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At least 253 records · Page 14Linked to original sources
PubMed1983

Synthesis of disaccharides related to the O-specific polysaccharide of Salmonella typhimurium.

Methyl 2-O-benzyl-4,6,-O-benzylidene-alpha-D-mannopyranoside (13) has been glycosylated with 3,6-dideoxy-2,4-di-O-p-nitrobenzoyl-alpha-D-xylo-hexopyranosyl bromide (4) and its enantiomer (5) using mercury cyanide as catalyst and toluene and nitromethane as solvent. The anomeric ratio has been determined by 1H NMR spectroscopy and is reversed going from the D to the L compound. Glycosylation of 13 with 2-O-benzyl-3,6-dideoxy-4-O-p-nitrobenzoyl-alph-D-xylo-hexopyranosyl bromide (9) under similar reaction conditions gives exclusively the alpha-linked disaccharide while glycosylation using 2,4-di-O-benzyl-3,6-dideoxy-alpha-D-xylo-hexopyranosyl chloride (12) gives a 1:3 mixture of beta- and alpha-linked disacchrides. Glycosylation of 13 with 12, catalyzed by tetrabutylammonium bromide at elevated temperature, yields exclusively the alpha-linked disaccharide. The conformation of two of the deprotected disaccharides has been determined using hard sphere calculations and high field NMR data.

Carbohydrate Conformation↗
PubMedDate not supplied

[Comparative study of the gastric emptying of disaccharides and their respective monosaccharides in rats with ontogenic lactase deficiency].

In order to evaluate the gastric emptying of disaccharides and their monosaccharides, 64 male, Wistar rats weighing approximately 180 g, were divided into the following eight groups containing eight animals each: maltose, sucrose, lactose, and lactulose, and their correspondent group of monosaccharides: glucose, fructose plus glucose, galactose plus glucose and galactose plus fructose. Each animal received, after a 20 hours fast, 2 ml/100 g weight of a test meal containing a 10% solution of the correspondent sugar and phenol red (6 mg/dl) as a marker. Gastric retention was determined at 10 minutes after orogastric infusion and expressed as a percentage of the infused volume. The observed values (mean +/- SE) of gastric retention (%) of sucrose (35.0 +/- 1.8), lactose (30.4 +/- 1.5), and lactulose (29.5 +/- 1.6) were significantly lower (t test alpha = 0.05), than those observed with their respective monosaccharides, i.e. glucose plus fructose (46.9 +/- 2.6), glucose plus galactose (48.3 +/- 2.4), galactose plus fructose (43.5 +/- 1.5). No difference was noted between gastric retention of maltose (49.9 +/- 4.7) and that of glucose (53.0 +/- 3.0). As far the disaccharides are concerned, statistical analysis (ANOVA followed by Tukey test alpha = 0.05) revealed no differences among the values of gastric retention of sucrose, lactose and lactulose. Gastric retention of maltose was significantly greater than that of the other disaccharides. No differences were found among the gastric retention of monosaccharides.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1988

A monoclonal antibody that recognizes a cluster of a disaccharide, NeuAc alpha(2----6)GalNAc, in mucin-type glycoproteins.

The structure of an epitopic carbohydrate recognized by a monoclonal antibody, MLS 102, was determined. A disaccharide, NeuAc alpha (2----6)GalNAc, the major prosthetic group of ovine submaxillary mucin (OSM) and related synthetic glycosides, NeuAc alpha(2----6)GalNAc alpha----Ser, NeuAc alpha(2----6)GalNAc beta----Ser, and NeuAc alpha (2----6)GalNAc beta----propyl, reacted with MLS 102 to similar extents, but the reaction was considerably weaker compared to that of OSM. This difference in reactivity could be ascribed to the occurrence of a cluster of the disaccharide on OSM. Purification of MLS 102-reactive antigens from a Triton X-100 extract of LS 180 cells by means of immunoaffinity chromatography gave mucin fractions (cMLS 102 antigen) with an OSM-like domain. Correlation between the content of the disaccharide, NeuAc alpha(2----6)GalNAc, in mucins and their reactivity with MLS 102 was observed.

Antigen-Antibody Complex↗
PubMed1975

[Do immunization of rabbits by N-acetylgalactosamine and a disaccharide linked to a protein produce anti-microbial antibodies (author's transl)].

