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  • 1
    Electronic Resource
    Electronic Resource
    Characteristics of l-alanine transport in cardiac sarcolemmal vesicles and into isolated cardiac myocytes (1998)
    Springer
    Pflügers Archiv 436 (1998), S. 384-390 
    Details
    ISSN: 1432-2013
    Keywords: Key words l-Alanine ; l-Glutamate ; Transport ; Sarcolemma ; Myocardial protection ; Heart cells
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract  During cardiac insults, heart cells synthesise and accumulate alanine as a part of the anaerobic energy production pathway. The transport of alanine presumably influences this pathway, making it important to characterise the l-alanine transporter in the heart. In this study, we have investigated the transport of l-alanine across the sarcolemma using a novel approach, namely utilisation of two preparations: cardiac sarcolemmal vesicles and cardiac myocytes. Both preparations were isolated from the heart of the same mammalian species. l-Alanine uptake in both preparations was sodium dependent. In the sarcolemmal vesicles, the sodium dependent component was electrogenic and saturated with an estimated Michaelis-Menten constant (K m) and maximal reaction velocity (V max) of 0.48±0.18 mM and 279.97±64.17 pmol/mg per min respectively at room temperature. In the isolated myocytes, l-alanine uptake was linear in sodium-containing media, with an estimated K m and V max of 9.65±0.76 mM and 169.81±13.22 pmol/µl per min respectively at 10°C for the sodium-dependent component. Inhibition of cotransport by a variety of substrates indicated that l-alanine uptake in the heart is mediated by an A- or ASC-like system. These characteristics of l-alanine transport suggest that under ischaemic conditions, l-alanine efflux will be activated, thus allowing for the continuous utilisation of other amino acids for energy production.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004240050647
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  • 2
    Electronic Resource
    Electronic Resource
    Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone A Analogues by the Olefin Metathesis Approach (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1957-1970 
    Details
    ISSN: 0947-6539
    Keywords: epothilone ; oxazoles ; cyclopropanes ; metathesis ; total synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: For structure-activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem-dimethyl group at position C-4 (4,4-ethano-epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7-9 for the oxazole series (compounds 2, 14-18, 21-26) and building blocks 8, 30, and 31 for the 4,4-ethano series (compounds 3,39-43, 46-51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)-(PCy3)2], and d) epoxidation of the macrocycle double bond.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970031211
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  • 3
    Electronic Resource
    Electronic Resource
    Total Synthesis of Oxazole- and Cyclopropane-Containing Epothilone B Analogues by the Macrolactonization Approach (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1971-1986 
    Details
    ISSN: 0947-6539
    Keywords: epothilone ; oxazoles ; cyclopropanes ; total synthesis ; macrolactonizations ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In order to probe structure-activity relationships in the epothilone area, two series of epothilone B analogues have been designed and synthesized. The first series containing an oxazole moiety in place of a thiazole on the side chain was constructed by utilizing key intermediates 7-9 or 10, 12, and 13 (Scheme 1), whereas the second series containing an ethano group instead of the gem-dimethyl group at position 4 was synthesized from fragments 42 and 43. A Yamaguchi-type macrolactonization reaction was used to construct the macrocycle from a secoacid, which was assembled, in both cases, by means of a) an aldol reaction, b) an Enders alkylation, and c) a Wittig-type reaction. This convergent strategy provided access to oxazole analogues 2,4,29-32 and 4,4-ethano derivatives 3,40,60-63 for biological studies.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970031212
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