- Fingerprint-detection of sugar-binding proteins generated by labeled structured glycopeptides arrays
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Based on a novel biochip-concept involving labeled structured peptides and the "protein-fingerprint" method, the construction of O-glycopeptide-array on a novel chip material and their use for biodetection are described.
- Kawasaki, Takayasu,Ohyama, Takafumi,Hirata, Akiyoshi,Nokihara, Kiyoshi
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- Laxative Metabolites from the Leaves of Moringa oleifera
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Three new flavonoids, quercetin-3-O-6-[methyl-(S)-3-hydroxy-3-methylglutaroyl(1→6]-β-d-glucopyranoside (1), kaempferol-3-O-[methyl-(S)-3-hydroxy-3-methylglutaroyl(1→6)]-β-d-glucopyranoside (2), and quercetin-3-O-6-[(E)-4-methoxy-5-methylhexa-2,4-dienoatyl(1→6)]-β-d-glucopyranoside (3), and two new alkaloids, 5-dehydroxymethyl-pyrrolemarumine 4″-O-α-l-rhamnopyranoside (4) and N1-methyl-N2-((4-O-α-l-rhamnopyranoside)benzyl) oxalamide (5), together with 45 known compounds (6-50) were isolated from the leaves of Moringa oleifera Lam. Among those compounds, 1-octacosanol (50), a straight-chain 28-carbon alcohol, exhibited good activity against diphenoxylate-induced constipation in mice, which is obtained as a laxative constituent from the plant for the first time. In order to have an accurate understanding of the content of compound 50, a quantification with gas chromatography-tandem mass spectrometry (GC-MS/MS) was carried out. The anti-inflammatory and α-glucosidase inhibitory activity of some compounds also was assessed.
- Huang, Xiang-Zhong,Jiang, Meng-Yuan,Li, Yan-Hong,Lu, Huai,Pu, Xiao-Yun,Tian, Kai,Wang, Wei,Xiong, Yong
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- Viridaphin A1 glucoside, a green pigment possessing cytotoxic and antibacterial activity from the aphid Megoura crassicauda
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A green pigment, viridaphin A1 glucoside (1), was isolated from the green aphid Megoura crassicauda. One- and two-dimensional NMR spectrometric analyses of 1 and its aglycone established the structure as an octacyclic compound. Viridaphin A1 glucoside exhibited cytotoxicity against HL-60 human tumor cells with an IC50 of 23 μM and antibacterial activity against Bacillus subtilis NBRC 3134 with a minimum inhibitory concentration of 10.0 μg/mL. These results suggested that aphid pigments may protect aphids from invasive species, including viruses and bacteria.
- Horikawa, Mitsuyo,Hoshiyama, To-Sho,Matsuzawa, Masako,Shugyo, Takanori,Tanaka, Masami,Suzuki, Shinya,Sato, Masao,Ito, Takuya,Asakawa, Yoshinori,Kaku, Hiroto,Nishii, Takeshi,Inai, Makoto,Takahashi, Shigeru,Tsunoda, Tetsuto
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- Efficient synthesis of L-galactose from D-galactose
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Racemic protein crystallography is an emerging methodology to obtain high-resolution protein structures. Preparation of both a mirror image of protein and a mirror image of glycan is essential to apply the new methodology to glycoprotein. This article describes an efficient synthesis of L-galactose that is amirror image of D-galactose. The developed method takes only 6 steps from D-galactose without any chromatographic purification.
- Orii, Ryo,Izumi, Masayuki,Kajihara, Yasuhiro,Okamoto, Ryo
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p. 560 - 566
(2016/04/19)
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- A comparative study of the neutral and acidic polysaccharides from Allium macrostemon Bunge
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Neutral and acidic polysaccharides, named AMP40N and AMP40S respectively, were isolated and purified from the dried bulbs of Allium macrostemon Bunge. Both of them showed a single and symmetrically sharp peak, indicating they were homogeneous polysaccharides. Molecular weights of AMP40N and AMP40S were determined to be 18.2 and 105.1 kDa, respectively. AMP40N was composed of arabinose and glucose, while AMP40S was composed of rhamnose, arabinose, glucose and galactose and a certain amount of uronic acid. FT-IR, periodic acid oxidation, Smith degradation, methylation and GC-MS analysis revealed that non-reducing terminal and →2,6)-Glc-(1→ existed in AMP40N and AMP40S. The glycosidic linkage of arabinose in AMP40N was →2)-Ara-(1→, whereas it was Ara-(1→ in AMP40S. AMP40S had (1→2)-linked l-rhamnose residue. Both AMP40N and AMP40S exhibited strong anti-tumor potential against human gastric carcinoma cells BGC-823, in particular, AMP40S presented significantly higher inhibitory rate of 85.94% than AMP40N of 52.63%.
