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  • 1
    Electronic Resource
    Electronic Resource
    Preparation and isolation of 2-methylamino-3-phenylpropanoic acid enantiomers using selective crystallization (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 386-389 
    Details
    ISSN: 0899-0042
    Keywords: optical resolution ; diastereomeric method ; molecular compound ; 2-chloro-3-phenylpropanoic acid ; 2-methylamino-3-phenylpropanoic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: First, (RS)-2-chloro-3-phenylpropanoic acid [(RS)-CPP] was optically resolved using ethyl (S)-phenylalaninate as a resolving agent, aiming at preparation of optically active 2-methylamino-3-phenylpropanoic acid (MPP). The (R)-CPP obtained as the sodium salt monohydrate was reacted with methylamine to give (S)-2-methylamino-3-phenylpropanoic acid [(S)-MPP]. Next, the optical resolution of (RS)-MPP was also attempted via molecular compound formation with optically active mandelic acid (MAN). The molecular compound of (R)-MPP with (S)-MAN [(R)-MPP (S)-MAN] was obtained as the less soluble diastereomeric compound, while the (S)-MPP (S)-MAN compound was found to be the more soluble one. Recrystallization of (R)-MPP (S)-MAN compound from water, followed by treatment with acetone, gave optically pure (R)-MPP in 79% yield, based on a half amount of the starting (RS)-MPP. The (S)-MPP obtained from (S)-MPP (S)-MAN compound was again subjected to formation of molecular compound with (R)-MAN to give optically pure (S,)-MPP in 66% yield. Chirality 9:386-389, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Biologically active glycosides from asteroidea, XIII. Glycosphingolipids from the starfish Acanthaster planci, 2. Isolation and structure of six new cerebrosides (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 19-24 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Biologisch aktive Glycoside aus Asteroidea, XIII. - Glycosphingolipide aus dem Seestern Acanthaster planci, 22). - Isolierung und Struktur von sechs neuen CerebrosidenSechs neue Cerebroside (Ceramid-monohexoside), Acanthacerebrosid A (1), B (2), C (3), D (4), E (5) und F (6), wurden aus der wasserunlöslichen Lipid-Fraktion des Chloroform-Methanol-Extrakts des Seesterns Acanthaster planci isoliert. Auf Grund der chemischen und spektrometrischen Untersuchungen ließen sich die Strukturen als 1-O-(β-D-Glucopyranosyl)-substituiertes (2S,3S,4R)-2-[(2R)-2-Hydroxytetracosanoylamino]-1,3,4-hexadecanetriol (1), (2S,3S,4R)-2-[(2R)-2-Hydroxyhexadecanoylamino]-1,3,4-docosantriol (2), (2S,3S,4R,13E)-2-[(2R)-2-Hydroxyhexadecanoylamino]-13-docosen-1,3,4-triol (3), (2S,3R,4E,10E)-2-[(2R)-2-Hydroxydocosanoylamino]-4,10-octadecadien-1,3-diol (4), (2S,3R,4E,10E)-2-[(2R)-2-Hydroxytricosanoylamino]-4,10-octadecadien-1,3-diol (5) und (2S,3R,4E,10E)-2-[(2R)-2-Hydroxytetracosanoylamino]-4,10-octadecadien-1,3-diol (6) charakterisieren. Die Isolierung der strukturell sehr ähnlichen Cerebroside gelang durch Reversed-Phase-HPLC. Negativ-FABMS-Spektrometrie ließ sich erfolgreich zur Molmassen-Bestimmung der Cerebroside einsetzen.
