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  • Chemistry  (26)
  • Computer Programming and Software  (2)
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  • 1995-1999  (16)
  • 1985-1989  (12)
  • 1
    Digitale Medien
    Digitale Medien
    Literaturkarussell. Chemie (1996)
    Weinheim : Wiley-Blackwell
    Chemie in unserer Zeit 30 (1996), S. X 
    Details
    ISSN: 0009-2851
    Schlagwort(e): Chemistry ; Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/ciuz.19960300214
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  • 2
    Digitale Medien
    Digitale Medien
    Biosynthesis of Homoterpenes in Higher Plants (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 247-253 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: In higher plants, the two homoterpenes 4,8-dimethyinona-1,3,7-triene (1) and 4,8,12-trimethyltrideca-1,3,7,11-tetraene (2) are synthesized from the regular terpene alcohols nerolidol and geranyllinalool by fragmentation into the homoterpene and butenone. The biosynthetic pathway is evidenced by conversion of (2H)nerolidol in Hoya purpureo-fusca, Magnolia liliiflora nigra, Robinia pseudoacacia, and Philadelphus coronarius.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19890720208
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  • 3
    Digitale Medien
    Digitale Medien
    Synthesis of Chiral 12-Phenyl(2H)dodecanoic Acids: Useful metabolic probes for the biosynthesis of 1-alkenes from fatty acids (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 917-928 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The synthesis of chiral 12-phenyi(2H)dodecanoic acids as metabolic probes for the evaluation of the stereo-chemical course of the biosynthesis of 1-alkerses from fatty acids in plants and insects is described. The diastereoisomeric (2R, 3R)- or (2S, 3S)-12-phenyl(2,3-2H2)dodecanoic acids 11 are obtained in high chemical and optical yield (〉97% e.e.) from the readily available (E)-12-phenyl(2,3-2H2)dodec-2-enoic acid (10) or (E)-12-phenyldodec-2-enoic acid (10a) by microbial reduction with wet packed cells of Clostridium tyrobutyricum in either 2H2O or H2O buffer. (2R)- and (2S)-12-phenyl(2-2H)dodecanoic acids 9 (〉97% e.e.) are accessible from the allylic alcohol 6 via Sharpless epoxidation with (+)-L- or (-)-D-diethyl tartrate, Synthetic routes to the (E)- and (Z)-11-phenyl(1-2H) undec-1-enes 16 and 16a as reference compounds are also included.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19890720507
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  • 4
    Digitale Medien
    Digitale Medien
    Über die Biosynthese von γ-Dodecanolacton in reifenden Früchten: Aroma-Komponenten der Erdbeere (Fragaria ananassa) und des Pfirsichs (Prunus persica) (1995)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 78 (1995), S. 847-856 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: On the Biosynthesis of γ-Dodecanolactone in Ripening Fruits: Flavor Constituents from Strawberries (Fragaria ananassa) and Peaches (Prunus persica)Administration of deuterium-labelled 9,10-expoxy[8,8-2H2]heptadecanoic acid 8a/b and 9,10-dihydroxy-[8,8-2H2]methylheptadecanoate 9 as lower analogues of oleic acid 1 to ripening fruits of strawberries (Fragaria ananassa) and peaches (Prunus persica) results in the emission of labelled γ-undecanolactone (5) as the lower analog of γ-dodecanolactone (2). The transformation proceeds with loss of a single D-atom from C(8) of the precursors. Early precursors, like the C17-epoxy-acids 8a/b yield (4R)-γ-undecanolactone (5) of high enantiomeric purity, while later intermediates results in (4R)-γ-undecanolactone (5) of low purity. The data support a biosynthetic sequence involving the consecutive action of an epoxide hydrolase and β-oxidation to generate the correct chain length of the lactone percursor. The final steps proceed via cyclization of the 3,4-dihydroxyundecanoic acid 13 to the 3-hydroxy-γ-undecanolactone 14. Elimination of H2O and reduction of the intermediate γ-undec-2-enolactone 15 terminate the biosynthesis of 5. The sequence is representative for the biosynthesis of naturally occurring γ-dodecanolactone (2).
