Showing papers on "Aldose published in 1986"
111 citations
TL;DR: In this article, pairs of enantiomers of nine aldoses were separated on gas-liquid chromatography equipped with an SE-30 capillary column as trimethylsilyl ethers after conversion of the aldosing to methyl 2-(polyhydroxyalkyl)-thiazolidine-(4R)-carboxylates using the reaction with L-cysteine methyl ester.
Abstract: Pairs of enantiomers of nine aldoses were separated on gas-liquid chromatography equipped with an SE-30 capillary column as trimethylsilyl ethers after conversion of the aldoses to methyl 2-(polyhydroxyalkyl)-thiazolidine-(4R)-carboxylates using the reaction with L-cysteine methyl ester.
105 citations
101 citations
Patent•
03 Nov 1986TL;DR: In this article, a heterocyclic oxophthalazinyl acetic acid having aldose reductast inhibitory activity of the formula "STR1##", where X is oxygen or sulfur; Z is a covalent bond, O, S, NH or CH2 or CHR5 Z is vinyl; R1 is hydroxy, or a prodrug group; R2 is a hetercyclic group, R3 and R4 are hydrogen or the same or a different substituent, and R5 is hydrogen, methyl or trifluoromet
Abstract: A heterocyclic oxophthalazinyl acetic acid having aldose reductast inhibitory activity of the formula ##STR1## wherein X is oxygen or sulfur; Z is a covalent bond, O, S, NH or CH2 or CHR5 Z is vinyl; R1 is hydroxy, or a prodrug group; R2 is a heterocyclic group, R3 and R4 are hydrogen or the same or a different substituent, and R5 is hydrogen, methyl or trifluoromethyl The pharmaceutically acceptable acid addition salts of the above compounds wherein R1 is di(C1 -C4)alkylamino or (C1 -C4)alkoxy substituted by N-morpholino or di(C1 -C4)alkylamino and the pharmaceutically active base addition salts of the above compounds wherein R1 is hydroxy are also aldose reductase inhibitors
68 citations
55 citations
TL;DR: The reagent chloro-β-cyanoethyl-N,N-diisopropylamino-phosphoramidite reacts smoothly with the anomeric hydroxyl group of a properly protected (benzyl) α-L-fucopyranose to afford a relatively stable phosphite intermediate in high yield.
53 citations
52 citations
TL;DR: Aldose reductase inhibitors produced no effect in altering the rate of Nitro Blue Tetrazolium formation from either glucose or xylose, indicating that the observed inhibition in vitro does not result from a free-radical-scavenger effect.
Abstract: The production of polyols in vitro by highly purified aldose reductase (EC 1.1.1.21) was monitored by g.l.c. In the presence of NADPH aldose reductase reduced glucose, galactose and xylose to the respective polyols sorbitol, galactitol and xylitol. The rates of formation of these polyols closely mirrored the Km values for the substrates obtained from kinetic measurements that monitored the rate of disappearance of NADPH. No polyol production occurred in the absence of purified aldose of purified aldose reductase, and analysis by g.l.c. revealed only the presence of unchanged monosaccharides. Addition of the aldose reductase inhibitor sorbinil to purified rat lens aldose reductase incubated with xylose in the presence of NADPH resulted in decreased xylitol production. However, aldose reductase inhibitors produced no effect in altering the rate of Nitro Blue Tetrazolium formation from either glucose or xylose, indicating that the observed inhibition in vitro does not result from a free-radical-scavenger effect.
47 citations
40 citations
TL;DR: In this paper, the 20- and 19-hydroxy metabolites of 12(S)-HETE were synthesized using readily available, chiral precursors, including chiral derivatives.
37 citations
TL;DR: The diastereoisomeric, 4-O-phosphono-D-glucosamine derivatives named in the title have been synthesized, starting from benzyl 2-amino-2-deoxy-4,6-O -isopropylidene-beta-D -glucopyranoside and (3RS)-3-hydroxytetradecanoic acid.