    Notes: Six new cerebrosides (ceramide monohexosides), acanthacerebroside A (1), B (2), C (3), D (4), E (5), and F (6) were isolated from the water-insoluble lipid fraction of the chloroform-methanol extract of the starfish Acanthaster planci. On the basis of chemical and spectral evidences, they were characterized as 1-O-(β-D-glucopyranosyl)-substituted (1S,3S,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol (1), (2S,3S,4R)-2-[(2R)-2-hydroxyhexadecanoylamino]-1,3,4-docosanetriol (2), (2S,3S,4R,13E)-2-[(2R)-2-hydroxyhexadecanoylamino]-13-docosene-1,3,4-triol (3), (2S,3R,4E,10E)-2-[(2R)-2-hydroxydocosanoylamino]-4,10-octadecadiene-1,3-diol (4), (2S,3R,4E,10E)-2-[(2R)-2-hydroxydocosanoylamino]-4,10-octadecadiene-1,3-diol (5), and (2S,3R,4E,10E)-2-[(2R)-2-hydroxytetracosanoylamino]-4,10-octadecadiene-1,3-diol (6). Reversed-phase HPLC was effective to isolate these cerebrosides revealing the very close resemblance in structure. Negative FABMS spectrometry was useful in providing information on the molecular mass of the cerebrosides.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880105
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  • 3
    Electronic Resource
    Electronic Resource
    Pheromone synthesis, CIV. Synthesis of the enantiomers of α-Phellandren-8-ol (p-mentha-1,5-dien-8-ol), a monoterpene from bark beetles (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 93-95 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomerically pure (R)-α-phellandren-8-ol (p-mentha-1,5-dien-8-ol, 1a) was synthesized from (R)-carvone (2). Similarly (S)-1 a was synthesized from (S)-2.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880116
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  • 4
    Electronic Resource
    Electronic Resource
    Biologically active glycosides from asteroidea, XVII. Glycosphingolipids from the starfish Acanthaster planci, 3. Isolation and structure of two new ceramide lactosides (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 1181-1183 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Biologisch aktive Glycoside aus Asteroidea, XVII. - Glycosphingolipide aus dem Seestern Acanthaster planci, 3. - Isolierung und Struktur von zwei neuen Ceramid-LactosidenAus der wasserlöslichen Lipid-Fraktion des Chloroform/Methanol-Extraktes des Seesterns Acanthaster planci ließen sich zwei neue Acanthalactoside A (1) und B (2) isolieren. Aufgrund chemischer und spektroskopischer Befunde wurden die Strukturen von 1 und 2 als 1-O-[β-D-Galactopyranosyl-(1→4)-β-D-glucopyranosyl]-substituiertes (2S,3S,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol (1) und (2S,3S,4R,13E)-2-[(2R)-2-hydroxyhexadecanoylamino]-13-docosen-1,3,4-triol (2) ermittelt. Die Isolierung des Glycosphingolipid-Gemisches aus der wasserlöslichen Lipid-Fraktion, die auch anderes Material wie zum Beispiel Steroid-Saponine enthalten, gelang mit Hilfe der Reversed-phase-Säulenchromatographie. Reversed-phase-HPLC ließ sich effektiv zur Isolierung der strukturell sehr ähnlichen Ceramiddihexodside einsetzen. Negativ-FAB-Massenspektrometrie diente zur erfolgreichen Bestimmung und Absicherung der Struktur der Ceramid-dihexoside.
    Notes: Two new ceramide lactosides, acanthalactoside A (1) and B (2) were isolated from the water-soluble lipid fraction of the chloroform/methanol extract of the starfish Acanthaster planci. On the basis of chemical and spectral evidence, the structures of 1 and 2 were characterized as 1-O-[β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]-substituted (2S,3S,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol (1) and (2S,3S,4R,13E)-2-[(2R)-2- hydroxyhexadecanoylamino]-13-docosene-1,3,4-triol (2), respectively. Reversed-phase column chromatography was useful to obtain the glycosphingolipid mixture from the watersoluble lipid fraction containing also other material such as steroid saponins. Reversed-phase HPLC was also effectual to isolate these ceramide dihexosides reveling very close resemblance in structure. Negative FAB mass spectrometry was successfully used for the determination and confirmation of the ceramide dihexosides.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819881213
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  • 5
    Electronic Resource
    Electronic Resource
    Pheromone synthesis, CIX. Synthesis of the four stereoisomers of 6,12-dimethyl-2-pentadecanone, the sex pheromone of Diabrotica balteata LeConte (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 717-720 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Pheromonsynthesen, CIX.  -  Synthese aller vier Stereoisomeren von 6,12-Dimethyl-2-pentadecanon, dem Sexualpheromon von Diabrotica balteata LeConteEs wird die Synthese der vier Stereoisomeren des 6,12-Dimethyl-2-pentadecanons (1), dem Sexualpheromon des Gurkenkäfers Diabrotica balteata LeConte, aus den Enantiomeren von Citronellol (2) beschrieben.