- Zhang, Zhanjun,Wang, Fuhua,Wang, Mingchun,Ma, Liping,Ye, Hong,Zeng, Xiaoxiong
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p. 980 - 987
(2015/01/09)
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- Synthesis of peracetylated C-1-deoxyalditol- and C-glycoside-dipyrranes via dithioacetal derivatives
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Dipyrranes bearing peracetylated mono- or disaccharidic C-1-deoxyalditol moieties were prepared from d-galactose, d-glucose, d-mannose, and lactose. A partially hydrolyzed polysaccharide (agarose) was also used as starting material for the synthesis of a disaccharide-containing C-glycoside dipyrrane. These compounds were synthesized as follows: the sugar starting materials were first submitted to a mercaptolysis-acetylation one-pot procedure (EtSH/HCl-Ac 2O/pyridine). The resulting peracetylated diethyl dithioacetals were converted into dipyrranes through carbonyl deprotection (H5IO 6, THF-Et2O) followed by TFA-catalyzed pyrrole condensation with yields up to 62%. Overall yields from sugar starting materials were up to 49%.
- Ló, Stephanie M.S.,Cunico, Juliana C.,Ducatti, Diogo R.B.,Orsato, Alexandre,Duarte, M. Eugênia R.,Barreira, Sandra M.W.,Noseda, Miguel D.,Gon?alves, Alan G.
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supporting information
p. 1137 - 1140
(2013/05/08)
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- Indiosides G-K: Steroidal glycosides with cytotoxic and anti-inflammatory activities from Solanum violaceum
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Five new steroidal glycosides (1-5) and nine known compounds were isolated from Solanum violaceum. Indiosides G (1) and H (2) are spirostene saponins with an iso-type F ring, indioside I (3) is a spirostane saponin, and indiosides J (4) and K (5) are unusual furostanol saponins with a deformed F ring. These structures represent rare naturally occurring steroidal skeletons. The structures of the new compounds were elucidated using 1D and 2D spectroscopic techniques and acid hydrolysis. Compounds 2, 3, and 7-9 exhibited cytotoxic activity against six human cancer cell lines (HepG2, Hep3B, A549, Ca9-22, MDA-MB-231, and MCF-7) with IC50 values of 1.83-8.04 μg/mL. Steroidal saponins 3, 8, and 9 showed inhibitory effects on superoxide anion generation with IC50 values of 2.84 ± 0.18, 0.62 ± 0.03, and 1.62 ± 0.59 μg/mL, respectively. Saponins 8 and 9 also inhibited elastase release with IC50 values of 111.05 ± 7.37 and 4.04 ± 0.51 μg/mL, respectively. Structure-activity relationship correlations of these compounds with respect to cytotoxic and anti-inflammatory effects are discussed.
- Yen, Chiao-Ting,Lee, Chia-Lin,Chang, Fang-Rong,Hwang, Tsong-Long,Yen, Hsin-Fu,Chen, Chao-Jung,Chen, Shu-Li,Wu, Yang-Chang
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experimental part
p. 636 - 643
(2012/06/30)
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- 1,2;3,4-Di-O-isopropylidene-l-galactose synthesis from its d-enantiomer
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Easy procedure was devised to obtain di-O-isopropylidene-l-galactose from di-O-isopropylidene-d-galactose.
- Doboszewski, Bogdan,Herdewijn, Piet
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experimental part
p. 2253 - 2256
(2012/05/20)
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- VO(acac)2/H2O2/NaI: A mild and efficient combination for the cleavage of dithioacetal derivatives of sugars
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A wide variety of dithioacetal derivatives of sugars can be cleaved easily into the corresponding open-chain aldehydo sugars using an efficient combination of VO(acac)2/H2O2/NaI at 0-5 °C. Some of the salient features of this protocol are mild reaction conditions, good yields, short reaction times, easy work-up procedures, and non-involvement of toxic chemicals.