Rabbits were immunized with N-acetylgalactosamine linked to bovalbumine. They produced antibodies which precipitated this same sugar linked to human gamma-globulins but did not agglutinate Salmonella johannesburg which carry a side chain of N-acetylgalactosamine. The same immunization enhanced the titre of "natural" antibodies agglutinating human A red cells (which carry a terminal N-acetylgalactosamine) but they did not evoke such antibodies in rabbits with no "natural" hemagglutinins. These negative results, when compared to the positive one obtained with 0-acetyl-3,6-dideoxygalactose suggest that rabbit antibody-sites limited to one sugar may exist but that they can be detected only under certain conditions. Another group of 8 rabbits was immunized with a disaccharide alpha-Glc-(1 leads to 6)-GalNAc linked to a protein. All produced antibodies agglutinating S. johannesburg (1,40) which carry this disaccharide and S. senftenberg which carry the disaccharide alpha-Glc-(1 leads to 6)-Gal. The titres of these antibodies decreased after a second course of immunization.

ABO Blood-Group System↗
PubMed1996

Analysis of heparin origin by HPLC quantitation of disaccharide components.

A simple method was developed to analyze by high performance liquid chromatography unsaturated disaccharide isomers, derived from heparin by enzymatic digestion. This method was successfully exploited in the investigation of heparin origin. The percent amount of 6-sulphated disaccharides in the heparin extracted from porcine mucosa was found to be higher than that contained in the heparin extracted from bovine mucosa. The differences in the contents of the disaccharides obtained by enzymatic beta-elimination cleavage of heparin were confirmed by 13C-NMR measures of heparin in toto. The processes for extracting and purifying heparin may, however, modify the sulphation pattern of heparin. The structure of the latter seems to depend on the species owing to the specificity of the biosynthesis.

Animals↗
PubMed1997

Automated docking of glucosyl disaccharides in the glucoamylase active site.

To better understand the molecular basis of glucomylase selectivity, low-energy conformers of glucosyl disaccharides obtained from relaxed-residue conformational mapping were flexibly docked into the glucoamylase active site using AutoDock 2.2. This procedure ensures that significant conformational space is searched and can produce bound structures comparable to those obtained by protein crystallography. alpha-Linked glucosyl disaccharides except alpha,alpha-trehalose dock easily into the active site while exclusively beta-linked disaccharides do not, explaining why only the former are glucoamylase substrates. The optimized docking modes are similar at the nonreducing end of the different substrates. Individual atomic energies of intermolecular interaction allow the definite identification of key hydroxyl groups for each substrate. This approach confirmed the versatility of the second subsite of the glucoamylase active site in binding different substrates.

Binding Sites↗
PubMed1998

Intestinal metabolism and transport of alpha-disaccharide conjugates: the role of disaccharidase in the Na+/glucose cotransporter-mediated transport.

Intestinal transport and metabolism of p-nitrophenyl alpha-disaccharides were studied. In the absorption of p-nitrophenyl alpha-melibioside, no compounds other than p-nitrophenyl alpha-melibioside were detected on either the mucosal or the serosal side. In the absorption of p-nitrophenyl alpha-maltoside, on the other hand, p-nitrophenyl alpha-glucoside was formed on the mucosal side to appear on the serosal side. p-Nitrophenol and p-nitrophenyl beta-glucuronide also appeared on the serosal side in the absorption of p-nitrophenyl alpha-maltoside, and the total amount transported to the serosal side was significantly decreased in the absence of Na+ (a cosubstrate of Na+/glucose cotransporter (SGLT1)). Furthermore, the total transport clearance of p-nitrophenyl alpha-glucoside formed from p-nitrophenyl alpha-maltoside on the mucosal side in the p-nitrophenyl alpha-maltoside absorption, was similar to that of the absorption of p-nitrophenyl alpha-glucoside itself. These results led to the conclusion that the intestinal absorption of disaccharide conjugate depended on disaccharidase, and the absorption of the alpha-maltose conjugate occurred sequentially by the maltase-catalyzed hydrolysis of the disaccharide conjugate and SGLT1-mediated transport of the glucose conjugate.

Animals↗
PubMedDate not supplied

Disaccharide conformational flexibility. I. An adiabatic potential energy map for sucrose.

