- COMPOSITION COMPRISING SULPHATED GALACTOSE, AND IMPLEMENTATIONS THEREOF
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The present disclosure discloses a composition comprising: (a) at least one sulphated galactose; and (b) at least one saccharide selected from a group consisting of disaccharide, trisaccharide, tetrasaccharide, pentasaccharide, and salts thereof. The pres
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Paragraph 00184; 00185
(2020/06/01)
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- Total synthesis method for xinaomycin
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The invention belongs to the technical field of pharmaceutical chemistry and organic synthesis, and aims to provide a chemical total synthesis method for xinaomycin. The method comprises the steps of:using D-galactose and the like as raw materials, firstly carrying out 8 steps of reactions to obtain a compound 14, then performing condensation on the compound 14 and uracil to obtain a compound 15,performing 4 steps of reactions to obtain a compound 19, performing condensation on the compound 19 and a compound 6 to obtain a compound 20, and finally removing an ester protecting group and a Cbzprotecting group in turn, so as to obtain the natural product xinaomycin. The total synthesis method of the present invention is a method for synthesizing the natural product xinaomycin for the firsttime. The total synthesis method has the advantages of high product purity, low cost, simple operation and the like.
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Paragraph 0033; 0065; 0067; 0068
(2018/05/16)
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- Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives
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We applied a desilylation procedure using SO3H silica gel, with the surface modified by alkylsulfonic acid groups, to silylated sugar, nucleoside, and alkaloid derivatives. The treatment with SO3H silica gel provided desilylated products in good to excellent yield. In the reactions of sugar and nucleoside derivatives, no silyl residue was detected in the crude products, but the crude products of the reaction of alkaloids contained small amounts of silyl residues. Even though the sugar and nucleoside derivatives had a labile glycosyl and C–N bond, respectively, these bonds tolerated the reaction conditions. These outcomes suggested that the desilylation procedure using SO3H silica gel would be applicable to the deprotection of a variety of types of compounds protected by silyl groups. In a gram scale experiment, the desilylation procedure successfully proceeded without the observation of any silyl residue in the crude product.
- Fujii, Hideaki,Shimada, Naoyuki,Ohtawa, Masaki,Karaki, Fumika,Koshizuka, Masayoshi,Hayashida, Kohei,Kamimura, Mitsuhiro,Makino, Kazuishi,Nagamitsu, Tohru,Nagase, Hiroshi
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p. 5425 - 5429
(2017/08/11)
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- Glucose positions affect the phloem mobility of glucose-fipronil conjugates
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In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.
- Lei, Zhiwei,Wang, Jie,Mao, Genlin,Wen, Yingjie,Tian, Yuxin,Wu, Huawei,Li, Yufeng,Xu, Hanhong
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p. 6065 - 6071
(2014/07/21)
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- Glucose positions affect the phloem mobility of glucose-fipronil conjugates
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In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.
- Lei, Zhiwei,Wang, Jie,Mao, Genlin,Wen, Yingjie,Tian, Yuxin,Wu, Huawei,Li, Yufeng,Xu, Hanhong
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p. 6065 - 6071
(2015/04/22)
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- Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models
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Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These
- Pedersen, Christian M.,Olsen, Jacob,Brka, Azra B.,Bols, Mikael
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scheme or table
p. 7080 - 7086
(2011/07/08)
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- Process development of selectively benzoylated and fluorinated glycosyl donors
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Route selection, process development and large-scale preparation of selectively benzoylated and fluorinated d-glucopyranoses, required as glycosyl donors for the synthesis of the SGLT inhibitor SAR7226, are discussed.
- Weiberth, Franz J.,Gill, Harpal S.,Jiang, Ying,Lee, George E.,Lienard, Philippe,Pemberton, Clive,Powers, Matthew R.,Subotkowski, Witold,Tomasik, Witold,Vanasse, Benoit J.,Yu, Yong
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experimental part
p. 623 - 631
(2011/07/30)
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- Regioselective C-6 hydrolysis of methyl O-benzoyl-pyranosides catalysed by candida rugosa lipase
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Hydrolysis of six methyl O-benzoyl-pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C-6, The rate of reaction was dependent on pyra
- Esmurziev, Asian,Sundby, Eirik,Hoff, Bard Helge
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body text
p. 1592 - 1597
(2009/09/08)
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- SYNTHESIS AND USE OF GLYCODENDRIMER REAGENTS
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The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine n a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins. The present invention also relates to synthetic methods for producing thio-glycoses, the thio-glycoses so produced, and to methods for producing glycodendrimer reagents.
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Page/Page column 45; 46
(2010/11/08)
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- Regioselective benzoylation of sugars mediated by excessive Bu2SnO: Observation of temperature promoted migration
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Regioselective benzoylation of carbohydrates using an excess of dibutyltin oxide (Bu2SnO) at increased reaction temperatures has been developed for the synthesis of several glycoside benzoates with one or two free hydroxyl groups, including gal
- Zhang, Zhiyuan,Wong, Chi-Huey
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p. 6513 - 6519
(2007/10/03)
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- A mild and efficient approach for the regioselective silyl-mediated protection-deprotection of C-4 hydroxyl group on carbohydrates
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A regioselective route is reported, which makes the free 4-OH group of hexopyranoses and derivatives easily and rapidly available. This protocol shows high efficiency on intermediates, such as 1a, which contain a TIPS protective group at C-6 and necessarily a benzoyl group at C-4. Treatment of 1a with TBAF cleaves the TIPS protecting group and gives rise to an intramolecular migration of the benzoyl group at C-4 to the less crowded C-6 position.
