cas 18685-19-3, Methyl-6-O-trityl-2,3,4-tri-O-benzyl-α-D-glucopyranoside

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Synthesis of mannoheptose derivatives and their evaluation as inhibitors of the lectin LecB from the opportunistic pathogen Pseudomonas aeruginosa
Abstract Biofilm formation and chronic infections with Pseudomonas aeruginosa depend on lectins produced by the bacterium. The bacterial C-type lectin LecB binds to the two monosaccharides l-fucose and d-mannose and conjugates thereof. Previously, d-manno
Hofmann, Anna,Sommer, Roman,Hauck, Dirk,Stifel, Julia,G?ttker-Schnetmann, Inigo,Titz, Alexander
p. 34 - 42
(2015)
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Major increases of the reactivity and selectivity in aminoglycoside O-alkylation due to the presence of fluoride ions
Major increases of the selectivity and/or reactivity in aminosugar and sugar O-alkylation were observed in the presence of tetrabutylammonium fluoride (TBAF) in comparison to TBAI under phase-transfer conditions or in solution. The presence of TBAF allowe
Jackowski, Olivier,Bussire, Antoine,Vanhaverbeke, Cécile,Baussanne, Isabelle,Peyrin, Eric,Mingeot-Leclercq, Marie-Paule,Décout, Jean-Luc
p. 737 - 746
(2012)
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USE OF MANNOSE 6 PHOSPHATE AND MODIFICATIONS THEREOF FOR MEMORY ENHANCEMENT AND REDUCING MEMORY IMPAIRMENT
Provided are compositions and methods for memory enhancement, including recovery of memory impairment. The compositions and methods relate to mannose-6-phosphate and derivatives of mannose-6-phosphate. The methods relate to administration of M6P or derivatives thereof to individuals in whom memory enhancement is desired.
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Paragraph 0049; 0058-0060

(2021/06/06)

Chemical synthesis and preliminary biological evaluation of C-6-O-methyl-1-deoxynojirimycin as a potent α-glucosidase inhibitor
A facile and efficient synthesis of 6-O-methyl-1-deoxynojirimycin 4 from commercially available methyl α-D-glucopyranoside in 10 steps and 25% overall yield was reported. The synthetic strategy was based on the regioselective protection/deprotection at 6-
Wang, Lin,Liang, Tingting,Fang, Zhijie
p. 36 - 49
(2019/12/24)

USE OF IGF-2 RECEPTOR AGONIST LIGANDS FOR TREATMENT OF ANGELMAN SYNDROME AND AUTISM
Provided are methods for treatment of neurodevelopmental disorders, such as Angelman Syndrome and autism comprising administering to an individual a composition comprising an agonist ligand of IGF -2 receptor. The agonist ligand of IGF-2 receptor may be IGF -2, or mannose-6-phosphate or a derivative thereof. Compositions comprising mannose-6-phosphate derivatives are also disclosed.
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Paragraph 0062-0063

(2020/02/29)

Peptide-Coated Platinum Nanoparticles with Selective Toxicity against Liver Cancer Cells
Peptide-stabilized platinum nanoparticles (PtNPs) were developed that have significantly greater toxicity against hepatic cancer cells (HepG2) than against other cancer cells and non-cancerous liver cells. The peptide H-Lys-Pro-Gly-dLys-NH2 was identified by a combinatorial screening and further optimized to enable the formation of water-soluble, monodisperse PtNPs with average diameters of 2.5 nm that are stable for years. In comparison to cisplatin, the peptide-coated PtNPs are not only more toxic against hepatic cancer cells but have a significantly higher tumor cell selectivity. Cell viability and uptake studies revealed that high cellular uptake and an oxidative environment are key for the selective cytotoxicity of the peptide-coated PtNPs.
Shoshan, Michal S.,Vonderach, Thomas,Hattendorf, Bodo,Wennemers, Helma
supporting information
p. 4901 - 4905
(2019/01/25)

From d-to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation
Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.
Wan, I. C. Steven,Witte, Martin D.,Minnaard, Adriaan J.
supporting information
p. 7669 - 7673
(2019/10/08)

Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation
A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Br?nsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy hemi-acetals is a potential alternative to the existing cumbersome methods that need specialized handling. The mechanisms for this unique transformation and kinetic/thermodynamic effects have been discussed based on both experimental evidence and theoretical studies.
Ghosh, Titli,Mukherji, Ananya,Srivastava, Hemant Kumar,Kancharla, Pavan K.
supporting information
p. 2870 - 2875
(2018/05/03)

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside
We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.
Xia, Meng-jie,Yao, Wang,Meng, Xiang-bao,Lou, Qing-hua,Li, Zhong-jun
supporting information
p. 2389 - 2392
(2017/05/29)

Study of Uridine 5′-Diphosphate (UDP)-Galactopyranose Mutase Using UDP-5-Fluorogalactopyranose as a Probe: Incubation Results and Mechanistic Implications
Uridine 5′-diphosphate-5-fluorogalactopyranose (UDP-5F-Galp, 7) was synthesized, and its effect on UDP-Galp mutase (UGM) was investigated. UGM facilitated the hydrolysis of 7 to yield UDP and 5-oxogalactose (24), but no 11 was detected. 19F NMR and trapping experiments demonstrated that the reaction involves the initial formation of a substrate-cofactor adduct followed by decomposition of the resulting C5 gem-fluorohydrin to generate a 5-oxo intermediate (10). The results support the current mechanistic proposal for UGM and suggest new directions for designing mechanism-based inhibitors.
Lin, Geng-Min,Sun, He G.,Liu, Hung-Wen
p. 3438 - 3441
(2016/07/26)

Ring-opening polymerization of lactones using binaphthyl-diyl hydrogen phosphate as organocatalyst and resulting monosaccharide functionalization of polylactones
Binaphthyl-diyl hydrogen phosphate has been assessed for the first time as a catalyst for the ring-opening polymerization of ε-caprolactone (CL) and δ-valerolactone (VL). In the presence of benzyl alcohol as coinitiator at 40-60 °C, the polymerization is
Miao, Yong,Phuphuak, Yupin,Rousseau, Cyril,Bousquet, Till,Mortreux, Andre,Chirachanchai, Suwabun,Zinck, Philippe
p. 2279 - 2287
(2013/05/21)

Hydrophobic and hydrophilic balance and its effect on mesophase behaviour in hydroxyalkyl ethers of methyl glucopyranoside
Four series of monosubstituted methyl a-d-glucopyranoside hydroxyal- kyl ethers were prepared and their thermotropic and lyotropic self-organising properties were investigated in terms of the hydrophobic-hydrophilic balance with respect to their molecular
Singh, Madan K.,Xu, Rui,Moebs, Sylvie,Kumar, Anil,Queneau, Yves,Cowling, Stephen J.,Goodby, John W.
p. 5041 - 5049
(2013/06/27)

Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay
In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site.
Rohe, Alexander,Goellner, Christiane,Wichapong, Kanin,Erdmann, Frank,Al-Mazaideh, Ghassab M.A.,Sippl, Wolfgang,Schmidt, Matthias
p. 41 - 48
(2013/04/23)

β-Rhamnosides from 6-thio mannosides
Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cis rhamnosides. The 1,2-cis-selectivity can be rationalized with
Christina, Alphert E.,Es, Daan Van Der,Dinkelaar, Jasper,Overkleeft, Hermen S.,Marel, Gijsbert A. Van Der,Codee, Jeroen D. C.
supporting information; experimental part
p. 2686 - 2688
(2012/04/10)

Highly stereoselective synthesis of primary, secondary, and tertiary α-S-sialosides under lewis acidic conditions
N-Acetyl 4-O,5-N-oxazolidinone protected sialyl phosphates of either anomeric configuration are excellent donors for the formation of α-S-sialosides at -78 °C in dichloromethane with primary, secondary, and tertiary thiols including galactose 3-, 4-, and
Noel, Amandine,Delpech, Bernard,Crich, David
p. 4138 - 4141
(2012/10/07)