Constrained conformational energy minimizations have been used to calculate an adiabatic (phi, psi) potential energy surface for the disaccharide sucrose. The inclusion of molecular flexibility in the conformational energy analysis of this disaccharide was found to have a significant effect upon the allowed conformational space of the molecule. Three low-energy regions were identified on the adiabatic energy surface, and two of these regions were found to contain two related local minimum-energy conformations, with similar energies, differing only in the directionality of the intra-residue hydrogen bonds of the glucose portion of the molecule. The known crystal structures of seven molecules containing the sucrose moiety all fall within the region of the primary allowed minimum and are consistent with the relaxed energy map, while these crystal conformations could not be rationalized using energy maps for rigid residue geometries. The greater flexibility of the furanoid ring relative to that of the pyranoid ring contributed significantly to the enlargement of the low-energy region on the adiabatic map. However, in spite of the importance of limited flexibility in understanding the conformation and fluctuations of sucrose, this molecule was found to be considerably more rigid that some other disaccharides, such as maltose and cellobiose, in accord with experimental studies.

Carbohydrate Conformation↗
PubMed1977

Synthetic disaccharide-protein antigens for production of specific 04 and 09 antisera for immunofluorescence diagnosis of salmonella.

The synthetic disaccharides abequose 1 leads to a 3 mannose and tyvelose 1 leads to a 3 mannose, representative of Salmonella O-antigen 4 and 9 respectively, were covalently linked to bovine serum albumin (BSA) . Antisera from rabbits immunized with these immunogens were used in indirect immunofluorescence assay for the identification of group B (O-antigen 4) and D (O-antigen 9) Salmonella. A total of 1030 enteric bacterial strains were tested, including 207 group B and 55 group D Salmonella. The anti-abequose-mannose-BSA serum correctly identified all Salmonella group B strains tested. The anti-tyvelose-mannose-BSA serum correctly indentified all Salmonella group D bacteria examined with the exception of 11 of 18 Vi-positive S. typhi strains which did not not stain until the Vi-antigen was removed by boiling. Among the 768 strains representing Salmonella other than groups B and D, E. coli, Shigella, Citrobacter, Klebsiella, Enterobacter, Serratia, Proteus, Vibrio, Pseudomonas, Aeromonas, Yersinia, Bacteroides and Fusobacterium only 5 positive reactions were found. These were observed with Y. pseudotuberculosis strains which have the same disaccharide antigenic determinants as Salmonella O-antigen 4 and 9 respectively. The high specificity of the antisera elicited by the synthetic disaccharide-BSA immunogens make them suitable for a specific and rapid identification of Salmonella bacteria belonging to serogroups B and D.

Animals↗
PubMed1989

T cell line specific for bacterial peptidoglycan subunit: possible role of the COOH-terminal amino acid of the disaccharide tetrapeptide in binding to the T cell receptor.

The T cell line specific for a bacterial cell wall peptidoglycan subunit, disaccharide tetrapeptide of diaminopimelic acid type, was examined for epitope specificity in elicitation of delayed-type hypersensitivity (DTH) in X-irradiated Lewis rats, using pairs of analogs different in optical configuration of the COOH-terminal amino acid. The test cell line induced DTH against analogs with the COOH-terminal D-amino acid but not against those with the L-amino acid at the COOH terminus. A close correlation was found between the T cell line-induced DTH reaction in vivo and the proliferative response in vitro, in terms of clear discrimination of the optical configuration of COOH-terminal amino acid of disaccharide tetrapeptide. The L-isomers (non-stimulatory analogs of T cell proliferation) competitively inhibited the proliferation of the T cell line by the corresponding D-isomers. Thus the L-isomers appear to interact with Ia molecules on antigen-presenting cells. We conclude that COOH-terminal D-amino acid of the disaccharide tetrapeptide could be involved in binding to the T cell receptor, induction of T cell proliferation, and elicitation of DTH.

Amino Acids↗
PubMed1981

Separation of reduced disaccharides derived from glycosaminoglycans by high-performance liquid chromatography.

A high-performance liquid chromatographic (HPLC) method for the analysis of reduced unsaturated disaccharides derived from enzymatic digestion followed by reduction with sodium borohydride of chondroitin sulfates, dermatan sulfate, heparan sulfate and heparin is described. This method is well suited for the HPLC analysis of glycosaminoglycans (GAGs) because the possibility of obtaining anomeric forms of unsaturated disaccharides is eliminated with provides a major advantage for quantitation. This procedure is more sensitive than existing HPLC methods for the determination of enzymatic degradation products from GAGs. In particular, the resolution of disaccharide products from heparan sulfate is improved after reduction. The applicability of this method for the determination of GAGs in biological samples is demonstrated.