- Khan, Abu T.,Ali, Shahzad,Sidick Basha,Khan, Md. Musawwer,Lal, Mohan
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experimental part
p. 2629 - 2632
(2011/12/04)
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- ALKYL H-PHOSPHONATES OF N,N'-DIALKYLIMIDAZOLIUMS AND OF QUATERNARY AMMONIUMS AND USES THEREOF
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The application relates to the use of a salt associating an ammonium cation with an alkyl H-phosphonate anion of the following formula (I) in which R is a hydrocarbon radical, the pointed bond can be present or not, the radical R3 being then present or absent, as an ionic liquid. The ammonium cation is preferably an imidazolium cation. This ionic liquid is particularly useful in the field of green chemistry as a substitute for organic solvents. The application also relates to a method for preparing such a salt by the direct dealkylation of the corresponding dialkylphosphite by the appropriate nitrated base, in one step and without any solvent. The application also relates to a method for preparing mixed methylated phosphites.
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Page/Page column 8
(2010/06/11)
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- 1-Benzenesulfinyl piperidine (BSP)/triflic anhydride: An effective combination for the hydrolysis of dithioacetals
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The combination of 1-benzenesulfinyl piperidine and triflic anhydride, in conjunction with an aqueous workup, hydrolyses a broad range of dithioacetals to the corresponding carbonyl compounds under very mild, non-oxidative conditions.
- Crich, David,Picione, John
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p. 1257 - 1258
(2007/10/03)
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- Labeled nucleosides and method for their preparation
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The invention relates to a method for the chemical preparation of labeled nucleosides via an oxidative-ring-opening step and a reductive-ring-closure step starting from a labeled D-glucose nucleoside resulting in the corresponding D-ribose-nucleoside by removing the carbon atom 3 on the glucose and comprising the steps of:1. a protection of the sugar ring hydroxyl groups,2. a sugar-base condensation, whereby the base is a purine or a pyrimidine,3. a deprotection of the sugar ring hydroxyl groups,4. an oxidative-ring-opening and removal of the carbon atom 3, and5. a reductive-ring-closure resulting in labeled D-ribose-nucleoside.The invention further relates to a compound obtainable via the method according to the invention having the formula selected from [13C,15N] labeled 6'-O-mono- or 6'-O-bis-C1-C6-alkyloxytrityl-D-glycopyranosyl nucleosides, or [13C,15N] labeled tetra-O-acetyl-D-glycopyranosyl nucleosides or [13C,15N] labeled glycopyranosyl nucleosides.
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- Liquid-Crystalline D-Glucose Dialkyl Acetals and Dodecyl D-Glucofuranosides
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Two new systems of liquid crystalline glucose derivatives 5a-d, 6a, b are prepared, studied and compared with reference compounds.The α- and β-D-dodecyl glucofuranosides 6a, b show smectic A phases.The clearing points of the furanosides are of the same magnitude as those of the pyranosides.The alkyl glucose acetals 5a-d show columnar discotic phases.The clearing points are about 30 deg C lower than those of the corresponding thioacetals. - Key Words: Acetals / Amphiphiles / Carbohydrates / Glucosides / Liquid crystals
- Tietze, Lutz F.,Boege, Kai,Vill, Volkmar
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p. 1065 - 1068
(2007/10/02)
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- Phyllanthostatin A
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An unusal cytostatic (PS ED50 4 ug/ml) lignan ester has been isolated from the Central American tree Phyllanthus acuminatus and is herein designated Phyllanthostatin A. Separation of a methanol extract of the root by size exclusion chromatography, high speed countercurrent distribution and semi-preparative hplc afforded glycoside in 0.007% yield. In solution, phyllanthostatin A was slowly transformed into justicidin-B. The structure of the lignan glycoside, determined by hrfabms and 2D nmr spectroscopy, is: STR1
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- Synthesis of L-gulose, L-galactose, and their acetylated aldehydo forms from 6-S-phenyl-6-thio-D-hexoses
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Methyl 6-S-phenyl-6-thio-α-D-glucopyranoside, prepared in high yield from methyl α-D-glucopyranoside by the action of diphenyl sulfide and tributylphosphine in pyridine, was converted into 6-S-phenyl-6-thio-D-glucitol pentaacetate (7) by sequential hydrolysis, borohydride reduction, and acetylation.Oxidation of 7 with 3-chloroperoxybenzoic acid gave the corresponding S-epimeric sulfoxides, which underwent Pummerer rearrangement to 1-epimeric L-gulose S-phenyl monothiohemiacetal hexaacetates.Boron trifluoride-catalyzed reaction of the latter with thiophenol gave theanalogues diphenyl dithioacetal, whereas base-catalyzed methanolysis led to free L-gulose.Treatment of 7 with N-chlorosuccinimide afforded 1-epimeric 1-chloro-1-S-phenyl-1-thio-L-gulitol pentaacetates, which were hydrolyzed to provide aldehydo-L-gulose pentaacetate.The same reaction sequences were performed with 6-S-phenyl-6-thio-D-galactose, synthesized in two steps from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, furnishing ultimately L-galactose, its diphenyl dithioacetal pentaacetate, and aldehydo-L-galactose pentaacetate.Similar reaction sequences for the chain-terminal interchange of oxidation state in other ω-S-phenyl-ω-thioaldoses may prove useful for the preparation of less-common sugar derivatives.
