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  • 1995-1999  (16)
  • 1980-1984  (18)
  • General Chemistry  (27)
  • Inorganic Chemistry  (7)
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  • 1
    Electronic Resource
    Electronic Resource
    Thermolyse von Oxazolin-5-onen, X. 3-Imidazoline und Δ3-Tetrahydropyrimidine durch Thermolyse von 3-Oxazolin-5-onen aus N-Acyldipeptiden (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 770-786 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Thermolysis of Oxazolin-5-ones, X. 3-Imidazolines and Δ3-Tetrahydropyrimidines by Thermolysis of 3-Oxazolin-5-ones Derived from N-Acyl DipeptidesOn thermolysis 2-(acylaminomethyl)-3-oxazolin-5-ones (3a - g) undergo elimination of CO2 to give nitrile ylides which cyclize to 3-imidazolines 4a - g via intramolecular proton transfer. The 2-acylaminoethyl derivative 3h yields a Δ3-tetrahydropyrimidine 5h in an analogous manner. Compounds 3 may be easily obtained from N-acyl dipeptides 1. The temperature dependence of the 1H NMR spectra of 4 is discussed.
    Notes: Die Thermolyse von 2-(Acylaminomethyl)-3-oxazolin-5-onen (3a - g) führt unter Eliminierung von CO2 zu Nitril-yliden, welche nach innermolekularer Protonenübertragung zu 3-Imidazolinen 4a - g cyclisieren. Analog liefert das 2-(Acylaminoethyl)-Derivat 3h ein Δ3-Tetrahydropyrimidin 5h. Die Oxazolinone 3 sind aus N-Acyldipeptiden 1 leicht zugänglich. Die Temperaturabhängigkeit der 1H-NMR-Spektren von 4 wird diskutiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130234
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  • 2
    Electronic Resource
    Electronic Resource
    Metal Complexes of Biologically Important Ligands, XCl. Introduction of Organometallic Fragments into α-Amino Acids by Reactions of α-Bromoglycine Derivatives with Anionic Organotransition-Metal CompoundsDedicated to Professor Victor Gutmann on the occasion of his 75th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 171-177 
    Details
    ISSN: 0009-2940
    Keywords: α-Bromoglycine derivatives ; Amino acids ; Iron ; Chromium ; Tungsten ; Transition-metal-labeled α-amino acids ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reactions of protected α-bromoglycine esters R1(O)CNHCH(Br)CO2R2 (R1=Ph, OCMe3; R2 =Me, tBu) with organometallic anions of acetylferrocene, CpFe(CO)(PPh3)-C(O)CH3, (OC)5M=C(OMe)CH3 (M=Cr, W), (OC)3Cr(η6-diphenylmethane), (OC)3Cr[η6-fluorene), (OC)3Cr(η6-dihydroanthracene) and of (OC)3Cr(-η6aniline) and (OC)3Cr(η6-o-toluidine) provide a method for the introduction of organometallic fragments into the side chains of α-amino acids.The complexes may be useful as markers for α-amino acids in peptides.The compound (OC))3Cr(η-o-C6H4(CH3)NHC-(H)(CO2Me)NHC(O)Ph was characterized by X-ray diffraction.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971300206
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  • 3
    Electronic Resource
    Electronic Resource
    Reaktionen von Oxazolin-5-on-Anionen, IX. Ein einfaches Verfahren zur Darstellung von Derivaten der δ-Aminolävulinsäure und verwandter Verbindungen (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 787-790 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Oxazolin-5-one Anions, IX. A Simple Procedure for the Preparation of δ-Aminolevulinic Acid Derivatives and Related CompoundsCyclization of Z-dipeptides 1 with acetic anhydride leads to 2-oxazolin-5-ones, which yield the corresponding 3-oxazolin-5-ones 2 by base-catalyzed addition of ethyl acrylate or acrylonitrile. Hydrolysis of 2a gives ethyl δ-(benzyloxycarbonylamino)levulinate (3a), which may be converted into several N-protected derivatives 3e - i. Via the same procedure the homologue 3b and the nitriles 3c, d are easily obtained.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130235