Chondroitinases and Chondroitin Lyases↗
PubMed1997

Disaccharide polyphosphates based upon adenophostin A activate hepatic D-myo-inositol 1,4,5-trisphosphate receptors.

The glyconucleotides adenophostin A and B are the most potent known agonists at type 1 inositol trisphosphate [Ins(1,4,5)P3] receptors, although their stuctures differ markedly from that of Ins(1,4,5)P3. Equilibrium competition binding with [3H]Ins(1,4,5)P3 and unidirectional 45Ca2+ flux measurements were used to examine the effects of adenophostin A in hepatocytes, which express predominantly type 2 Ins(1,4,5)P3 receptors. Both Ins(1,4,5)P3 (Kd = 8.65 +/- 0.98 nM) and adenophostin A (Kd = 0.87 +/- 0.20 nM) bound to a single class of [3H]Ins(1,4,5)P3-binding site and each fully mobilized the same intracellular Ca2+ pool; although, adenophostin A (EC50 = 10.9 +/- 0.7 nM) was more potent than Ins(1,4,5)P3 (EC50 = 153 +/- 11 nM). Working on the assumption that it is the phosphorylated glucose component of the adenophostins that mimics the critical features of Ins(1,4,5)P3, we synthesized various phosphorylated disaccharide analogs containing this structure. The novel disaccharide-based analogs, sucrose 3,4,3'-trisphosphate [Sucr(3,4,3')P3], alpha,alpha'-trehalose 3,4,3',4'-tetrakisphosphate [Trehal(3,4,3',4')P4], alpha,alpha'-trehalose 2,4,3', 4'-tetrakisphosphate [Trehal(2,4,3',4')P4], and methyl 3-O-(alpha-d-glucopyranosyl)-beta-d-ribofuranoside 2,3', 4'-trisphosphate [Rib(2,3',4')P3], were all able to mobilize the same intracellular Ca2+ pool as Ins(1,4,5)P3 and adenophostin A; although, none was as potent as adenophostin A. The rank order of potency of the analogs, adenophostin A > Ins(1,4,5)P3 approximately Rib(2,3',4')P3 > Trehal(2,4,3',4')P4 > Glc(2',3,4)P3 approximately Trehal(3,4,3',4')P4 > Sucr(3,4,3')P3, was the same in radioligand binding and functional assays of hepatic Ins(1,4,5)P3 receptors. Both Rib(2,3',4')P3, which was as potent as Ins(1,4,5)P3, and Trehal(2,4,3',4')P4 bound with significantly higher affinity ( approximately 27 and approximately 3-fold, respectively) than the only active carbohydrate agonist of Ins(1,4,5)P3 receptors previously examined [Glc(2',3,4)P3]. We conclude that phosphorylated disaccharides provide novel means of developing high-affinity ligands of Ins(1,4,5)P3 receptors.

Adenosine↗
PubMed1998

Straightforward Synthesis of (1-->2)-Linked Pseudo Aza-C-disaccharides by the Novel Cycloaddition of Enantiopure Cyclic Nitrones to Glycals.

The novel, highly stereoselective, intermolecular cycloaddition reaction of enantiopure cyclic nitrones 8 to 1,2-glycals 9 opens the way to a straightforward synthesis of a broad class of new (1-->2)-linked pseudo aza-C-disaccharides 6, suitable substrates for selective inhibition of glycosidase enzymes. The cycloadditions occur with high stereocontrol, displaying preferential interaction between the bottom face of the glycal and the face of the nitrone anti to the substituent on C-3, with the reagents approaching in an exo fashion. The cycloadditions produced tricyclic isoxazolidines 7 that represent nonreducing pseudo aza-C-disaccharides stable to hydrolytic conditions. The target pseudo aza-disaccharides 6 were obtained by sequential deprotection of the hydroxyl groups and isoxazolidine ring-opening.

Journal Article↗
PubMed1999

Disaccharide esters screened for inhibition of tumor necrosis factor-alpha release are new anti-cancer agents.

