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  • 1
    Electronic Resource
    Electronic Resource
    Change of reactivity of lysine residues upon actin polymerization (1981)
    s.l. : American Chemical Society
    Biochemistry 20 (1981), S. 5914-5919 
    Details
    ISSN: 1520-4995
    Source: ACS Legacy Archives
    Topics: Biology , Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/bi00523a040
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  • 2
    Electronic Resource
    Electronic Resource
    Comments on the putative stereoselectivity in cysteine-aldehyde reactions. Selective C(2) inversion and C(4) epimerization in thiazolidine-4-carboxylic acids (1979)
    s.l. : American Chemical Society
    Journal of the American Chemical Society 101 (1979), S. 427-432 
    Details
    ISSN: 1520-5126
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ja00496a026
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  • 3
    Electronic Resource
    Electronic Resource
    Oxazepines and thiazepines. XIX Synthesis of optically active 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones (1988)
    Springer
    Monatshefte für Chemie 119 (1988), S. 933-944 
    Details
    ISSN: 1434-4475
    Keywords: Resolution ; Optical purity ; Optically active benzothiazepines
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Optisch aktive 2,3-Dihydro-1,5-benzothiazepin-4(5H)-one (14–17) wurden mittels Racematspaltung und weiterer chemischer Umsetzungen der Nitrocarbonsäuren6–9 hergestellt. Ausgehend von optisch aktiven Carbonsäuren wurden außerdem verschiedene optisch aktive Verbindungen synthetisiert. Die optische Reinheit wurde mit Hilfe der NMR-Spektroskopie überprüft.
    Notes: Abstract Optically active 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones (14–17) have been synthesizedvia resolution and chemical transformation of nitrocarboxylic acids6–9. Starting from the latter various optically active substances have been synthesized as well. Optical purity was checked by NMR spectroscopy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00810103
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  • 4
    Electronic Resource
    Electronic Resource
    Oxidation of o-Methoxyphenols with a Hypervalent Iodine Reagent: Improved Synthesis of Asatone and Demethoxyasatone (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2579-2581 
    Details
    ISSN: 1434-193X
    Keywords: Hypervalent iodine ; Phenols ; Oxidation ; Cyclohexa-2,4-dienones ; Dimerization ; Asatone ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidation of the 2-methoxyphenols 1c-f with phenyliodonium(III) diacetate (PIDA) in methanol resulted in the formation of the cyclohexa-2,4-dienones 4c-f, which dimerized spontaneously to a single product (5c-f) in each case. Using this method the synthesis of asatone (5a) and its demethoxy analogue (5b) was also accomplished starting from the readily available phenol derivatives 1a and 1b, respectively.
    Additional Material: 1 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    Heterocyclische Verbindungen aus Zuckern, XI. Ringschlußreaktion von D-Penicillamin mit 2,3,4,5-Tetra-O-acetyl-aldehyde-L-arabinose; 13C-NMR-Spektren von 2-Poly-acetoxyalkylthiazolidin-4-carbonsäurederivaten (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 701-707 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic Compounds from Sugars, XI1). - Cyclisation of D-Penicillamine with 2,3,4,5-Tetra-O-acetyl-aldehydo-L-arabinose; “C-NMR Spectra of 2-Polyacetoxyalkylthiazolidine-4-carboxylic Acid Derivatives5,5-Dimethyl-2(S)- und 5,5-dimethyl-2(R)-(L-arabino-1',2',3',4' -tetraacetoxybutyl)thiazolidine-4-(S)-carboxylic acids (3 and 4) were obtained by condensation of D-penicillamine (1) with 2,3,4,5-tetra-O-acetyl-aldehydo-L-arabinose (2). The structures of 3 and 4 were ascertained using chemical reactions and 1H-NMR spectroscopy. 13C chemical shift data for the methyl esters (5 and 6) of 3 and 4, for the N-acetyl derivatives (11 and 13) of 5 and 6 and of other 2-polyacetoxyalkylthiazo-lidine-4-carboxylic acids are reported.
    Notes: Die Kondensation von D-Penicillamin (1) mit 2,3,4,5-Tetra-O-acetyl-aldehydo-L-arabinose (2) er-gibt 5,5-Dimethyl-2(S)- und 5,5-Dimethyl-2(R)-(L-arabino-1',2',3',4' -tetraacetoxybutyl)thiazolidine-4(S)-carbonsäure (3 bzw. 4), deren Strukturen auf chemischem Wege und durch 1H-NMR-Spektroskopie bewiesen werden. Die 13C-NMR-Spektren der Methylester (5 bzw. 6) von 3 und 4, der N-Acetylderivate (11 bzw. 13) von 5 und 6 sowie bereits beschriebener 2-Polyacetoxyalkyl-thiazolidin-4-carbonsäuren werden mitgeteilt.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790513
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  • 6
    Electronic Resource
    Electronic Resource
    Darstellung und Konformation der 1,2-cis-Pentopyranosylazide (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1393-1397 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Conformation of 1,2-cis-Pentopyranosyl AzidesReaction of acetylated 1,2-trans-pentopyranosyl halides 1a, b, 2, 3 with NaN3 in HMPT under mild condition yielded all the four 1,2-cis-2,3,4-tri-O-acetylpentopyranosyl azides 4, 6, 8, and 14 which, on deacetylation, gave the free azides 5, 7, 9, and 15. Solution conformations, based on vicinal proton-proton coupling constants, are discussed in terms of 4C1(D)⇌1C4(D) equilibria and comparisons are made with other pyranose derivatives.