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19950780406
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  • 5
    Digitale Medien
    Digitale Medien
    Biosynthesis of Dodecano-4-lactone in Ripening Fruits: Crucial Role of an Epoxide-Hydrolase in Enantioselective Generation of Aroma Components of the Nectarine (Prunus persica var. nucipersica) and the Strawberry (Fragaria ananassa) (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1488-1496 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Early steps in the biosynthesis of dedecano-4-lactone in ripening nectarines (Prunus persica var. nucipersica) and strawberries (Fragaria ananassa) were studied using cis-9,10-([18O]epoxy)heptadecanoic acid (5), instead of the natural C18-precursor epoxystearic acid 1. In nectarines, an epoxide hydrolase catalyzed, in a highly regio- and enantioselective reaction, the attack of H2O at C(9) of epoxy acid 5 yielding preferentially (9R,10R)-dihydroxyheptadecanoic acid 6a as an early intermediate and, after further metabolization, undecano-4-lactone 7a. In strawberries, the same transformation exhibited only a moderate regio- and enantioselectivity. Besides the previously established function of phytogenic epoxide hydrolases involved in generating oxygenated fatty-acid derivatives, which are used in cutin monomer production and plant defence, a new rǒle for these enzymes now emerges in the enantioselective production of aroma components of ripening fruits. The cis-9,10-([18O]epoxy)heptadecanoic acid (≥ 98% 18O; 5) was obtained in good overall yield (68%) from isopropyl (9Z)-heptadec-9-enoate using 18O2 gas in a free-radical chain reaction in the presence of 2-methylbutanal.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19960790521
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  • 6
    Digitale Medien
    Digitale Medien
    Synthesis of Enantiomerically Pure Pheromones of South-Pacific Brown Algae: Hormosirene and Dictyopterene ADedicated to Prof. Dr. Karl Dimroth on the occasion of his 75th birthday (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 1186-1192 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Hormosirene ((-)-1; (1R,2R)-1-((1E,3Z)-1,3-hexadienyl)-2-vinylcyclopropane) is the specific sex attractant of several brown algae of the Australian shelf, while dictyopterene A ((+)-2; (1R, 2R)-1-((1E)-1-hexenyl)-2-vinylcyclopropane) is found as a minor constituent of the pheromone bouquets. The asymmetric synthesis of the two hydrocarbons is performed by resolution of the amides (-)-5 and (+)-5a obtained from (-)-(R)-2-phenylglycinol and racemic trans-vinylcyclopropanecarboxylic acid (rac-4) on silica gel. Both diastereoisomers are obtained optically pure. They are converted by stereoselective Wittig olefination into the title compounds. Compound (-)-1 is the active mating pheromone of the reproductive system of the seaweed Xiphophora chondrophylla as established by biological-activity assays.
    Zusätzliches Material: 1 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19850680514
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  • 7
    Digitale Medien
    Digitale Medien
    Enantioselective Syntheses and Absolute Configurations of Viridiene and Aucantene, Two Constitutents of Algae Pheromone BouquetsDedicated to Prof. Dr. F. Lingens on the occasion of his 60th birthday (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 2062-2073 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Viridiene ((+)-6; (+)-(3R,4S)-3-((1Z)-1,3-butadienyl)-4-vinylcyclopentene) and aucantene ((+)-18; (+)-(4R,5R)-4-((1E)-1-propenyl)-5-vinylcyclohexene) are constituents of the pheromone bouquets of several brown algae species. Key synthons to the title compounds are optically active γ-lactones with known or experimentally determined absolute configurations. Horse liver alcohol dehydrogenase, which catalyses the oxidation of meso- and racemic non-meso diols to chiral lactones, and pig-liver esterase, which catalyzes the saponification of meso-diesters to chiral half-esters, were utilized for the asymmetric synthesis of such precursors. The racemic non-meso diol rac-1 is converted to the two stereoisomeric γ-lactones (+)-2 and (+)-3 which are readily separated. meso-Diol 12 is oxidized to the chiral γ-lactone (-)-11. Its enantiomer (+)-11 is obtained by enantioselective saponification of the meso-diester 9 with pig-liver esterase. Appropriately designed syntheses lead from these chiral intermediates to both enantiomers (+)- and (-)-6 of viridiene and (+)- and (-)-18 of aucantene. In addition, kinetically controlled reduction of the racemic aldehydes rac-5a and rac-15 with horse liver alcohol dehydrogenase offers a convenient alternative to the enantioselective preparation of the enantiomers of the two hydrocarbons 6 and 18. Chromatography of 6 on triacetylated cellulose as a stationary chiral phase confirms the enantiospecificity of the synthetic routes designed.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19850680731
