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  • 1975-1979  (37)
  • 1955-1959  (4)
  • 1
    Electronic Resource
    Electronic Resource
    Ringschlüsse von Pyruvoylpeptiden und Dehydropeptiden Über Aminosäuren und Peptide, XXIV; Über Dehydroaminosäuren, XI (1978)
    Springer
    Monatshefte für Chemie 109 (1978), S. 147-155 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Further studies were made of the influence of structure on the ring closure reactionsA andB of pyruvoyl peptides and dehydropeptides. Pyruvoyl peptides can undergo aldol condensation (3 a-c) as an alternative to cyclization. Pyruvoyl tetrapeptide amides and dehydroalanyl tetrapeptide amides were synthesized. Formation of larger rings by insertion of an amide-NH into pyruvoyl carbonyl or the double bond of the dehydro amino acid respectively could not be detected.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00911954
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  • 2
    Electronic Resource
    Electronic Resource
    Photochemische Abspaltung von atomarem Schwefel aus Isothiocyanaten (1978)
    Springer
    Monatshefte für Chemie 109 (1978), S. 161-164 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Reaction rate, efficiency and back reaction of the photolysis of isothiocyanates yielding isonitriles and sulfur have been investigated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00911956
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  • 3
    Electronic Resource
    Electronic Resource
    Cis-Cycloprolylprolin-Anion-ein konfigurationsstabiles Carbanion (1975)
    Springer
    Monatshefte für Chemie 106 (1975), S. 313-320 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The racemisation ofcyclo-(l-Pro−l-Pro) (2) with metal amides in liq. ammonia was examined. The K-kation causes more extensive racemisation than Na-kation, which in turn is more effective than Li+. This, the racemisation of2 int-butyl alcohol with K+C6H5O− and the data gained from corresponding deuterated medium show that the racemisation of2 proceeds in two steps: in the first, the less stabletrans-cyclo-(l-Pro−d-Pro) (3) is formed, followed by the rapid conversion of3 to a mixture ofcyclo-(l-Pro−l-Pro) andcyclo-(d-Pro−d-Pro) in the second step.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00914523
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  • 4
    Electronic Resource
    Electronic Resource
    Notiz zur Synthese des optisch aktiven (—)-(2R,3R,6S,8S)-Nonactinsäure-methylesters (1975)
    Springer
    Monatshefte für Chemie 106 (1975), S. 219-222 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Using optically active propylene oxide (from lactic acid) methyl (−)-nonactate is prepared by way2→3→4→5→6→1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00914515
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  • 5
    Electronic Resource
    Electronic Resource
    Notiz zur Synthese des Nonactins (1975)
    Springer
    Monatshefte für Chemie 106 (1975), S. 1043-1044 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract With (−)-nonactic acid and the 8-epitosylate of benzyl (+)-nonactate usingWalden inversion (−)-nonactyl-(+)-nonactic acid is constructed. The latter forms by way of its imidazolide or its α-mercaptopyridyl ester the macrotetrolide nonactine in poor yield.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00900883
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  • 6
    Electronic Resource
    Electronic Resource
    Über Aminosäuren und Peptide, XV. Hydroxylsubstituierte Cyclodipeptide durch Ringschluß von Pyruvoylaminosäureamiden, II Zweifacher Ringschluß (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 2907-2916 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On Amino Acids and Peptides, XV. Formation of hydroxycyclodipeptides by Cyclization of Pyruvoyl Amino Acids, II. Double Cyclization2-Oxo-5-(pyruvoylamino)valeric methylamide (15) is synthesized via the compounds 10-14. 15 is stable in cristalline form and in chloroform solution, but affords the dihydroxycyclodipeptide 16 in dilute HCl solution by a double cyclization reaction. Further reaction with H2S/ZnCl2 and subsequent dehydrogenation yield the epidithio-cyclodipeptide 17. 1,2-Dehydroproline methylamide (23) is obtained by reaction of 5-azido-2-oxovaleric methylamide (22) with triphenylphosphine.
