Showing papers on "Aldose published in 1989"
TL;DR: Southern hybridization analysis of human genomic DNA indicates a multigene system for aldose reductase, suggesting the existence of additional proteins, and the aldo-keto reductases superfamily of proteins may have a more significant and hitherto not fully appreciated role in general cellular metabolism.
434 citations
TL;DR: Synthese d'oligosaccharides a partir de tri-O-benzyl-3,4,6 glucal, de di-Obenzoyl- 3,4 glucal et d'hexofuranoses ou dhexopyranoses proteges as mentioned in this paper.
Abstract: Synthese d'oligosaccharides a partir de tri-O-benzyl-3,4,6 glucal, de di-O-benzoyl-3,4 glucal et d'hexofuranoses ou d'hexopyranoses proteges
152 citations
94 citations
TL;DR: A partir de penta-O-acetyl mannopyranose, synthese stereoselective du squelette dipyranno [2,3-b:2',3'-e]pyranne de la brevetoxine β
Abstract: A partir de penta-O-acetyl mannopyranose, synthese stereoselective du squelette dipyranno [2,3-b:2',3'-e]pyranne de la brevetoxine β
89 citations
TL;DR: In this paper, alcohols are converted into allyl ethers under neutral conditions, using allyl ethyl carbonate in the presence of a catalytic amount of palladium (0).
75 citations
TL;DR: Le meilleur cocatalyseur est l'(acetoxy trimethyl) stannane as discussed by the authors, i.e., l'acetate de trimethylsilylmethyl-2 allyle, utilise comme precurseur du trimethylenemethane
Abstract: Le meilleur cocatalyseur est l'(acetoxy trimethyl) stannane. L'acetate de trimethylsilylmethyl-2 allyle est utilise comme precurseur du trimethylenemethane
69 citations
TL;DR: Investigation of the distribution of NADPH-dependent reductase activity in the rat cortex, outer medulla and inner medulla was investigated through biochemical and histochemical methods and a similar immunohistochemical distribution was also observed in the human kidney with antibodies against human placental aldose reduct enzyme.
68 citations
TL;DR: The data show that human muscle is a new and relatively rich source of a monomeric NADPH/NADH reductase which is clearly identifiable as aldose reduct enzyme.
65 citations
54 citations
TL;DR: In this article, the ketones (+)-1 and (−)-1 were derived from furan and 1-cyanovinyl (1S)-camphanate, respectively.
Abstract: (1S, 4R, 5S, 6S)-5-exo, 6-exo-(Isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one ((−)-1) was transformed with high stereoselectivity to L-allose. Similarly, enantiomer (+)-1 was transformed into L-talose. The ketones (+)-1 and (−)-1 were derived from furan and 1-cyanovinyl (1S)-camphanate and 1-cyanovinyl (1R)-camphanate, respectively.
48 citations
TL;DR: Synthese de S-ethyl-1 tetra-O-acetyl-2,3,4,6 hexopyranoside a partir de per-Oacetylhexopyranose et d'ethanethiol et en presence de chlorure de zirconium.
TL;DR: In this paper, the use of an inverted RAMA catalyst for the reduction of the ketone in this class of carbohydrates to an alcohol has been discussed, where the structure of this aldose and the location of the vicinal diol formed in the aldol reaction can be control led through the structure in R'. The ketone group derived from the DHAP offers control of the chemistry at the end of the sugar distal to the aldehyde.
Abstract: t'\"0:'\":\" group at C2 rather than an aldehyde group at C I . Conversion of a ketose to an aldose is not straightforward.T Here we descr ibe a new st ra tegy for us ing RAMA ( the \" inver ted\" s t ra teg) . Scheme I ) that increases the usefu lness of th is enzyme as a cata lys t in the synthes is o f sugars . We a lso demonst ra te the va lue of r id i to l dehydrogenase ( lDH) as a catalyst for the diastereospecif ic reduction of the ketone in this class of carbohydrates to an alcohol.8'e RAMA-catalyzed aldol condensation between DHAP and a half-protected dialdehyde, OCHR'(CHg;n, generates a protected aldose having a ketone (that derived from DHAP) at Cn-,. Dephosphorylat ion. reduction. or other transformation of the ketone and deprotect ion o f the a ldehyde prov ide the a ldose. Both the structure of this aldose and the location of the vicinal diol formed in the aldol reaction can be control led through the structure of R'. The ketone group derived from the DHAP offers control of the chemistry at the end of the sugar distal to the aldehyde. Scheme II i l lustrates this * inverted\" approach to the synthesis of sugars us ing RAMA wi th syntheses of t -xy lose (4) and 2deoxy-o-ar abi no-hexose (9). RAMA-cata lyzed (50 un i ts ) condensat ion o f d ie thoxyacet a ldehyde ( l ) r0 ( l mmol . added in f ive por t ions over 5 days) and of ructose 1,6-d iphosphate (1 mmol) in the presence of t r iosephosphate isomerase (EC 5.3.1 .1 , ca. 200 un i ts ) , fo l lowed by treatment in situ with acid phosphatase (AP, 20 units), afforded 2 in 60Vo overal l yield. 'r Conversion of ketone 2 (1 mmol) to alcohol 3 with L stereochemistry was accomplished in 69Vo yield, using IDH (from Condida utilis,l0 units),e coupled with formate dehydrogenase (FDH, 10 units) and sodium formate (3 mmol)
TL;DR: In this paper, 2,3,5-tetra-O-acetyl-4-deoxy-4-(methoxyphosphyl and phenylphosphinyl)-D-ribofuranoses, whose structures and 3T2 (and 2T3) conformations were established by spectroscopy.