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  • 8
    Digitale Medien
    Digitale Medien
    Sterospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae. Part IV.Part III: [28]. (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 1025-1040 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Giffordene (=(2Z,4Z,6E,8Z)-2,4,6,8-undecatetraene; 9f) and five steroisomers are new C11H16 hydrocarbons from the marine brown alga Giffordia mitchellae. Their synthesis is based on non-stereoselective Wittig reactions of (E)-2-alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting (E/Z)-pairs. The uniform enynes (〉98% purity) are then stereospecifically reduced to (Z)-alkenes with Zn(Cu/Ag) in aq. MeOH at r.t. 13C- and 1 H-NMR data of the new tetraenes are presented. Biosynthetically, giffordene (9f) originates from dodeca-3,6,9-trienoic acid via an unstable (3Z,5Z,8Z)-1,3,5,8,-undecatetraene followed by a thermally allowed antarafacial 1,7-sigmatropic hydrogen shift to the (2Z,4Z,6E,8Z)-isomer9f.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19870700415
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  • 9
    Digitale Medien
    Digitale Medien
    Changes in the Leaf Surface Chemistry of Apium graveolens (Apiaceae) stimulated by jasmonic acid and perceived by a specialist insect (1997)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 1408-1420 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Treatment of celery leaves (Apium graveolens, cv. secalinum) with Jasmonic acid (JA, 1) or analogues of amino-acid conjugates of Jasmonic acid such as the leucine conjugate with 1-oxoindan-4-carboxylic acid (IN-ILE, 2) stimulated the biosynthesis of the furanocoumarins psoralen (6), xanthotoxin (8), bergapten (7), and isopimpinellin (9). Besides the increase of the compounds within the leaf, a significant amount (ca. 20%) of the total furanocoumarins was deposited on the surface of the leaf. The two monomethoxy furanocoumarins, 7 and 8, began to increase steadily and simultaneously within the leaf and on the leaf surface ca. 40 h after the onset of the jasmonic-acid stimulus. Within the leaf, the ratio 7/8 was ca. 1.3:1.0, while among the surface lipids 8 dominated (7/8 0.8:1.0), indicating that the export of the compounds to the surface is not a simple diffusive translocation along the oil-ducts. Females of the carrot fly (Diptera, Psilidae) responded with an increased oviposition to the altered leaf surface chemistry of the JA-treated celery plants. The effect shown for total leaves was corroborated by surrogate leaves treated with leaf-surface extracts of JA-induced leaves. Based on the known stimulation of oviposition by furanocoumarins, we conclude that the enhanced amount of furanocoumarins on the surface can explain the insects' preference for the JA-stimulated plants. This is the first report of a JA-induced change of the surface chemistry of a plant and an increase of the acceptability of treated leaves for a specialist insect, like the carrot fly.
    Zusätzliches Material: 5 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19970800507
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  • 10
    Digitale Medien
    Digitale Medien
    Separation of enantiomeric algal pheromones and related hydrocarbons by gas-liquid Chromatography on Modified Cyclodextrins as Chiral Stationary Phases. Biosynthetic relevance of racemic by-products (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 1288-1292 
    Details
    ISSN: 0018-019X
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The separation of the enantiomers of the olefinic hydrocarbons multifidene 3 and aucantene 5 from the pheromone blend of the two seaweeds Cutleria multifida and Chorda tomentosa is achieved by gas chromatography on modified cyclodextrins as chiral stationary phases. The method is also applicable for the separation of enantiomeric alkyl-, alkenyl- or alkynyl-substituted cyclooctadienes and cyclopentenes. A plausible rational is presented for the biosynthesis of racemic by-products of algal pheromone blends.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/hlca.19890720616
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