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  • Articles  (24)
  • Organic Chemistry  (13)
  • Biochemistry and Biotechnology  (7)
  • Humans  (4)
  • 1990-1994  (24)
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  • Articles  (24)
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  • 1
    Electronic Resource
    Electronic Resource
    The kinetics of diastereomeric amino acids with o-phthaldialdehyde (1991)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 3 (1991), S. 471-475 
    Details
    ISSN: 0899-0042
    Keywords: amino acids ; kinetics ; epimers ; OPA ; postcolumn reaction detection ; fluorescence detection ; amino acid racemization ; dating methods ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The kinetics of the reaction of the amino acid epimers L-isoleucine, D-alloisoleucine, L-threonine, and D-allo-threonine with o-phthaldialdehyde and mercaptoethanol were determined at 25°C. L-Isoleucine reacts faster than its D-epimer whereas L-threonine reacts slightly slower than its D-epimer. In the case of isoleucine, the consequence can be an allo/iso ratio which in the worst case is 25% too low if these amino acids are quantified by liquid chromatography and o-phthaldialdehyde fluorescence detection. The effect on dating of fossils by amino acid racemization is discussed.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530030611
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  • 2
    Electronic Resource
    Electronic Resource
    Syntheses and X-Ray Structures for Model Compounds of a Pyrimidinediyl-Based Rigid-Rod Aromatic Polyamide (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 184-189 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A variety of model compounds for the pyrimidinediyl-based rigid-rod polyamide poly[imino-(pyrimidine-2,5-diyl)-imino-tetraphthaloyl] (PPYMT) was prepared, in order to compare their conformations to several model compounds of the related, fully aromatic polymer poly(p-phenyleneterephthalamide) (PPTA). In particular, the structures of N-(2-pyrimidyl)benzamide (PYMB) and its complexed form bis[(N-pyrimidin-2-yl)benzamide]nickel(II) dichloride (NiPYMB) were determined by X-ray diffraction. The molecular packing in these crystals provides us with a model for the possible ‘cross-linking’ of PPYMT fibers. The structures of the trimer model compounds N,N′ -bis(2-pyrimidyl)terephthalamide (PYTA) and N,N′ -bis(benzoyl)-2,5-diaminopyrimidine (BDAP) yield information about the conformation of PPYMT chains and are compared to analogous model compounds of PPTA.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750116
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 1848-1865 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Eight (Z)-isomers of lycopene were prepared by stereocontrolled syntheses and fully characterized by 1H-NMR, 13C-NMR, mass, and UV/VIS spectroscopy: (5Z)-, (7Z)-, (15Z)-, (5Z,5′Z)-, (7Z,7′Z)-, (7Z,9Z)-, (9Z,9′Z)-, and (7Z,9Z,7′Z,9′Z)-lycopene. Six additional (Z)-isomers, namely (9Z)-, (13Z)-, (5Z,9′Z)-, (9Z,13′Z)-, (5Z,9Z,5′Z)-, and (5Z,13Z,5′Z)-lycopene, were isolated in small quantities from isomer mixtures by semiprep. HPLC and were identified by 1H-NMR spectroscopy.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750611
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  • 4
    Electronic Resource
    Electronic Resource
    Incapability of Gluconobacter oxydans to produce tartaric acid (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Biotechnology and Bioengineering 40 (1992), S. 183-186 
    Details
    ISSN: 0006-3592
    Keywords: Gluconobacter oxydans ; 5-ketogluconic acid ; tartatic acid ; vanadate ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: The dependence of tartaric acid production by Gluconobacter oxydans ssp. oxydans ATCC 19357 and G. oxydans ssp. suboxydans ATCC 621 on vanadate was investigated. It was found with both organisms that trataric acid could only be produced in a medium containing vanadate (NH4VO3). A proposed intermediate of the tartaric acid metabolism in G. oxydans, 5-ketogluconic acid, was tested on its reactivity in the presence of the oxidizing catalyst vanadate. It could be shown that 5-ketogluconic acid and the catalyst vanadate, but not the activity of G. oxydans, were responsible for the formation of tartaric acid. G. oxydans was not able to produce tartaric acid by itself. The stereochemical identity of the formed tartaric acid could be identified as the L-(+)-type. Oxalic acid was formed from 5-ketogluconic acid with vanadate in the absence and in the presence of G. oxydans. The ratio of oxalic acid to tartaric acid was 1:1.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bit.260400126
