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Pyranose

About: Pyranose is a research topic. Over the lifetime, 1619 publications have been published within this topic receiving 35348 citations. The topic is also known as: pyranoses & hexopyranose.


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Journal ArticleDOI
TL;DR: A series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1-C2 fragmentation reaction under reductive conditions.
Abstract: A series of anomeric nitrate esters and N-phthalimido glycosides of carbohydrates in furanose and pyranose forms have been synthesized in order to generate the corresponding alkoxy radicals and study the C1−C2 fragmentation reaction under reductive conditions. This reaction constitutes a two-step method for the transformation of carbohydrates into the corresponding alditols with one less carbon. Using this methodology, interesting four- and five-carbon building blocks for natural products synthesis possessing d-erythritol, d-threitol, d-xylitol, and d-arabinitol stereochemistry have been prepared. The synthesis of 1,2-O-isopropylidene-β-l-threose (40) and 1-acetamido-2,4,5-tri-O-acetyl-d-arabinitol (50) have also been achieved from 1,2:5,6-di-O-isopropylidene-β-d-glucofuranose and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-d-glucopyranose, respectively.

21 citations

Journal ArticleDOI
TL;DR: A new methodology to synthesize exo-glycals bearing both a sulfone and a phosphonate and was applied to eight different carbohydrates from the furanose and pyranose series, finding that the Z/E configurations of these tetrasubstituted enol ethers could be ascertained using NMR spectroscopic techniques.
Abstract: This study reports a new methodology to synthesize exo-glycals bearing both a sulfone and a phosphonate. This synthetic strategy provides a way to generate exo-glycals displaying two electron-withdrawing groups and was applied to eight different carbohydrates from the furanose and pyranose series. The Z/E configurations of these tetrasubstituted enol ethers could be ascertained using NMR spectroscopic techniques. Deprotection of an exo-glycal followed by an UMP (uridine monophosphate) coupling generated two new UDP (uridine diphosphate)-galactofuranose analogues. These two Z/E isomers were evaluated as inhibitors of UGM, GlfT1, and GlfT2, the three mycobacterial galactofuranose processing enzymes. Molecule 46-(E) is the first characterized inhibitor of GlfT1 reported to date and was also found to efficiently inhibit UGM in a reversible manner. Interestingly, GlfT2 showed a better affinity for the (Z) isomer. The three enzymes studied in the present work are not only interesting because, mechanistically, they are still the topic of intense investigations, but also because they constitute very important targets for the development of novel antimycobacterial agents.

21 citations

Journal ArticleDOI
TL;DR: In this article, two crystalline forms of the sugar having different signs of optical rotation were obtained and the absence of an SH absorption in their infrared spectra indicates the dextrorotatory and laevorotatory forms to be the α- D -pyranose and β- D-pyransose isomers, respectively.

21 citations

Journal ArticleDOI
TL;DR: A Norrish type II photoelimination to give an isolable acyclic photoenol intermediate II is followed by an intramolecular enolexo aldolization that leads to a new type of cyclopentitol derivative III.
Abstract: Opened and closed: Visible-light photostimulation of 2,3-diuloses I triggers an unprecedented sequential rearrangement: A Norrish type II photoelimination to give an isolable acyclic photoenol intermediate II is followed by an intramolecular enolexo aldolization. The contraction of the pyranose ring in this process leads to a new type of cyclopentitol derivative III. R=acyl, alkyl, silyl group.

21 citations

Journal ArticleDOI
TL;DR: The first crystal structure data on an Amadori compound, N-(1-deoxy-beta-D-fructopyranos-1-yl)-glycine, are reported, which forms a three-dimensional network of two infinite chains that have an ammonium group as a common segment.

21 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202317
202228
202118
202027
201926
201819