    Notes: The synthesis of the four stereoisomers of 6,12-dimethyl-2-pentadecanone (1), the sex pheromone of the banded cucumber beetle (Diabrotica balteata LeConte), was achieved employing the enantiomers of citronellol (2) as the starting materials.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880715
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  • 6
    Electronic Resource
    Electronic Resource
    Triphenylstibine oxide-phosphorus(V) sulfide as a novel condensation catalyst system: application to the synthesis of dipeptides (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 3 (1989), S. 355-357 
    Details
    ISSN: 0268-2605
    Keywords: Triphenylstibine oxide ; phosphorus pentasulfide ; catalytic peptide synthesis ; amidation ; thiocarboxylic acids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Triphenylstibine oxide (Ph3SbO) and phosphorus(V) sulfide (P4S10) synergistically catalyzed the aminolysis of N-protected amino-acids with amino-acid esters in benzene. Ph3SbO accelerated both the initial conversion of carboxylic moieties into the corresponding thiocarboxylic moieties by P4S10 and the subsequent aminolysis of the resulting thiocarboxylic acids. Thus, dipeptides such as Z-A-A′-OEt (where Z = PhCH2OC(O)- and A,A′ = Ala,Gly; Gly,Gly; Leu,Gly; Phe,Gly; Phe,Leu;Ser,Gly; Val,Gly, respectively) were conveniently prepared even at 35°C.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/aoc.590030410
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  • 7
    Electronic Resource
    Electronic Resource
    Biologically active glycosides from asteroidea, XIX. Glycosphingolipids from the starfish Acanthaster planci 4. Isolation and structure of five new gangliosides (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 43-50 
    Details
    ISSN: 0170-2041
    Keywords: Glycosphingolipids ; Gangliosides ; Acanthagangliosides ; Starfishes ; Acanthaster planci ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Five new gangliosides  -  acanthaganglioside A (1), B (2), C (3), D (4) and E (5)  -  were purified from the water-soluble lipid fraction of the chloroform/methanol extract of the starfish Acanthaster planci. Based on chemical and spectroscopic data, the structures of 1-5 were elucidated. The gangliosides consist of one homogeneous long-chain base, five or six sugars and different fatty acids. Reversed-phase HPLC using methanol/ammonia/water as solvent was effective in isolating these gangliosides, showing the very close similarity in their structures. Negative FAB mass spectrometry provided important information both on the structure of the sugar moiety and on the molecular mass of the gangliosides. Partial hydrolysis by hot pyridine/water or hot water was useful for structure elucidation of the complex oligosaccharide moieties.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199019900107
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  • 8
    Electronic Resource
    Electronic Resource
    Electron spin resonance study on radicals stabilized by the σ-π captodative effect1 (1988)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 1 (1988), S. 197-207 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: ESR spectra of l-cyano-2-(trimethylsilyl)ethyl and related radicals were recorded. Temperature dependent ESR spectra of these radicals revealed that electron-releasing trimethylsilylmethyl and electron-withdrawing cyano groups synergetically functioned to stabilize the radical centers due to σ-π captodative effects.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610010404
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  • 9
    Electronic Resource
    Electronic Resource
    Structural studies of halogen adducts of some cyclic selenides and tellurides by 1H, 13C, 77Se and 125Te NMR. Evidence for the formation of molecular complexes of selenoxanthone and selenanthrene with bromineFor a preliminary contribution, see Ref. 1. (1990)
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 3 (1990), S. 369-374 
    Details
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: 1H, 13C, 77Se and 125Te NMR spectra were recorded for selenoxanthone (1a), telluroxanthone (2a), selenanthrene (3a), related compounds and their halogen adducts to elucidate the structure of the adducts in solutions. Although selenides react with bromine to give trigonal bipyramidal (TB) hypervalent complexes in general, 1a reacted with bromine to yield a molecular complex (MC). Its chlorine adduct was found to be a TB. The effective electronegativity of selenium in 1a may be modulated by conjugation with the strongly electron-withdrawing carbonyl group. In the case of 2a, its halogen adducts were TBs. The structure of the bromine adduct of 3a was also demonstrated to be an MC from NMR data.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/poc.610030604
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  • 10
    Electronic Resource
    Electronic Resource
    Studies on Metabolites of Mycoparasitic Fungi, 6. 15-Hydroxyacorenone: New Acorane-Type Sesquiterpene from the Culture Broth of the Mycoparasitic Fungus Trichoderma harzianum (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2579-2580 
    Details
    ISSN: 0947-3440
    Keywords: 15-Hydroxyacorenone ; Acorane-type sesquiterpene ; 13C NMR ; Trichoderma harzianum ; Mycoparasitic fungus ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new acorane-type sesquiterpene, 15-hydroxyacorenone, has been isolated from the culture broth of Trichoderma harzianum, which in turn was isolated from the fruiting body of a medicinal mushroom, Ganoderma lucidum (Fr.) Karst. (the oriental crude drug “Lin-Chi”). The structure of 15-hydroxy-acorenone was determined by spectroscopic methods to be (1S,4S,5S)-8-hydroxymethyl-1-isopropyl-4-methylspiro[4.5]-dec-8-en-7-one (1).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971224
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