Abstract: Methyl 2,3-O-isopropylidene-β-D-ribopyranoside gave efficiently (in 4 steps) methyl 4-deoxy-4-[dimethoxyphosphinyl and (methoxy)phenylphosphinyl]-2,3-O-isopropylidene-β-D-ribopyranosides (ca. 30% overall yield). These were led (in 2–3 steps) to the title compounds and then converted into 1,2,3,5-tetra-O-acetyl-4-deoxy-4-(methoxyphosphinyl and phenylphosphinyl)-D-ribofuranoses, whose structures and 3T2 (and 2T3) conformations were established by spectroscopy.
TL;DR: In this paper, ten homologous series (n-butyl through n-decyl) of aldose S,S-acetals (D-glucose, D-galactose and D-mannose) have been prepared.
Abstract: Ten homologous series (n-butyl through n-decyl) of aldose S,S-acetals (D-glucose, D-galactose, D-mannose, L-rhamnose, 2-deoxy-D-glucose, D-xylose, D-lyxose, D- or L-arabinose, D-ribose and 2-deoxy-D-ribose) have been prepared. Most of these compounds form thermotropic liquid crystals, the exceptions being the entire L-rhamnose series and some of the derivatives with the shortest alkyl chains. All of the compounds have been investigated with differential scanning calorimetry and polarization microscopy. Some temperature dependent powder X-ray data are also presented. A model is proposed which correlates the carbohydrate configuration with the melting behaviour. On the basis of now available behaviourial characteristics, visual inspection, mixing experiments and precedent, the mesophase is identified as smectic Ad, the partially overlapping carbohydrate moieties being in the centre and the aliphatic chains pointing outward at an angle of about 62°. Despite the intrinsic chirality of all the carbohy...
TL;DR: In this paper, the one pot conversion of 1,2,4,6-tetra-0,acetyl-β-D-glucopyranose, 1, into phenyl 2,4-6-tri-0-acetyl 3,0-trialkylsilyl-1,thio-β-,D-Glucopyanides, 3, is described.
TL;DR: The arylation of 3-O-methyl-1,2-O -isopropylidene-α -D-xylo-pentodialdofuranose (2) at the aldehyde centre by means of bromonagnesium or triisoproytitanium salts of phenols 1 provides a simple access to 5-C arylxylofuranoses 3 and 4 of either L-ido or D-gluco configuration as discussed by the authors.
TL;DR: In this article, the Wittig-Horner reaction was used in the synthesis of C-glycosides and α and β glycosyl acetates of the 2,3,4,6-tetra-O-benzyl-D-mannopyranose and 2, 3, 4, 6, 6-Tetra O-Benzylglucopyrinose.
Abstract: The synthetic utility of the Wittig-Horner reaction in the synthesis of C-glycosides is illustrated by the preparation of the α-and β-glycosyl acetates of the 2,3,4,6-tetra-O-benzyl-D-mannopyranose and of the 2,3,4,6-tetra-O-benzylglucopyranose. A partial epimerization of the C-2 carbon of the starting protected carbohydrate is observed.
TL;DR: A variety of benzylated 1-OH derivatives, having an acetyl or an allyl group, were synthesized from the corresponding protected 2-methoxyethyl glycosides through a brief treatment with TiCl4 in dichloromethane and a subsequent hydrolysis of the intermediary 1-Cl derivatives on a silica-gel column.
Abstract: A variety of benzylated 1-OH derivatives, having an acetyl or an allyl group, of D-glucose, D-galactose, D-mannose, D-xylose, L-arabinose, L-fucose, and L-rhamnose, were synthesized from the corresponding protected 2-methoxyethyl glycosides through a brief treatment with TiCl4 in dichloromethane and a subsequent hydrolysis of the intermediary 1-Cl derivatives on a silica-gel column.