Tumor necrosis factor-alpha (TNF-alpha) is a proinflammatory cytokine playing a part in various pathological states. Non-toxic inhibitors of TNF-alpha release are thought to be promising agents for cancer prevention. We found that the acetone fraction of the tobacco leaf surface lipid containing glucose esters and sucrose esters inhibited both TNF-alpha release from BALB/3T3 and KATO III cells induced by okadaic acid and tumor promotion by okadaic acid on mouse skin initiated with 7,12-dimethylbenz(a)anthracene (DMBA). Next, we investigated the inhibition of TNF-alpha release with synthetic disaccharide esters, such as 6,6'-di-O-alkanoyl-alpha, alpha-trehaloses (6,6'-diester-trehaloses), 4,4'-di-O-alkanoyl-alpha, alpha-trehaloses (4,4'-diester-trehaloses) and 6,6'-diamino-6,6'-dideoxy-N,N'-dialkanoyl-alpha, alpha-trehaloses (6,6'-diamide-trehaloses) bearing fatty acids of various chain lengths, and n-dodecyl-beta-D-maltoside as a disaccharide monoester. 6,6'-Diester-trehaloses and 4,4'-diester-trehaloses of C8 to C12 fatty acids, 6,6'-diamide-trehaloses of C8 to C14 fatty acids, and n-dodecyl-beta-D-maltoside all inhibited TNF-alpha release in a dose-dependent manner. The IC50 values are 7.4-14.8 microM for 6,6'-diester-trehaloses (C8 to C12), 14.6-21.6 microM 4,4'-diester-trehaloses (C8 to C12), 2.9-15.0 microM for 6,6'-diamide-trehaloses (C8 to C14) and 23 microM for dodecyl-beta-D-maltoside. Both 6,6'-di-O-octanoyl-alpha, alpha-trehalose (C8, designated as SS555) and n-dodecyl-beta-D-maltoside (C12) inhibited tumor promotion by okadaic acid on mouse skin initiated with DMBA. Percentages of tumor-bearing mice in week 15 of tumor promotion were reduced from 60.0 to 13.3 with SS555, and to 46.7 with n-dodecyl-beta-D-maltoside. Moreover, SS555 inhibited TNF-alpha gene expression mediated through inhibition of AP-1 activation, but not NF-kappa B activation. This paper reports that diester-trehaloses of C8 to C12 fatty acids and mimics of disaccharide monoesters such as n-dodecyl-beta-D-maltoside appear to be potential cancer-preventive agents of a new type.

3T3 Cells↗
PubMedDate not supplied

Moderate disaccharide malabsorption does not affect weight gain and cecal cell proliferation in piglets.

BACKGROUND: Intestinal malabsorption of disaccharides or oligosaccharides occurs normally in preterm infants, the majority of the world's adult population when ingesting dairy products, and in sick patients with abnormal intestinal motility or intestinal damage. Although there may be benefit to colonic fermentation, there also could be mucosal damage from excessive fermentation. Moreover, excess fluid in the colon also may impair fermentation. There are few data that address the effects of moderate amounts of carbohydrate, such as 50% of intake, reaching the colon. We addressed the hypothesis that normal weight gain and stool characteristics would occur during disaccharide malabsorption approximating 50% of intake. METHODS: Twelve piglets (aged 17 days) were randomized to receive control sow milk replacement formula (CON; lactose 60 g/L) or CON modified so that lactulose replaced 50% of the lactose (LAC). During a 5- to 7-day period, weight gain and fecal characteristics were observed before autopsy for cecal histology and determination of cecal cell proliferation using bromodeoxyuridine. RESULTS: Neither group developed diarrhea. In LAC and CON, formula intakes (g/kg/d) were similar (279 +/- 30 and 280 +/- 35), as were the ratios of weight gain:formula intake (g/mL): 0.23 +/- 0.04 and 0.22 +/- 0.04. Mean cecal cell proliferation was not diminished in the group receiving lactulose (p > .05). CONCLUSION: These data suggest that moderate (50%) disaccharide malabsorption per se does not cause diarrhea and does not impair dietary energy use or colonic cell proliferation.

Animals↗
PubMed1991

Synthesis and biological activities of lipid A analogs: modification of a glycosidically bound group with chemically stable polar acidic groups and lipophilic groups on the disaccharide backbone with tetradecanoyl or N-dodecanoylglycyl groups.

