d-Penturonic acids: solution studies of stable-isotopically enriched compounds by 1H- and 13C-n.m.r. spectroscopy

Wu, Jian; Serianni, Anthony S.

doi:10.1016/0008-6215(91)80112-z

Cited by 31 publications

(29 citation statements)

References 23 publications

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“…The identification of 8a and 8b was made by comparison with 13 C NMR chemical shifts of known compounds. 13 This observation suggests that for reactions at lower concentrations, there may be pathways that are able to shift the equilibrium toward the thermodynamically less favored aldoses; in this specific case, the aldoses may be stabilized as a cyclic hemiacetal.…”

Section: Reaction Of Dhf With Glyoxylatementioning

confidence: 99%

Exploratory Experiments on the Chemistry of the “Glyoxylate Scenario”: Formation of Ketosugars from Dihydroxyfumarate

Sagi

Punna

et al. 2012

J. Am. Chem. Soc.

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In the context of a “glyoxylate scenario” of primordial metabolism,1 the reactions of dihydroxyfumarate (DHF) with reactive small molecule aldehydes (e.g., glyoxylate, formaldehyde, glycolaldehyde, and glyceraldehyde) in water were investigated and shown to form dihydroxyacetone, tetrulose, and the two pentuloses, with almost quantitative conversion. The practically clean and selective formation of ketoses in these reactions, with no detectable admixture of aldoses, stands in stark contrast to the formose reaction, where a complex mixture of linear and branched aldoses and ketoses are produced. These results suggest that the reaction of DHF with aldehydes could constitute a reasonable pathway for the formation of carbohydrates and allow for alternative potential prebiotic scenarios to the formose reaction to be considered.

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Section: Reaction Of Dhf With Glyoxylatementioning

confidence: 99%

Exploratory Experiments on the Chemistry of the “Glyoxylate Scenario”: Formation of Ketosugars from Dihydroxyfumarate

Sagi

Punna

et al. 2012

J. Am. Chem. Soc.

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“…253 Additionally, the β-selectivities observed with the ribose substrate are higher than those attained with the Fischer glycosylation of MeOH. 254,255 …”

Section: 1- Hydroxy Sugar Donorsmentioning

confidence: 99%

Recent Advances in Transition Metal-Catalyzed Glycosylation

2012

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Having access to mild and operationally simple techniques for attaining carbohydrate targets will be necessary to facilitate advancement in biological, medicinal, and pharmacological research. Even with the abundance of elegant reports for generating glycosidic linkages, stereoselective construction of α- and β-oligosaccharides and glycoconjugates is by no means trivial. In an era where expanded awareness of the impact we are having on the environment drives the state-of-the-art, synthetic chemists are tasked with developing cleaner and more efficient reactions for achieving their transformations. This movement imparts the value that prevention of waste is always superior to its treatment or cleanup. This review will highlight recent advancement in this regard by examining strategies that employ transition metal catalysis in the synthesis of oligosaccharides and glycoconjugates. These methods are mild and effective for constructing glycosidic bonds with reduced levels of waste through utilization of sub-stoichiometric amounts of transition metals to promote the glycosylation.

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“…The methyl pentofuranosides were prepared as described earlier (Evdokimov et al, 1999;Wu & Serianni, 1991). Compound (2) crystallized upon cooling of the dry syrup with liquid nitrogen and was recrystallized from dry acetonitrile.…”

Section: Crystalline Furanosidesmentioning

confidence: 99%

Structures of furanosides: geometrical analysis of low-temperature X-ray and neutron crystal structures of five crystalline methyl pentofuranosides

Evdokimov

Gilboa

Koetzle

et al. 2001

Acta Crystallogr B Struct Sci

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Crystal structures of all ®ve crystalline methyl d-pentofuranosides, methyl -d-arabinofuranoside (1), methyl -d-arabinofuranoside (2), methyl -d-lyxofuranoside (3), methyl -dribofuranoside (4) and methyl -d-xylofuranoside (5) have been determined by means of cryogenic X-ray and neutron crystallography. The neutron diffraction experiments provide accurate, unbiased H-atom positions which are especially important because of the critical role of hydrogen bonding in these systems. This paper summarizes the geometrical and conformational parameters of the structures of all ®ve crystalline methyl pentofuranosides, several of them reported here for the ®rst time. The methyl pentofuranoside structures are compared with the structures of the ®ve crystalline methyl hexopyranosides for which accurate X-ray and neutron structures have been determined. Unlike the methyl hexopyranosides, which crystallize exclusively in the C 1 chair conformation, the ®ve crystalline methyl pentofuranosides represent a very wide range of ring conformations.

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d-Penturonic acids: solution studies of stable-isotopically enriched compounds by 1H- and 13C-n.m.r. spectroscopy

Cited by 31 publications

References 23 publications

Exploratory Experiments on the Chemistry of the “Glyoxylate Scenario”: Formation of Ketosugars from Dihydroxyfumarate

Exploratory Experiments on the Chemistry of the “Glyoxylate Scenario”: Formation of Ketosugars from Dihydroxyfumarate

Recent Advances in Transition Metal-Catalyzed Glycosylation

Structures of furanosides: geometrical analysis of low-temperature X-ray and neutron crystal structures of five crystalline methyl pentofuranosides

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