TL;DR: Trans-addition of iodoazide to the double bond of 3,4,6-tri-O -acetyl-1,5-anhydro-d - arabino -hex-1-enitol yielded 2-deoxy-2-iodoglycosyl azides, which are precursors of 1,2- trans -2-amino-2deoxyglycopyranosides when treated by an alcohol in the presence of triphenylphosphine as mentioned in this paper.
TL;DR: In this paper, O-protected 3,4-O-isopropylidene-β-d-galactopyranosides with tert-BuOK in N,N-dimethylformamide or methyl sulfoxide produces 4-deoxy-α-l-threo-hex-4-enopyranoides in good yields.
TL;DR: The first synthesis of the title compounds 8 and 10 was accomplished by a multi-step approach involving prior preparation of a suitably protected fluorosugar 6, 7, 8 and 9 as mentioned in this paper.
TL;DR: In this article, the synthesis of 2S,3R,4R)-2-hydroxymethyl-3,4-pyrrolidinediol and 4-acetamido-1,2,3-tri-O-acetyl-4-deoxy-L-xylopyranose were attained in four steps from Dmannose, using iron(III)-catalyzed photoreaction as a key reaction.
Abstract: (Synthesis of 2S,3R,4R)-2-hydroxymethyl-3,4-pyrrolidinediol and 4-acetamido-1,2,3-tri-O-acetyl-4-deoxy-L-xylopyranose were attained in four steps from D-mannose, using iron(III)-catalyzed photoreaction as a key reaction.
TL;DR: In this article, the cycloaddition of tosyl isocyanate to sugar vinyl ethers followed by N-deprotection affords β-lactams with fairly good asymmetric induction.
Patent•
17 May 1989
TL;DR: Aldose reducing enzyme inhibitor capable of preventing and treating complication of diabetes mellitus is described in this paper, using 6H-Dibenzo[b,d]pyran-6-one derivative expressed by formula IV (X 1 to X 8 are H, Cl, lower alkyl, lower alkoxy or OH and at least one among X 1 to x 8 is OH) is subjected to sulfur esterification or glycolic acid etherification.
Abstract: NEW MATERIAL:A compound expressed by formula I [R 1 to R 8 are H, Cl, lower alkyl, lower alkoxy, formula II or formula III (M is H, alkali metal or ammonium) and at least one among R 1 to R 8 is formula II or formula III]. EXAMPLE: 6H-Dibenzo[b,d]pyran-6-one-3-sulfuric acid ester potassium salt. USE: An aldose reducing enzyme inhibitor capable of preventing and treating complication of diabetes mellitus. PREPARATION: A hydroxy-6H-dibenzo[b,d]pyran-6-one derivative expressed by formula IV (X 1 to X 8 are H, Cl, lower alkyl, lower alkoxy or OH and at least one among X 1 to X 8 is OH) is subjected to sulfur esterification or glycolic acid etherification, or a substance subjected to the abovementioned esterification or etherification is reacted with a substance capable of producing alkali metal ion or ammonium ion. COPYRIGHT: (C)1990,JPO&Japio
TL;DR: In this article, the authors propose an addition de composes dieniques conjugues: obtention des oses correspondants substitues O-[thiopyrane-2-carbonyl]
Abstract: Addition de composes dieniques conjugues: obtention des oses correspondants substitues O-[thiopyrane-2-carbonyl]
TL;DR: In this paper, the stereoselective C(4) alkylations of 6-exo,7-Exo-(isopropylidenedioxy)-2,8-dioxabicyclo[3.2.1] octan-3-one with Mel and PhCH2OCH2Br are presented; the products so-obtained have been converted to partially protected 5,6-dideoxy-5-C-methyl-D,L-ribo-hexofuranose and 5-deoxy -5
Abstract: The stereoselective C(4) alkylations of 6-exo,7-exo-(isopropylidenedioxy)-2,8-dioxabicyclo[3.2.1]octan-3-one with Mel and PhCH2OCH2Br are presented; the products so-obtained have been converted to partially protected 5,6-dideoxy-5-C-methyl-D,L-ribo-hexofuranose and 5-deoxy-5-C-methyl-D,L-talo-hexofuranose.
TL;DR: Among the test compounds, the compounds having a carboxymethylsulfamoyl group at the 3- or 4-position exhibited the greatest inhibitory potency, and structure-activity trends of the tested compounds are discussed.
Abstract: Various benzo[b]futran derivatives with a carboxymethylsulfamoyl group were prepared and evaluated for aldose reductase-inhibitory potency. Most of the compounds displayed significant inhibitory activities (IC50, 10-8-10-7M). Among the test compounds, the compounds having a carboxymethylsulfamoyl group at the 3- or 4-position exhibited the greatest inhibitory potency. Structure-activity trends of the tested compounds are discussed.
TL;DR: In this paper, the diacetates 8 and 9 of 2,3-dideoxy-D-pentofuranose and -pentopyranose are synthesized.