Six novel lipid A analogs were synthesized. The first two analogs, 4 and 5, have an alpha-glycosidically bound carboxymethyl or 1,3-dicarboxyisopropyl group on the disaccharide backbone with four tetradecanoyl groups. The next three analogs, 6, 7 and 8, have two or four N-dodecanoylglycyl groups on the 1-alpha-O-phosphonooxyethylated disaccharide backbone. Analog 6 bears N-dodecanoylglycyl groups on the hydroxyl functions at positions 3 and 3', and tetradecanoyl groups on the amino functions at positions 2 and 2'. Analog 7 is a 2, 3, 2' and 3'-tetrakis(N-dodecanoylglycyl) derivative, and analog 8 resembles compound 6, but the binding of the N-dodecanoylglycyl and tetradecanoyl groups at positions 2, 2' and 3, 3' are reversed. The third analog, 9, has the same acyl group configuration as compound 6, but has a 1,3-dicarboxyisopropyl group at position C-1. Compounds 4 and 5 exhibited definite antitumor activity against Meth A fibrosarcoma, indicating that the phosphate group at the C-1 position in lipid A could be replaced by the carboxylic acid without reducing the antitumor activity. In rabbits, compounds 6 and 9 exhibited potent antitumor activity, but their toxicity was extremely low. On the other hand, compounds 7 and 8 showed no antitumor activity. The levels of antitumor activity of 6 and 9 were similar to those of the natural-type lipid A. The antitumor activities of analogs with a N-dodecanoylglycyl group on the disaccharide backbone depended on the connecting sites of the acyl groups.

Animals↗
PubMed1998

Conformational changes due to vicinal glycosylation: the branched alpha-L-Rhap(1-2)[beta-D-Galp(1-3)]-beta-D-Glc1-OMe trisaccharide compared with its parent disaccharides.

Conformations of the alpha-L-Rhap(1-2)-beta-D-Glc1-OMe and beta-D-Galp(1-3)-beta-D-Glc1-OMe disaccharides and the branched title trisaccharide were examined in DMSO-d6 solution by 1H-nmr. The distance mapping procedure was based on rotating frame nuclear Overhauser effect (NOE) constraints involving C- and O-linked protons, and hydrogen-bond constraints manifested by the splitting of the OH nmr signals for partially deuteriated samples. An "isotopomer-selected NOE" method for the unequivocal identification of mutually hydrogen-bonded hydroxyl groups was suggested. The length of hydrogen bonds thus detected is considered the only one motionally nonaveraged nmr-derived constraint. Molecular mechanics and molecular dynamics methods were used to model the conformational properties of the studied oligosaccharides. Complex conformational search, relying on a regular phi, psi-grid based scanning of the conformational space of the selected glycosidic linkage, combined with simultaneous modeling of different allowed orientations of the pendant groups and the third, neighboring sugar residue, has been carried out. Energy minimizations were performed for each member of the phi, psi grid generated set of conformations. Conformational clustering has been done to group the minimized conformations into families with similar values of glycosidic torsion angles. Several stable syn and anti conformations were found for the 1-->2 and 1-->3 bonds in the studied disaccharides. Vicinal glycosylation affected strongly the occupancy of conformational states in both branches of the title trisaccharide. The preferred conformational family of the trisaccharide (with average phi, psi values of 38 degrees, 17 degrees for the 1-->2 and 48 degrees, 1 degree for the 1-->3 bond, respectively) was shown by nmr to be stabilized by intramolecular hydrogen bonding between the nonbonded Rha and Gal residues.

Carbohydrate Sequence↗
PubMed2000

Total synthesis of everninomicin 13,384-1--Part 4: explorations of methodology; stereocontrolled synthesis of 1,1'-disaccharides, 1,2-seleno migrations in carbohydrates, and solution- and solid-phase synthesis of 2-deoxy glycosides and orthoesters.

Methods for the stereocontrolled construction of 1,1'-disaccharides, 2-deoxy glycosides, and orthoesters are reported. Specifically, a tin-acetal moiety was utilized to fix the anomeric stereochemistry of a carbohydrate acceptor leading to an efficient and stereoselective synthesis of 1,1'-disaccharides, while a newly discovered 1,2-phenylseleno migration reaction in carbohydrates opened entries to 2-deoxy glycosides and orthoesters. Thus, reaction of 2-hydroxy phenylselenoglycosides with DAST led to 2-phenylselenoglycosyl fluorides which reacted with carbohydrate acceptors to afford, stereoselectively, 2-phenylselenoglycosides. The latter compounds could be reductively deselenated to 2-deoxy glycosides or oxidatively converted to orthoesters via the corresponding ketene acetals.

Aminoglycosides↗