Access to new carbohydrate-functionalized polylactides via organocatalyzed ring-opening polymerization
The 4-dimethylaminopyridine (DMAP) catalyzed ring-opening polymerization of lactide using various carbohydrate initiators has been assessed for the functionalization of polylactide. Selectively protected glucose derivatives bearing a free primary alcohol (Glc-1r) and a free secondary alcohol (Glc-2r), glucose and cyclodextrin diol derivatives (Glc-diol and CD-diol), methyl-α-d-glucopyranoside (Glc-Me) and native β-cyclodextrin (CD) were used as initiators. According to the solubility of the carbohydrate derivative, the polymerizations were conducted in chlorinated solvents and in the bulk. Relatively narrow distributions are obtained in high yields in the absence of side reactions, affording a 100% functionalization efficiency. The catalytic synthesis of new carbohydrate link-functionalized polylactides and carbohydrate core star polylactides is reported.
Miao, Yong,Rousseau, Cyril,Mortreux, André,Martin, Patrick,Zinck, Philippe
experimental part
p. 5018 - 5026
(2012/06/29)

Sugar-based peptidomimetics inhibit amyloid β-peptide aggregation
Alzheimer's disease is characterized by the oligomerization and amyloid fibril formation of amyloid β-peptide (Aβ). We describe a novel class of small water-soluble Aβ binding peptidomimetics based on two hydrophobic Ala-Val and Val-Leu dipeptides linked
Dorgeret, Bertrand,Khemtemourian, Lucie,Correia, Isabelle,Soulier, Jean-Louis,Lequin, Olivier,Ongeri, Sandrine
experimental part
p. 5959 - 5969
(2012/01/02)

Efficient synthesis of (6-deoxy-glycopyranosid-6-yl) sulfone derivatives and their effect on Ca2+-ATPase
Synthesis of a series of novel (6-deoxy-glycopyranosid-6-yl) sulfone derivatives has been achieved using a general synthetic strategy. Yields were excellent in every case. The synthetic compounds were evaluated for their biological potential against Casu
Mukherjee, Chinmoy,Ghosh, Swatilekha,Nandi, Pinki,Sen, Parimal C.,Misra, Anup Kumar
scheme or table
p. 6012 - 6019
(2011/01/13)

Efficient syntheses of chiral myo-inositol derivatives-key intermediates in glycosylphosphatidylinositol (GPI) syntheses
A facile and effective method was developed for large-scale syntheses of myo-inositol derivatives with the 1,2,6-O-positions differentiated from each other and from other positions as well. The syntheses started from methyl α-d-glucopyranoside, and the ke
Yu, Fei,Guo, Zhongwu
scheme or table
p. 3852 - 3855
(2010/03/02)

Synthesis of ent-gabosine E from d-mannose by intramolecular nitrone-olefin cycloaddition
Intramolecular nitrone-olefin cycloaddition in a mannose template followed by N-O cleavage, quaternization of the resulting amine, and finally oxidative elimination of the amino group affords, after deprotection, ent-gabosine E in enantiomerically pure form.
Stathakis, Christos I.,Athanatou, Maria N.,Gallos, John K.
scheme or table
p. 6916 - 6918
(2010/05/18)

TOLL-LIKE RECEPTOR 9 AGONISTS
The present invention provides TLR9 agonists comprising, as an active ingredient, a compound represented by formula (I): (wherein a represents 0 or 1; n represents an integer of 0 to 2; m represents an integer of 0 to 5; X1 and X2 each independently represent a hydrogen atom or hydroxy; Y represents an oxygen atom or a sulfur atom; -Q1-represents -O- or the like; -Q2- represents -O- or the like; -Z- represents -O- or the like; R1, R3 and R4 each independently represent hydroxy or the like; R2 and R5 each independently represent a hydrogen atom, hydroxy or the like; and A represents 6-aminopurin-9-yl or the like) or a pharmaceutically acceptable salt thereof, and the like.
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Page/Page column 36; 45

(2009/02/10)