    Notes: 2-Oxo-5-(pyruvoylamino)valerian-methylamid (15) wird über die Stufen 10-14 aufgebaut. 15, in kristallinem Zustand und in Chloroformlösung stabil, bildet in verdünnter Chlorwasserstoffsäure durch zweifachen Ringschluß das Dihydroxy-cyclodipeptid 16. Reaktion mit H2S/ZnCl2 und folgende Dehydrierung führen von 16 zur Epidithioverbindung 17. 5-Azido2-oxovalerian-methylamid (22) wird mit Hilfe von Triphenylphosphin in 1,2-Dehydroprolinmethylamid (23) umgewandelt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080910
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  • 7
    Electronic Resource
    Electronic Resource
    Über Aminosäuren und Peptide, XVI. Über Dehydroaminosäuren, III. Additionen an α-Iminocarbonsäuren (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 2917-2922 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On Amino Acids and Peptides, XVI. On Dehydroamino Acids, III. Addition Reaction to α-iminocarboxylic AcidsAddition reactions to dehydroproline methyl ester (1) and dehydroproline methylamide (2) are described as examples for additions to α-iminocarboxylic acid derivatives. The addition products of carbonylchlorides (e. g. 6 and 7) are synthetically important as they allow to synthesize α-alkoxy-α-acylaminocarboxylic acids (10), α-acetylthio-α-acylaminocarboxylic acids (11), and α-acylamino-α,β-dehydrocarboxylic acids (12 and 13). The addition products of α-substituted carbonyl chlorides such as α-bromopropionyl chloride and pyruvoyl chloride to dehydroproline compounds (e. g. 14 and 17) lead to cyclodipeptides with α-alkoxy and α-mercapto functions (15, 16, 18, 19).
    Notes: Als Beispiele für Anlagerungsreaktionen an α-Iminocarbonsäurederivate werden Additionsreaktionen an Dehydroprolin-methylester (1) und Dehydroprolin-methylamid (2) beschrieben. Synthetisch wertvoll sind die Anlagerungsprodukte von Carbonsäurechloriden (z. B. 6 und 7), von denen Wege zu α-Alkoxy-α-acylaminocarbonsäuren (10), α-Acetylthio-α-acylaminocarbonsäuren (11) und α-Acylamino-α,β-dehydrocarbonsäuren (12 und 13) führen. Die Additionsprodukte α-substituierter Carbonsäurechloride wie α-Brompropionylchlorid und Pyruvoylchlorid an die Dehydroprolinverbindungen (z. B. 14 und 17) führen zu Cyclodipeptiden mit α-Alkoxy- und α-Mercaptofunktionen (15, 16, 18, 19).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080911
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  • 8
    Electronic Resource
    Electronic Resource
    Lichtreaktionen mit Carbonsäurederivaten, IX. Abfangversuche mit photochemisch erzeugtem monoatomarem und diatomarem Schwefel. Schwefeladdition an 1,2-Dimethylencyclohexan. - Synthese von 1,4,5,6,7,8-Hexahydrobenzo[d][1,2]dithiin und 1,3,4,5,6,7-Hexahydrobenzo[c]thiophen (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 630-639 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Photoreactions with Carbonic Acid Derivatives, IX. Experiments on the Capture of Photochemically Produced Monoatomic and diatomic sulfur-Sulfur Addition on 1,2-Dimethylenecyclohexane.-Synthesis of 1,4,5,6,7,8-Hexahydrobenzo-[d][1,2]dithiin and 1,3,5,6,7-Hexahydrobenzo[c]thiopheneIn addition to cis- and trans-2,3-diethoxy-2-butene (3) small amounts of 2,3-diethoxy-1-butene (6), 2,3-diethoxy-1,3-butadiene (7) and 1-ethoxy-1-ethanethiol (5) were found in the irradiation product of O-ethyl thioacetate. The produced sulfur adds to a slight extent to 1,2-Dimethylenecyclohexane giving 1,4,5,6,7,8-hexahydrobenzo[d][1,2]dithiin (8), 1,3,4,5,6,7-hexahydrobenzo-[c]thiophene (9) and 4,5,6,7-tetrahydrobenzo[c]thiophene (10). For definite identification of the reaction products 8, 9 and 10 were synthesized.
