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  • Articles  (125)
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  • Articles  (125)
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  • 1
    Electronic Resource
    Electronic Resource
    Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens (1993)
    s.l. : American Chemical Society
    The @journal of organic chemistry 58 (1993), S. 1090-1099 
    Details
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jo00057a021
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  • 2
    Electronic Resource
    Electronic Resource
    TROPHIC AND CYTOPROTECTIVE NUTRITION FOR INTESTINAL ADAPTATION, MUCOSAL REPAIR, AND BARRIER FUNCTION (2003)
    Palo Alto, Calif. : Annual Reviews
    Annual Review of Nutrition 23 (2003), S. 229-261 
    Details
    ISSN: 0199-9885
    Source: Annual Reviews Electronic Back Volume Collection 1932-2001ff
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract Intestinal epithelial cell turnover (proliferation, migration, differentiation, and apoptosis) and gut barrier functions are dynamic processes that are markedly affected by nutritional status, the route of feeding, and the adequacy of specific nutrients in the diet. Emerging studies are defining potential therapeutic roles for specific nutrients and diet-derived compounds (including arginine, glutamate, glutamine, glutathione, glycine, vitamin A, zinc, and specific lipids) in gut mucosal turnover, repair, adaptation after massive bowel resection, and barrier function. The role and regulation of endogenous bowel flora in generating short-chain fatty acids from diet-derived fiber and other diet-derived compounds and the effects of these agents on gut function are increasingly being elucidated. Results of these investigations should define new nutritional methods for trophic and cytoprotective effects on the intestine in conditions such as inflammatory bowel disease, malnutrition, and short bowel syndrome.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1146/annurev.nutr.23.011702.073036
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  • 3
    Electronic Resource
    Electronic Resource
    Amino acids. 8. A novel synthesis of .gamma.-carboxy-L-glutamic acid from L-5-oxoproline esters (1990)
    s.l. : American Chemical Society
    The @journal of organic chemistry 55 (1990), S. 3064-3067 
    Details
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jo00297a022
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  • 4
    Electronic Resource
    Electronic Resource
    Rhizobial saccharides. Part. 4. Unusual Reactivity of Pyruvated Glycosyl Donors during construction of rhizobial exopolysaccharide fragments (1997)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 339 (1997), S. 534-540 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two pyruvated galactosyl donors, 2,3-di-O-benzoyl-4,6-O-[1-(R)-methoxycarbonyl(ethylidene)]-α-D-galactopyranosyl chloride (6) and trichloroacetimidate 13, were coupled to position 3 of suitably protected mono and disaccharide benzyl glucoside acceptors. For both donors, an unusual high content of the α-(1 → 3)-linked products was obtained. The corresponding β-(1 → 3)-linked di- and trisaccharides are related to exopolysaccharides of Rhizobium leguminosarum.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19973390196
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  • 5
    Electronic Resource
    Electronic Resource
    Enolether, XVIII Eine einfache Synthese von Cumarinen (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 373-378 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: In boiling 1,2-dichloroethane 3-ethoxyacryloyl chloride (1) reacts with phenols 2 to yield 3-ethoxyacrylates 3, which by treatment with conc. sulfuric acid/10% SO3 cyclize to give coumarins 9 in good yields. The methoxy-substituted compounds 3d and 3k do not react to coumarins 9 with H2SO4/SO3 but with POCl3/H2O at room temperature.