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  • 5
    Electronic Resource
    Electronic Resource
    Chemostat cultivation of Candida blankii on sugar cane bagasse hemicellulose hydrolysate (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Biotechnology and Bioengineering 40 (1992), S. 353-358 
    Details
    ISSN: 0006-3592
    Keywords: Bagasse hemicellulose hydrolysate ; chemostat ; Candida blankii ; D-xylose ; single cell protein ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: A Candida blankii yeast isolate was grown in sugar cane bagasse hemicellulose hydrolysate at 38°C in carbon-limited chemostat culture. The pretreatment of the acid hydrolysate prior to microbial cultivation consisted of partial neutralization with ammonia and sodium hydroxide, plus the addition of phosphorus, which was the only other growth-limiting nutrient apart from nitrogen. The cell yield coefficient on nitrogen was 16.78. The critical dilution rate was higher (0.35 h-1) in diluted hydrolysate than in undiluted hydrolysate (0.21 h-1). In undiluted hydrolysate at a dilution rate of 0.1 h-1 and pH 4, where aseptic procedures proved unnecessary, the cell and protein yield coefficients were 0.53 and 0.26, respectively, and no residual carbon substrates (D-xylose, L-arabinose, D-glucose, and acetic acid) were detected. The cell yield on oxygen increased linearly as a function of dilution rate. The cellular content of protein, carbohydrate, and RNA also increased with an increase in dilution rate, whereas the DNA content decreased slightly. C. blankii has considerable potential for the production of single cell protein from hemicellulose hydrolysate, because of its ability to utilize all of the major carbon substrates in the hydrolysate at a low pH and at a relatively high temperature with a high protein yield. © 1992 John Wiley & Sons, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bit.260400304
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  • 6
    Electronic Resource
    Electronic Resource
    Enzymatic resolution of racemic amines in a continuous reactor in organic solvents (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Biotechnology and Bioengineering 40 (1992), S. 760-767 
    Details
    ISSN: 0006-3592
    Keywords: (R)-1-(1-naphthyl)ethylamine ; (R)-1-aminoindan ; subtilisin ; organic solvent ; stereoselective aminolysis ; immobilized enzyme ; continuous process ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: An enzymatic process has been developed for the continuous production of the pharmaceutically important intermediate (R)-1-aminoindan and of the chiral resolving agent (R)-1-(1-naphthyl)ethylamine. The process consists of the subtilisin catalyzed stereoselective aminolysis of the racemic primary amine with an active ester in organic solvent. The competing nonenzymatic reaction has been suppressed by appropriate choice of solvent and reactant's concentration and by minimizing the time of contact between the amine and the active ester. Subtilisin was immobilized on glass beads and the reaction carried out in a continuous-flow column bioreactor. By using a 450-mL column bioreactor containing 5.7 g of subtilisin immobilized on 570 g of glass beads, 1.6 kg of racemic 1-(1-naphthyl)ethylamine was resolved after 320 h of continuous operation with only a slight loss of the enzymatic activity. During the whole process, the optical purity of the chiral amine eluting from the column was higher than 90%. A facile procedure was developed for separating the unreacted (R)-amine from the (S)-amide and for the recycling of the solvent 3-methyl-3-pentanol and the active ester 2,2,2-trifluoroethyl butyrate. © 1992 John Wiley & Sons, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/bit.260400703
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  • 7
    Electronic Resource
    Electronic Resource
    A vivid model illustrating chiral recognition induced by achiral structures (1990)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 2 (1990), S. 208-210 
    Details
    ISSN: 0899-0042
    Keywords: enantioselectivity ; three-point model ; didactic model ; chiral separations ; ligand-exchange chromatography ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: If diastereomeric complexes are adsorbed on a surface or if they include a molecule of solvent, two points of attractive interaction between the chiral species of the complex can be sufficient for mutual chiral recognition of these species. In special cases even one single point of interaction is sufficient. This extension of the three-point contact rule of Dalgliesh, first observed in chiral ligand-exchange chromatogrphy, can be demonstrated by using hands.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530020403