    Notes: Die Umsetzung der acetylierten 1,2-trans-Pentopyranosylhalogenide 1a, b, 2, 3 mit NaN3 in HMPT unter milden Bedingungen ergibt die 4 möglichen 1,2-cis-2,3,4-Tri-O-acetylpentopyranosylazide 4, 6, 8 und 14, die durch Entacetylierung in die freien Azide 5, 7, 9 und 15 übergeführt werden. Anhand der vicinalen Proton-Proton-Kopplungskonstanten werden die 4C1(D)⇌1C4(D)-Konformationsgleichgewichte in Lösung diskutiert und mit verwandten Pyranosederivaten verglichen.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860810
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  • 7
    Electronic Resource
    Electronic Resource
    Einfache Synthesen der anomeren, an C-6 modifizierten Galacto- und Glucopyranosylazide (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 235-241 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Facile Syntheses of Galacto- and Glucopyranosyl Azides Substituted at C-6Acetylated 6-chloro-, 6-bromo-, 6-iodo-, and 6-azido-6-deoxy-α-D-glucopyranosyl azides (26, 22, 17, 30), -β-D-glucopyranosyl azides (27, 23, 18, 31), -α-D-galactopyranosyl azides (29, 25, 20, 32), and -β-D-galactopyranosyl azides (29, 25, 20, 33) have been obtained by nucleophilic displacement reactions of the appropriate 6-O-(p-toluenesulfonates) 9-12. Hydrogen iodide elimimation from the 6-iodo-6-deoxyglycosyl azides 17-20 by DBU or DBN leads to the hex-5-enopyranosyl azides with α-D-xylo (43), β-D-xylo (44), α-L-arabino (46), and β-L-arabino configuration. The structures, anomeric configurations, and conformations of the products were determined by 1H-NMR spectroscopy.
    Notes: Acetylierte 6-Chlor-, 6-Brom-, 6-Iod- und 6-Azido-6-desoxy-Derivate des α-D-Glucopyranosylazids (26, 22, 17, 30) und β-D-Glucopyranosylazids (27, 23, 18, 31) sowie des α-D-Galactopyranosylazids (28, 24, 19, 32) und β-D-Galactopyranosylazids (29, 25, 20, 33) wurden durch nucleophile Substitutionsreaktionen der entsprechenden 6-O-(p-Toluolsulfonate) 9-12 gewonnen. Die Dehdroiodierung der 6-Iod-6-desoxyazide 17-20 mit DBU oder DBN führte zu den Hex-5-enopyranosylaziden mit α-D-xylo- (43) und β-D-xylo- (44), sowie α-L-arabino- (46) und β-L-arabino-Konfiguration (45). Die Strukturen, die anomeren Konfigurationen und die Konformationen der Produkte werden durch 1H-NMR-Spektroskopie bestimmt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870314
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  • 8
    Electronic Resource
    Electronic Resource
    Darstellung und 1H-NMR-spektroskopische Untersuchung anomerer 6-Desoxyhexopyranosylazide (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 103-112 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation and 1H NMR Study of Anomeric 6-Deoxyhexopyranosyl AzidesThe preparation of the anomeric forms of L-rhamnopyranosyl azide (3, 12) and of 6-deoxy-L-talopyranosyl azide (8, 18) as well as of β-L-fucopyranosyl azide (21) is described. 1H NMR data unequivocally establish that 3, 12, 18 and 22, and their acetates 2, 11, 19, and 21 exist practically exclusively in the 1C4(L) conformation in D2O and CDCl3 solutions, respectively. Fusing of a 2,2-dimethyl-1,3-dioxolane ring to the hexopyranose brings about a distortion of the latter towards a flattened chair conformation. The chemical shifts of 1-H and 2-H are shown to be of diagnostic value in assessing the anomeric configurations of title compounds.