First total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol-a glycoglycerolipid of a marine alga with a high inhibitor activity against human Myt1-kinase
The first total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol, a glycoglycerolipid isolated from a marine alga extract, is described. Starting from α-methylglucopyranoside the multistep strategy allows the stereoselective synthesis of the final compound using various protective group procedures as well as derivatization of partial molecule domains. The latter offers the development of lead structures for inhibitors of human Myt1-kinase.
Goellner, Christiane,Philipp, Claudia,Dobner, Bodo,Sippl, Wolfgang,Schmidt, Matthias
scheme or table
p. 1628 - 1631
(2009/12/09)

Gold mediated glycosylations: Selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety
Selective activation of propargyl 1,2-orthoesters in the presence of propargyl glycosides and propargyl ethers was studied; a catalytic amount of AuBr3 activated the propargyloxy group of the 1,2-orthoester thereby giving access to disaccharide
Sureshkumar, Gopalsamy,Hotha, Srinivas
supporting information; experimental part
p. 4282 - 4284
(2009/03/12)

Do upper limits to the multiple spiro acetalization of the cyclohexane ring exist?
An attempt to transform the pyranoside (5) into the bifaciai ligand (3) is described. The first subtarget is acetal (13) whose conversion into tris acetal (17) is made possible by remote C-H activation. Regrettably, triol (20) does not lend itself to comparable triple cyclization.
Selvaraj, Peter R.,Paquette, Leo A.
scheme or table
p. 165 - 168
(2009/09/08)

Sugar derivatives as new 6-phosphogluconate dehydrogenase inhibitors selective for the parasite Trypanosoma brucei
Sugar derivatives mimicking compounds which take part in the catalysed reaction have been assayed as alternative substrates and/or competitive inhibitors of 6-phosphogluconate dehydrogenase from Trypanosoma brucei and sheep liver. Phosphonate analogues ha
Pasti, Claudia,Rinaldi, Eliana,Cervellati, Carlo,Dallocchio, Franco,Hardre, Renaud,Salmon, Laurent,Hanau, Stefania
p. 1207 - 1214
(2007/10/03)

13C Labelling and electrospray mass spectrometry reveal a de novo route for inositol biosynthesis in Leishmania donovani parasite
In this paper we provide evidence for the presence of a de now route for myo-inositol biosynthesis in the protozoan parasite Leishmania donovani, by the application of 13C labelling and electrospray ionisation mass spectrometry (ESMS). For this myo-[1-13C]inositol is prepared from D-[6-13C]glucose and biosynthetically incorporated in the parasite promastigote cell culture. Biosynthetic phosphatidylinositol (PI) and its hydrolysis products glycero-PI and inositol are analysed by ESMS and the isotopomeric ratio determined. The incorporation experiments show substantial isotopic dilution, indicating the presence of myo-inositol 1-phosphate synthase (MIP synthase) enzyme in the parasite; this is further confirmed by incorporation of D-[6-13C]glucose in the parasite phosphatidylinositol. The Royal Society of Chemistry 2000.
Sahai, Parmeshwari,Chawla, Mamta,Vishwakarma, Ram A.
p. 1283 - 1290
(2007/10/03)

Synthesis of a tetrasaccharide fragment of cobra venom factor oligosaccharide
Synthesis of a tetrasaccharide fragment, α-L-Fuc-(1→3)-β-D-GlcNAc-(1→2)-α-D-Man-(1→6)-α-D-Man-OMe of the cobra venom factor (CVF) oligosaccharide is described. Copyright (C) 1999 Elsevier Science Ltd.
Li, Zhong-Jun,Li, Hui,Cai, Meng-Shen
p. 1 - 7
(2007/10/03)