- Graziani, Andrea,Passacantilli, Pietro,Piancatelli, Giovanni,Tani, Simona
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p. 3857 - 3860
(2007/10/03)
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- Glycosidase-catalysed synthesis of glycosides by an improved procedure for reverse hydrolysis: Application to the chemoenzymatic synthesis of galactopyranosyl-(1 → 4)-O-α-galactopyranoside derivatives
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β-Galactosidase from Aspergillus oryzae, α-galactosidase from Aspergillus niger, β-mannosidase from Helix pomatia and β-glucosidase from almond were used to synthesise different glycosides by reverse hydrolysis: GlcβO(CH2)6OH 1 was o
- Vic, Gabin,Hastings, Jeremy J.,Crout, David H. G.
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p. 1973 - 1984
(2007/10/03)
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- Synthesis of UDP-4-deoxy-4-fluoroglucose and UDP-4-deoxy-4-fluorogalactose and their interactions with enzymes of nucleotide sugar metabolism
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Fluorinated carbohydrates can be used as probes of enzymatic active sites. We report the synthesis of 4-deoxy-4-fluoro-α-D-galactose-1-phosphate and the substrate analogues of UDP-galactose, UDP4-deoxy-4-fluoro-α-D-galactose (UDP-FGal), and of UDP-glucose, UDP-4-deoxy-4-fluoro-α-D-glucose (UDP-FGlc), which may be useful in analyzing the binding properties of enzymes that utilize nucleotide sugars as substrates. As a first step in this study, we determine the kinetic and inhibition parameters for UDP-FGal and UDP-FGlc interacting with UDP-glucose dehydrogenase and UDP-galactose 4-epimerase. UDP-FGlc is a substrate for bovine liver UDP-glucose dehydrogenase: K(m) = 30.2 ± 4.5 μM slightly higher than the value 9.6 ± 0.7 μM for UDP-glucose, and V(m)(UDP-FGlc) = 0.46V(mUDP-Glc). UDP-FGal is not a substrate for UDP-glucose dehydrogenase but is a competitive inhibitor with respect to UDP-glucose (K(i) = 19.9 ± 6.6 μM). These analogs also bind to UDP-galactose 4-epimerase from E. coli with dissociation constants K(d) of 1.4 and 1.1 mM for UDP-FGlc and UDP-FGal, respectively.
- Chapeau,Frey
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p. 6994 - 6998
(2007/10/02)
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- Oxidative Cleavage of 4,6-O-Benzylidene Ring with t-Butyl Hydroperoxide and Copper(II) Chloride. Preparation of Methyl 4-O- and 6-O-Benzoylhexopyranoside Derivatives
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Copper(II) chloride and palladium(II) acetate were found to be highly effective catalysts for oxidative cleavage of O-benzylidene ring with t-butyl hydroperoxide.Using the former catalyst 4,6-O-benzylidenehexopyranoside derivatives were converted into the
- Sato, Ken-ichi,Igarashi, Tetsutaro,Yanagisawa, Yukio,Kawauchi, Nobuya,Hashimoto, Hironobu,Yoshimura, Juji
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p. 1699 - 1702
(2007/10/02)
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- Dioxolanylium Ions Derived from Carbohydrates. IX. Rearrangement between Dioxolanylium and Dioxanylium Ions
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The formation of 4,6-acetoxonium and benzoxonium ion derivatives of methyl gluco-, manno-, galacto- and idopyranosides from the 6-azido-6-deoxy compounds on treatment with nitrosonium ion is described and the formation and rearrangement of the 3,5-benzoxonium ion derived from methyl α-d-xylofuranoside discussed.
- Jacobsen, Steffen
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p. 157 - 164
(2007/10/02)
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- Dioxolanylium Ions Derived from Carbohydrates. VI. Rearrangement of Derivatives of α- and β-Galactopyranosides and Their Reaction with Nucleophiles
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The position of the equilibrium 2->/-3 for a number of 2-phenyl-1,3-dioxolanylium ions, fused to carbohydrates of the galacto and gulo configuration, has been measured in acetonitrile solution.THe anomeric configuration was found to influence both the position of the equilibrium between the benzoxonium ions and the outcome of the trans-opening of the benzoxonium ions with bromine ion.
- Jacobsen, Steffen,Mols, Ole
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p. 163 - 168
(2007/10/02)
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- REGIOSELECTIVE STANNYLATION. ACYLATION OF CARBOHYDRATES: COORDINATION CONTROL
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An efficient method for the regioselective enhancement of the nucleophilicity of polyhydroxy compounds has been developed.Partial stannylation of carbohydrate with (Bu3Sn)2O and subsequent electrophilic attack with benzoyl chloride gave rise to regioselec
- Ogawa, Tomoya,Matsui, Masanao
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p. 2363 - 2370
(2007/10/02)
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