- Gonzalez, Francisco Santoyo,Baer, Hans H.
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- PYRIDINDOLOL ANALOGUES. SYHTHESIS OF 3-HYDROXYMETHYL-1-(POLYHYDROXYALKYL)-β-CARBOLINES
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Peracetylated (D)-glucose, (D)-galactose, (D)-ribose, (L)-arabinose and (D)-xylose have been subjected to a Pictet-Spengler cyclisation with methyl tryptophanate to give β-carboline derivatives which have been converted to a series of pyridindolol analogues.
- Willard, Nico P.,Dorland, Erwin,Pandit, Upendra K.
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p. 1549 - 1556
(2007/10/02)
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- The Anodic Deprotection of the Carbonyl Group Applied to Dethioacetalisation of Oses
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The anodic method of deprotection of carbonyl compounds (oxidative decomposition of gem-dithioacetal systems) is applied with success to sugars.Protected hydroxy groups like esters and cyclic acetals are not affected.
- Lebouc, Alain,Simonet, Jacques,Gelas, Jacques,Dehbi, Abdellatif
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p. 320 - 321
(2007/10/02)
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- REMOVAL OF SUGAR DITHIOACETAL GROUP WITH N-BROMOSUCCINIMIDE
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Oxidative removal of the dithioacetal group of several protected sugar and 2-acylamido-2-deoxy sugar dialkyl dithioacetals with N-bromosuccinimide in 97percent aqueous acetone or 1:1 (v/v) 2-methyl-2-propanol-acetone was compared with removal with mercury dichloride-mercury(II) oxide or mercury dichloride-cadmium carbonate.In general, removal with N-bromosuccinimide proceeded more rapidly, and, with one exception, yields higher than or equal to those obtained with the method using mercury salt.
- Miljkovic, Momcilo,Dropkin, Daniel,Hagel, Peter,Habash-Marino, Margaret
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- Conversion of iridoids to prostaglandins
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Naturally occurring iridoids provide the starting material for a unique synthesis sequence to produce prostaglandin intermediates. The iridoid lactone is hydrogenated, converted to an acetal, and rings opened to introduce the carbonyl octenyl side chain in six steps. The intermediate can be converted to prostaglandin as previously demonstrated.
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- STRUCTURE OF A NEW CYANOGLUCOSIDE FROM ILEX WARBURGII LOESN.
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A cyanoglucoside (1) has been isolated from the fruits of Ilex warburgii Loesn., and its structure has been elucidated by chemical and spectral means as (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile.A related compound, Menisdaurin (3) was also isolated.
- Ueda, Katsuhiro,Yasutomi, Kazuko,Mori, Iwao
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p. 149 - 150
(2007/10/02)
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- 1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose
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The title compound 13 is prepared on different routes from suitable benzyl derivatives with gluco-configuration.Preparations use the susceptibility of axial 5-O-benzyl groups in this compounds to selective hydrogenolysis, thus allowing subsequent inversion of configuration in this position from D-gluco to L-ido by an oxidation/reduction sequence.Only 0.08percent of 13 are found in the equilibrium mixture of idose in acidic medium.It is shown with 4-C-methyltalose as example, that the amount of 1,6-anhydrofuranoses in these equilibria rises significantly by changing the hydroxy groups in 4-position from secondary to tertiary ones.
- Koell, Peter,John, Hans-Georg,Schulz, Juergen
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p. 613 - 625
(2007/10/02)
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