Synthesis of bile acid 24-acyl glucuronides
The synthesis of acyl glucuronides of common bile acids is described. By means of the Mitsunobu reaction employing diethylazodicarboxylate and triphenylphosphine, bile acids were condensed through the inherent C-24 carboxy group with benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronate, which was prepared from 1-O-methyl-α-D-glucose. The separation and purification of the β2-anomers at the anomeric position of the sugar moiety were attained by preparative thin-layer chromatography and/or high-performance liquid chromatography on a column packed with phenyl-bonded silica using H2O-MeOH as a mobile phase. The removal of the benyl group on the sugar moiety was achieved by catalytic hydrogenation with 10% palladium on carbon to yield the desired acyl glucuronides of bile acids. The structures of these acyl glucuronides were confirmed by proton nuclear magnetic resonance spectral properties.
Goto, Junichi,Murao, Naoaki,Oohashi, Junji,Ikegawa, Shigeo
p. 180 - 185
(2007/10/03)

CDP-6-deoxy-6,6-difluoro-D-glucose: A mechanism-based inhibitor for CDP- D-glucose 4,6-dehydratase [10]
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Chang,Chen,Liu
p. 9698 - 9699
(2007/10/03)

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics
Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.
Jaramillo,Chiara,Martin-Lomas
p. 3135 - 3141
(2007/10/02)

1H- and 13C-NMR spectroscopy of synthetic monosulfated methyl α-D-mannopyranosides
The syntheses of methyl α-D-mannopyranoside 2-, 3-, 4-, and 6-(sodium monosulfate) are presented.The various monosulfated methyl α-D-mannopyranosides have been studied by 1H- and 13C-NMR spectroscopy, affording insight into the 1H- and 13C-shift effects c
Ruiz Contreras, Raphael,Kamerling, Johannis P.,Vliegenthart, Johannes F. G.
p. 85 - 88
(2007/10/02)

SYNTHESIS OF CYTIDINE DIPHOSPHATE-D-QUINOVOSE
The title molecule, cytidine-D-quinovose (CDP-6-deoxy-D-glucose) 1, was synthesized by two different methods from the key intermediate quinovose-1-phosphate 7 which was prepared from glucose.
Liu, Li-da,Liu, Hung-wen
p. 35 - 38
(2007/10/02)

Synthesis of (+)-1,5-dideoxy-1,5-imino-D-galactitol, a potent α-D-galactosidase inhibitor
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Bernotas, Ronald C.,Pezzone, Michael A.,Ganem, Bruce
p. 305 - 311
(2007/10/02)

REDUCTIVE ONE-STEP ELIMINATION OF AN ACETOXYL RESIDUE AT β-POSITION OF A NITRO GROUP: SYNTHESES OF (-)-SHIKIMIC ACID FROM D-MANNOSE AND 2-DEOXYSTREPTAMINE PENTAACETATE FROM N-ACETYL-D-GLUCOSAMINE
By utilizing a reductive one-step elimination reaction of an acetoxyl residue at β-position of the nitro group in cyclitols, a synthesis of the ketocyclitol triacetate (15a), which was already converted to (-)-shikimic acid (16) and (-)-guinic acid (17), from D-mannose (4) and a conversion from N-acetyl-D-glucosamine (18) to 2-deoxystreptamine pentaacetate (22) have been accomplished.
Yoshikawa, Masayuki,Ikeda, Yoshiharu,Kayakiri, Hiroshi,Kitagawa, Isao
p. 209 - 214
(2007/10/02)

SYNTHESIS OF METHYL DERIVATIVES OF URONIC ACIDS. I. SYNTHESIS OF METHYL (METHYL Α-D-GALACTOPYRANOSID)URONATE AND ITS 2-, 3-, AND 4-O-METHYL ETHERS
Alternative unidirectional methods for synthesizing methyl (methyl α-D-galactopyranosid)uronate and its mono-O-methyl ethers by the oxidation (with CrO3-H2SO4-acetone) of the corresponding methyl O-benzyl-O-methyl-α-D-galactopyranosides having unsubstituted 6-OH groups to the corresponding methyl O-benzyl-O-methyl-α-D-galactouronic acids followed by esterification with CH2N2 and the catalytic hydrogenolysis of the benzyl groups are proposed.
Grishkovets, V. I.,Zemlyakov, A. E.,Chirva, V. Ya.
p. 255 - 259
(2007/10/02)