    Notes: Aus 3-Ethoxyacryloylchlorid (1) und Phenolen 2 entstehen in siedendem 1,2-Dichlorethan 3-Ethoxyacrylsäure-arylester 3, die sich mit konz. H2SO4/10% SO3 bei 0°C in guten Ausbeuten zu Cumarinen 9 cyclisieren lassen. Die 3-Ethoxyacrylsäure-methoxy-phenylester 3d und 3k cyclisieren unter diesen Bedingungen nicht, lassen sich jedoch mit POCl3/H2O bei Raumtemperatur ebenfalls in guten Ausbeuten in die entsprechenden Cumarine 9d und 9k überführen.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200320
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  • 6
    Electronic Resource
    Electronic Resource
    Enolether, XIII. Die Acylierung von Enolethern mit reaktiven Carbonsäure-chloriden (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 2766-2782 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Enol Ethers, XIII. Acylation of Enol Ethers with Reactive Carbonyl ChloridesEnol ethers 2 are acylated under mild conditions with activated acyl chlorides, e.g. chloroacetyl chlorides 1a, b, cyanoacetyl chloride (6c), and malonic acid chlorides 6a,b in good yields. The products formed and the yield depend on the acylation potential of the acyl chlorides. The potential β-keto aldehydes 4, 5, and 1,3,5-tricarbonyl compounds 8 obtained are valuable intermediates for heterocyclic synthesis.
    Notes: Enolether 2 lassen sich mit aktivierten Säurechloriden wie den Chloressigsäurechloriden 1a und 1b, Cyanacetylchlorid (6c) oder Malonylchloriden 6a, b unter milden Bedingungen in guten Ausbeuten acylieren. Die Abhängigkeit der Produktbildung und der Ausbeuten vom Acylierungspotential der eingesetzten Säurechloride wird aufgezeigt. Die erhaltenen potentiellen β-Ketoaldehyde 4, 5 bzw. 1,3,5-Tricarbonylverbindungen 8 sind wertvolle Zwischenprodukte für die Synthese von Heterocyclen.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150809
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  • 7
    Electronic Resource
    Electronic Resource
    Enolether, XVI. Synthese von 4-Hydroxy-2H-pyran-2-onen (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 741-752 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Enol Ethers, XVI. Synthesis of 4-Hydroxy-2H-pyran-2-onesEnol ethers 1 are acylated by malonyl dichlorides 2 to yield pentanoic acid derivatives 3; cyclisation of 3 with conc. sulfuric acid/10% SO3 results in the formation of 6-unsubstituted 4-hydroxy-2H-pyran-2-ones 4. The formation of pyrylium salts is decisive for the avoidance of side reactions. Spectroscopic investigations establish the structure of the compounds 4 as α-pyran-ones B.
    Notes: Enolether 1 werden mit Malonyldichloriden 2 zu Pentansäurederivaten 3 acyliert, deren Cyclisierung mit konz. Schwefelsäure/10% SO3 zu in 6-Stellung unsubstituierten 4-Hydroxy-2H-pyran-2-onen 4 führt. Die Bildung von Pyryliumsalzen ist entscheidend für die Vermeidung von Nebenreaktionen. Spektroskopische Untersuchungen beweisen das Vorliegen der Verbindungen 4 in der angegebenen α-Pyranon-Struktur B.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180233
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  • 8
    Electronic Resource
    Electronic Resource
    Unexpected Formation of 3,6-Anhydrofuranoses by Acid Treatment of Methyl 2,3-Di-O-acyl-D-glycopyranosides (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 255-260 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Furanoses, 3,6-anhydro ; Glycosides, pyruvylated ; Anhydrofuranoses ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Treatment of methyl 2,3-di-O-acyl-D-glycopyranosides 1 of glucose and mannose with catalytic amounts of trifluoromethanesulfonic acid afforded the corresponding bis(5-O-acyl-3,6-anhydro-D-glycofuranose) 1,2′:2,1′-dianhydrides 6 in 12-58% yield the structure of which was confirmed for the α-D-glucose derivative 6a by an X-ray analysis. In addition, in the presence of methyl pyruvate (2a) or methyl 2-acetoxy-acrylate (2b) various amounts of diastereomeric 3,6-anhydro-5-O-benzoyl-1,2-O-(1-methoxycarbonyl)ethylidene-α-D-glucofuranoses 5 and acylated methyl α-D-glucopyranosides 3 and 4, respectively, were formed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930145