    Notes: Im Bestrahlungsprodukt von Thionessigsäure-äthylester (1) wurden neben cis- und trans-2,3-Diäthoxy-2-buten (3) in geringen Mengen noch 2,3-Diäthoxy-1-buten (6); 2,3-Diäthoxy-1,3-butadien (7) und α-Mercaptodiäthyläther (5) nachgewiesen. - Der gebildete Schwefel addiert sich in geringem Ausmaß an 1,2-Dimethylencyclohexan unter Bildung von 1,4,5,6,7,8-Hexahydrobenzo[d][1,2]dithiin (8), 1,3,4,5,6,7-Hexahydrobenzo[c]thiophen (9) und 4,5,6,7-Tetrahydrobenzo[c]thiophen (10). Zur sicheren Identifizierung der Reaktionsprodukte wurden 8, 9 und 10 synthetisiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080229
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  • 9
    Electronic Resource
    Electronic Resource
    Hochstereoselektive Totalsynthese des Nonactins1-3) (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 2628-2644 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Highly Stereoselective Total Synthesis of NonactinStarting with (S)-propylene oxide both enantiomeric methyl nonactinates 7a and 7b, and the corresponding benzyl esters 7α and 7β have been synthesized. The “diester” 14, consisting of the two enantiomeric nonactinic acids has been constructed via nucleophilic reaction of the potassium corboxylate and the ρ-toluenesulfonate using Walden inversion. In a similar way the “tetraester” 18 with alternating arrangement of the nonactinic acids was formed. Ring closure of the latter gave nonactin.
    Notes: Beginnend mit (S)-Propylenoxid werden die beiden enantiomeren Nonactinsäure-methylester 7a und 7b bzw. die entsprechenden Benzylester 7α und 7β aufgebaut. Durch nucleophile Esterbildung aus Tosylester und Kaliumcarboxylat unter Waldenscher Umkehr gelang es, den „Diester“ 14 aus zwei enantiomeren Nonactinsäuren und den „Tetraester“ 18 aus den alternierend angeordneten enantiomeren Nonactinsäuren zu synthetisieren. Ringschluß des „Tetraesters“ führte zum Nonactin.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761090734
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  • 10
    Electronic Resource
    Electronic Resource
    Über Aminosäuren und Peptide, XXVII: Über Dehydroaminosäuren, XIV: Biomimetische Versuche zur Cysteinbildung. Addition von SH-Verbindungen an Dehydroaminosäuren (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 1058-1076 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On Amino Acids and Peptides, XXVI:I On Dehydroamino Acids, XIV: Biomimetic Experiments on Cysteine Synthesis Addition of SH-Compounds to Dehydroamino Acids1The stereoselectivity of thiol addition to dehydrodipeptides was examined under various conditions. Thiolate-catalyzed addition of thiols to dehydroalanyl-prolineamides (7-10) results in formation of D-cysteinyl-peptides with high optical yields. Almost no stereoselectivity is found during addition to the analogous dehydroalanyl-peptides, containing L-proline ester (11) or L-prolinol (12), to the prolyl-dehydroalanine peptide 14, and to dehydroalanylpeptides containing valine (17) or alanine (16) instead of proline.2The thiol addition to several dehydrovaline compounds 21 to 26 was investigated as a model for the metabolic addition reactions to aminoacrylic acids. Especially to salicylidene-, p-nitrosalicylidene-, and the pyridoxylidene dehydrovaline esters (22, 23, and 26) thiols were added 10 to 30 times faster than to dehydrovaline-, N-acetyldehydrovaline-, and benzylidenedehydrovaline ester (24, 25, and 21).
    Notes: 1Die Stereoselektivität der Thioladdition an Dehydrodipeptide in Abhängigkeit von Struktur und Reaktionsbedingungen wurde untersucht. Bei thiolat-katalysierter Addition von Thiolen an die Dehydroalanyl-prolinamide (7-10) wird mit hoher optischer Induktion das D-Cysteinylpeptid gebildet; nahezu keine Induktion wird bei den analogen Dipeptiden mit einer Ester- oder einer Alkoholfunktion (11 bzw. 12), bei umgekehrter Anordnung von Prolin- und Dehydroalanin-Einheit (14) und bei Ersatz der Prolinhälfte durch Alanin (16) oder Valin (17) beobachtet.2Als Modell für Additionsreaktionen an Aminoacrylsäuren im Aminosäuremetabolismus wurde die Thioladdition an verschiedene Dehydrovalinverbindungen 21-26 untersucht. Dabei addierten Salicyliden-, p-Nitrosalicyliden- und Pyridoxyliden-dehydrovalinester (22, 23, 26) Thiole 10- bis 30 mal schneller als Dehydrovalin-, N-Acetyldehydrovalin- und N-Benzylidendehydrovalinester (24, 25, 21).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110325
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