    Notes: Die Darstellung der Anomeren von L-Rhamnopyranosylazid (3, 12) und 6-Desoxy-L-talopyranosylazid (8, 18) sowie von β-L-Fucopyranosylazid (21) wird beschrieben. Die 1H-NMR-Daten belegen eindeutig, daß die Verbindungen 3, 12, 18 und 22 sowie deren Acetate 2, 11, 19 und 21 in D2O- und CDCl3-Lösung nahezu ausschließlich in der 1C4(L)-Konformation vorliegen. Die Angliederung eines 2,2-Dimethyl-1,3-dioxolan-Ringes an die Hexopyranose in den Stellungen 2,3 oder 3,4 ruft eine Verzerrung der letzteren zu einer abgeflachten Sesselkonformation hervor. Es wird gezeigt, daß die chemischen Verschiebungen von 1-H and 2-H einen diagnostischen Wert bei der Zuordnung der Anomerenkonfiguration haben.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850112
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  • 9
    Electronic Resource
    Electronic Resource
    Heterocyclische Verbindungen aus Zuckern, X. Reaktion von D-Penicillamin mit Penta-O-acetyl-aldehydo-D-galaktose (1977)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 1536-1546 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic Compounds from Sugars, X. - Reaction of D-Penicillamine with Penta-O-acetyl-aldehydo-D-galactoseCondensation of D-penicillamine (1) and penta-O-acetyl-aldehydo-D-galactose (2) gives 5,5-dimethyl-2(R)- and 5,5-dimethyl-2(S)-(D-galacto-1′,2′,3′,4′,5′-pentaacetoxypentyl)thiazolidine-4(S)-carboxylic acid (3 and 8, respectively). The structures of these products were deduced from chemical reactions as well as from 1H-NMR and mass spectrometric data.
    Notes: Die Kondensation von D-Penicillamin (1) mit Penta-O-acetyl-aldehydo-D-galaktose (2) ergibt 5,5-Dimethyl-2(R)- und 5,5-Dimethyl-2(S)-(D-galakto-1′,2′,3′,4′,5′-pentaacetoxypentyl)thiazolidin-4(S)-carbonsäure (3 bzw. 8), deren Struktur durch chemische Umsetzungen, 1H-NMR-Spektroskopie sowie hochauflösende Massenspektroskopie bewiesen wird.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197719770915
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  • 10
    Electronic Resource
    Electronic Resource
    Heterocyclische Verbindungen aus Zuckern, IX. An C-2 epimere 2-(L-arabino-Tetrahydroxybutyl)-4(R)-thiazolidin-carbonsäuren (1976)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1976 (1976), S. 450-462 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocyclic Compounds from Sugars, IX.  -  2-(L-arabino-Tetrahydroxybutyl)-4(R)-thiazolidinecarboxylic Acids Epimeric at C-2Acetylation of 2(R)-(L-arabino-tetrahydroxybutyl)-4(R)-thiazolidinecarboxylic acid (3), prepared by reaction of L-arabinose (1) with L-cysteine (2), gives 3-acetyl-2(R)-(L-arabino-3′,4′-triacetoxybutyl)-4(R), 1′-thiazolidinecarbolactone (6) the structure of which was establish- ed by selective ring opening reactions. The reaction of tetra-0-acetyl-aldehyde-L-arabinose (13) with r-cysteine methyl ester (4) resulted mainly in the formation of methyl 2(R)-(L-arubino-tetraacetoxybutyl)-4(R)-thiazolidinecarboxylate (14). The epimeric methyl Z(S)-(r-arabino-tetraacetoxybutyl)-4(R)-thiazolidinecarboxylate (16) was obtained by esterification of 2(S)-(L-arabino-tetraacetoxybutyl)-4(R)-thiazolidinecarboxylic acid (15), which can be obtained from 13 by reaction with one equivalent of 2. -Reaction of 13 with excess 2 furnishes 3(?),5(S)-bis(L-arabino-l,2,3,4-tetraacetoxybutyl)-1H,3H,5H-dihydrothiazolo[3,4-c]oxazol-1- one (19). Mass and 13C-NMR spectroscopy were used to ascertain the structure of 19.
    Notes: Die Acetylierung der durch Reaktion von L-Arabinose (1) mit L-Cystein (2) herstellbaren 2(R)-(L-arabino-Tetrahydroxybutyl)-4(R)-thiazolidincarbonsäure(3) liefert 3-Acetyl-2(R)-(L-arabino-2′,3′,4′-triacetoxybutyl)-4(R),1′-thiazolidincarbolacton (6), dessen Struktur und Konformation durch die Ergebnisse selektiver Ringöffnungen bewiesen werden. Bei der Reaktion von Tetra-0-acetyl-aldehyde-r-arabinose (13) mit L-Cystein-methylester (4) entsteht überwiegend 2(R)-(L-arabino-Tetraacetoxybutyl)-4(R)-thiazolidincarbonsäure-methylester(14); der epimere 2(S)-(L-arabino-Tetraacetoxybutyl)-4(R)-thiazolidincarbonsäure-methylester(16) wird durch Umsetzung von 13 mit einer äquimolekularen Menge 2 und anschließende Veresterung der entstehenden 2(S)-(L-arabi-Tetraacetoxybutyl)-4(R)-thiazolidincarbonsäure (15) gewonnen. -Bei der Umsetzung von 13 mit überschüssigem 2 entsteht das 3(?),5(S)- Bis(L-arabino-l,2,3,4-Tetraacetoxybutyl)-1H,3H,5H-dihydrothiazolo[3,4-c]oxazol-1-on (19), dessen Struktur sich aus den Ergebnissen 13C-NMR- und massenspektroskopischer Unter- suchungen ergibt.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197619760310
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