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  • 8
    Electronic Resource
    Electronic Resource
    (Z)-1,1-dichloro-2-(4-benzyloxyphenyl)-2,3-bis(4-methoxyphenyl)cyclopropane: The synthesis and enantiomeric separation of an antitumor agent (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 41-45 
    Details
    ISSN: 0899-0042
    Keywords: chiral HPLC ; Chiralpak AD ; amylose carbamate stationary phase ; antiestrogen ; breast cancer ; dichlorotriarylcyclopropane ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (Z)-1,1-Dichloro-2-(4-benzyloxyphenyl)-2,3-bis(4-methoxyphenyl)cyclopropane (5), a potential antitumor agent designed to treat breast cancer, was prepared in three steps. A stereospecific palladium-catalyzed cross coupling reaction which provided the intermediate (Z)-triaryl alkene 4 was a crucial step in the synthesis. Makosza phase transfer reaction on 4 gave the enantiomeric (Z)-dichlorocyclopropane derivatives 5 which were resolved by semipreparative HPLC on a chiral stationary phase consisting of amylose tris-3,5-dimethylphenyl carbamate coated on silica gel. © 1994 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060108
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  • 9
    Electronic Resource
    Electronic Resource
    Reversed-Phase LC resolutions of chiral antiarrhythmic agents via derivatization with homochiral isothiocyanates (1990)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 2 (1990), S. 43-51 
    Details
    ISSN: 0899-0042
    Keywords: mexiletine ; flecainide ; tocainide ; propafenone ; chirality ; enantiomers ; HPLC ; homochiral derivatization ; isothiocyanates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The search for new antiarrhythmic agents has been intense, because the established drugs for the treatment of cardiac arrhythmias are neither uniformly effective nor well-tolerated. Among the recently introduced new anti-arrhythmic agents are tocainide (TOC), mexiletine (MEX), flecainide (FLE), and propafenone (PRO). Each of these drugs is a chiral amine used clinically as the racemic mixture. We have examined the high-performance liquid chromatographic chiral resolution of the above four drugs via derivatization with homochiral derivatizing agents (HDAs). The amino functionality of the drugs was reacted with four homochiral isothiocyanates, 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (TAGIT), (R)-α-methylbenzyl isothiocyanate (RAMBI), (S)-1-(1-naphthyl)ethyl isothiocyanate (SNEIT), and (R)-1-(2-naphthyl)ethyl isothiocyanate (RBEIT). Complete separation of the two peaks (resolution factor R = 1.5) was achieved with all four HDAs for TOC, with TAGIT, RBEIT, and RAMBI for MEX, with TAGIT and SNEIT for PRO, and only with TAGIT for FLE. SNEIT was used to develop analytical procedures for the determination of the enantiomeric composition of TOC in human urine and blood serum. The four HDAs offer several advantages over many other HDAs and should be useful in studies of enantioselective drug action and disposition.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530020107
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  • 10
    Electronic Resource
    Electronic Resource
    Structure elucidation of a Pyoverdin Produced by Pseudomonas aeruginosa ATCC 27 853 (1993)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 335 (1993), S. 83-87 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The primary structure of a pyoverdin (Pa TII) isolated from an iron deficient culture medium of Pseudomonas aeruginosa ATCC 27 853 has been elucidated by spectroscopic methods and degradation studies. Total assignment of 1H and 13C resonances as well as sequential information were achieved by two-dimensional NMR techniques: HOHAHA1, NOESY, HSQC and HMBC. The structure consists of the common pyoverdin chromophore 5-amino-2,3-dihydro-8,9-dihydroxy-1H-pyrimido [1,2-a]quinoline-1-carboxylic acid with succinic acid bound amidically to its amino group and the carboxyl group linked to the N-terminus of D-Ser-D(CHO) OHOrn-L-Orn-Gly-D-aThr-L-Ser-L-cOHOrn. According to the short-hand nomenclature suggested in [2, 3] the pyoverdin may be described as pyoverdin-Q-so′ OGtaSo′*-SUC.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19933350113
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