), were found to be more active against ntMGAM than the parent compounds, supporting the general proposition that de-O-sulfonation leads to an increase in the inhibitory activity against ntMGAM compared to the parent sulfated compounds. 22 To study the effect of heteroatom substitution on the inhibitory activities of kotalanol (6) and de-O-sulfonated kotalanol (10), Mohan et al 122 designed their nitrogen (111)(112) and selenium analogues (114-115, Fig.…”

Section: Fig 13mentioning

confidence: 87%

“…22) were prepared, in which the sulfate moiety on the acyclic side chain has been substituted with a phosphate moiety and aer screening, it was found to not effective against MGAM. 110 New salacinol analogues (72-79, Fig. 23) based on novel anhydroseleno-and anhydrothio-allitols, derived from Dgulono-g-lactone and L-ascorbic acid, have also been synthesized.…”

Section: Fig 13mentioning

confidence: 99%

“…78,124 These outcomes undoubtedly signify the importance of the ve-membered ring thiocyclitol moiety with a permanent positive charge and thus provide further support for transition state mimicry by these sulfonium-ion glucosidase inhibitors. The inhibitory activities of all synthesized kotalanol analogues (105)(106)(107)(108)(109)(110)(111)(112)(113)(114)(115)(116)(117)(118) against the maltase activity of recombinant, ntMGAM are summarized in Table 6.…”

Section: Fig 13mentioning

confidence: 99%

“…Diastereomers of kotalanol(105,107,108) and de-Osulfonated kotalanol(106,109,110) and their inhibitory activity against ntMGAM.…”

mentioning

confidence: 99%

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