TL;DR: Cell-free extracts of Bacillus subtilis contain enzyme activities which catalyze an acyloin-type condensation reaction (carboligase reaction) resulting in the formation of 1-deoxy-ketoses, a precursor of biosynthesis of thiazole ring of thiamine.
Abstract: Cell-free extracts of Bacillus subtilis contain enzyme activities which catalyze an acyloin-type condensation reaction (carboligase reaction) resulting in the formation of 1-deoxy-ketoses. The reactions are deduced to proceed as follows: pyruvate + aldose →C02 + 1-deoxy-ketose (I)acetoin + aldose →acetaldehyde + 1-deoxy-ketose (II)methylacetoin + aldose →acetone + 1-deoxy-ketose (III)Experiments with mutants of B. subtilis defective in pyruvate dehydrogenase (PDH) or acetoin dehydrogenase (AccDH) and with partially purified enzyme preparations revealed that PDH (EC 1.2.4.1) catalyzes reaction (I), and AccDH catalyzes reactions (II) and (III).That the PDH purified from Escherichia coli and the PDC purified from bovine heart also catalyzed reaction (I) indicates that 1-deoxy-ketose-forming activities are widely distributed. One of the reactions catalyzed by these enzymes is the formation of 1-deoxy-d-threo-pentulose, a precursor of biosynthesis of thiazole ring of thiamine.
TL;DR: A simple and effficient preparation of β-hydroxy esters with a well-defined stereochemistry has been developed using 3-bromoisoxazolines as key-intermidiates.
TL;DR: Aldoses are rapidly epimerized at C-2 in the presence of [Ni(H2O)2(tmen)2]Cl2(Tmen = N,N,N′-trimethylethylenediamine) and, of the two C-II ions, nickel(II) ions form complexes with only the mannose-type epimers (D-mannose, D-lyxose, and D- or L-rhamnose) stereoselectively.
Abstract: Aldoses are rapidly epimerized at C-2 in the presence of [Ni(H2O)2(tmen)2]Cl2(tmen =N,N,N′-trimethylethylenediamine) and, of the two C-2 epimers, nickel(II) ions form complexes with only the mannose-type epimers (D-mannose, D-lyxose, and D- or L-rhamnose) stereoselectively.
TL;DR: The treatment of acetobromoglucose with N,N-dimethylformamide dialkyl acetals in the presence of tetra-n-butylammonium bromide affords the corresponding 1,2-exo-alkyl orthoacetates in a pure form and in almost quantitative yields as mentioned in this paper.
TL;DR: In this paper, four 2,6-dideoxyhexoses; D-(+)-digitoxose, D-(−)-cymarose, O(−)-olivose and O( −)-oleandrose have been synthesized stereo and enantio- selectively starting with (+)-(2R,3S)-1,2-epoxypent-4-en-3-ol prepared by asymmetric epoxidation of divinylcarbinol.
TL;DR: The D-ribose or D-erythrose derived acyclic synthon, which possesses a 2-malonyl carbon chain at C-1 position, was cyclized stereoselectively to a six or five-membered carbocycle as discussed by the authors.
Abstract: The D-ribose or D-erythrose derived acyclic synthon, which possesses a 2-malonyl carbon chain at C-1 position, was cyclized stereoselectively to a six- or five-membered carbocycle. Those carbocycles were converted into pseudo-β-L-mannopyranose derivatives or pseudo-β-L-arabinofuranose derivatives efficeintly.
TL;DR: In this paper, two alternative strategies for the synthesis of quinuclidines from hexoses are outlined, one of which is employed in an enantiospecific synthesis of S-quinuclidinol whereby a two carbon fragment is introduced at C-4 of D-glucose.
TL;DR: Monosaccharide O-thioformates under thermal or high-pressure conditions react with various dienes to give Othiopyran-2-yl saccharides.
TL;DR: Synthese a partir du D-arabinose des hydroxy-8S, (-11S, -9S et -12S) eicosatetraene-5,9,11,14oates de methyle
Abstract: Synthese a partir du D-arabinose des hydroxy-8S, (-11S, -9S et -12S) eicosatetraene-5,9,11,14oates de methyle