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  • 9
    Electronic Resource
    Electronic Resource
    The 2-(Chloroacetoxymethyl)benzoyl (CAMB) Group as a Novel Protecting Group for Carbohydrates (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 659-664 
    Details
    ISSN: 0170-2041
    Keywords: Glycosylations ; Protecting groups ; Benzoyl, 2-chloroacetoxymethyl- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The application of the 2-(chloroacetoxymethyl)benzoyl (CAMB) group to the O-protection of position 2 in glycosyl donors is described. Saponification of the phthalide and subsequent chloroacetylation of 2-(hydroxymethyl)benzoic acid (1) gave 2-(chloroacetoxymethyl)benzoic acid (2). Treatment of 2 with thionyl chloride afforded the acyl chloride 3. Acylation of O-2 of 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (4a), galactopyranose (4b) and of the amino group of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose (4c) afforded the fully protected pyranose derivatives 5a-c in high yields. Compounds 5a and 5b were converted with HBr in acetic acid into the corresponding 2-O-CAMB-protected bromides 6a, b in excellent yields. Silver trifluoromethanesulfonate promoted glycosylation of the latter with 2-hydroxyethyl benzoate yielded the β-glycosides 8a (74%) and 8b (69%). Direct activation of the glucosamine derivative 5c with ferric chloride gave the glucoside 8c (54%). Furthermore, the galactosyl bromide 6b was coupled with methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside (11) affording the 2′-O-CAMB-protected methyl glycoside disaccharide 12 (63%). Similarly, condensation of the glucosyl bromide 6a with 4a gave the β-(1→2)-linked disaccharide 13 (45%). Treatment of compounds 8a and 13 with thiourea resulted in the deblocked glycosides 9a and 14. Similar deprotection of 8b gave 2-benzoyloxyethyl 3,4,6-tri-O-acetyl-β-D-galactopyranoside (9b) and the 2-O-[2-(hydroxymethyl)benzoyl] derivative 10. Reaction of 8c with thiourea afforded solely the dechloroacetylated glucoside 9c.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940704
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  • 10
    Electronic Resource
    Electronic Resource
    Preparation of Diastereomeric 3,4-O-Pyruvate Acetal-Containing D-Galactopyranose Derivatives, Structural Assignment and Use for Oligosaccharide Synthesis (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 859-866 
    Details
    ISSN: 0170-2041
    Keywords: Galactosides, 3,4-pyruvylated ; Oligosaccharides ; Carbohydrates ; Escherichia coli ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Treatment of phenyl 1-thio- and allyl 2,6-di-O-benzoyl-D-galactopyranosides 3 with methyl pyruvate and BF3 · Et2O in various solvents gave 1,6-anhydro-3,4-di-O-benzoyl-2-deoxy-2-phenylthio-β-D-idopyranose (4) and the corresponding diastereomers of 3,4-O-pyruvate acetal-containing galactosides 5. The phenyl 1-thio-β-galactoside R-5a and the allyl a-galactoside R-5b were both converted into methyl 3,4-O-[1-(R)-(methoxycarbonyl)ethylidene]-β-D-galactopyranoside (9), the structure of which as well as that of 4 was confirmed by X-ray crystallography. Compound R-5a was converted into 5-[(benzyloxycarbonyl)amino]pentyl 6-O-benzoyl-3,4-O-[1-(R)-(methoxycarbonyl)ethylidene]-β-D-galactopyranoside (18) by using the (2-chloroacetoxymethyl)benzoyl (CAMB) group for the temporary protection of position 2. Glucosamination of 18 and subsequent deblocking of the intermediate disaccharide gave β-D-GlcpNAc-(1→2)-3,4-(S)-pyruvate-β-D-Galp-O(CH2)5NH2 (21) which represents a fragment of the Escherichia coli K 47 polysaccharide.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940903
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