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  • 4
    Electronic Resource
    Electronic Resource
    Metallkomplexe mit biologisch wichtigen Liganden, LXXXIXPart LXXXVIII: Ref.[1].. Oxidative Addition von elektrophilen α-Aminosäurederivaten an Platin(II)- und Cobalt(I)-Komplexe: α-Übergangsmetallierte AminosäurenHerrn Professor Dr. Hans Georg von Schnering zum 65. Geburtstag gewidmet. (1996)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 129 (1996), S. 1617-1620 
    Details
    ISSN: 0009-2940
    Keywords: α-Amino acid, α- and β-C-metallated ; Platinum(IV) complexes ; Cobaloxime complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Metal Complexes of Biologically Important Ligands, LXXXIXPart LXXXVIII: Ref.[1]. .  -  Oxidative Addition of Electrophilic Derivatives of α-Amino Acids to Platinum(II) and Cobalt(I) Complexes: α-Transition-Metallated Amino Acids Herrn Professor Dr. Hans Georg von Schnering zum 65. Geburtstag gewidmet.The addition of methyl α-bromohippurate to PtMe2(bipy) gives the α-metallated amino acid derivative (bipy)-Me2(Br)PtC(H)(NHCOPh)(CO2Me) as a mixture of isomers 1a, b of which the trans adduct 1a was characterized by X-ray diffraction. Methyl α-bromohippurate and N-Boc-O-tosylserine methyl ester are added to [Co(py)(DH)]- (DH = dimethylglyoxime, diphenylglyoxime) to give cobalt(III) complexes 2-5 with a cobalt-carbon bond.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19961291231
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  • 5
    Electronic Resource
    Electronic Resource
    Organometallic Complexes of Iridium, Palladium, Chromium and Iron from 2-Phenyl-5(4H)-oxazolones - Organometallic Labelled Dipeptides (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 485-493 
    Details
    ISSN: 1434-1948
    Keywords: 2-Phenyl-4-R-5(4H)-oxazolones ; Iridium ; Palladium ; Platinum ; Iron ; Chromium ; C-o,N-Bridging 2-phenyloxazolone ; Peptide labelling ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of 2-phenyl-4-R-5(4H)-oxazolones (R = Me, CH2Ph, CHMeEt) with [(η5-C5Me5)IrCl2]2 afforded the cyclometallated complexes (η5-C5Me5)(Cl)Ir(L) (1-3) [L = 2-phenyl-4-R-5(4H)-oxazolone(C-o,N)]. 2-Phenyl-5(4H)-oxazolone reacts with [(η5-C5Me5)IrCl2]2 and palladium(II) acetate to give complexes with a C-o,N-bridging oxazolone [(η5-C5Me5)(Cl)Ir]2(μ-Cl)(μ-L-H+) (4) and Pd3(μ-ac)5(μ-L-H+) (5). 2-Phenyloxazolone anions were added to the π ligands of [(η5-C6H7)Fe(CO)3]+ and [(η7-C7H7)Cr(CO)3]+ to give the adducts 6-11. Dipeptide derivatives 12-18 were obtained by reaction of 1, 2 and by reaction of the adduct 6 from [(η5-C6H7)Fe(CO)3]+; and the anion of 2-phenyloxazolone with α-amino acid esters. These reactions may be used for the labelling of peptides. Saponification of 15-18 yields the organometallic substituted peptide acids 19-22. Their dianions (deprotonation of COOH and peptide amide) were used as ligands towards (Ph3P)2PtCl2 to yield the bimetallic complexes 23-25. The structures of 4, 5, 9 and 10 were determined by X-ray diffraction.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Metabolites from the Wood-Rotting Basidiomycete Hapalopilusmutans (Aphyllophorales) (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1051-1055 
    Details
    ISSN: 1434-193X
    Keywords: Fungus ; Dihydroxybenzoic acids ; Benzoquinones ; Spirodiones ; Natural products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Fruit bodies of the wood-rotting North American fungus Hapalopilusmutans produce a mixture of dihydroxybenzoic acids 1, dihydroxybenzoquinones 2 and a novel type of spirodiones, e.g. mutadione A (4a). All compounds carry long alkyl chains, which may be partially unsaturated. The structures of the metabolites were established by spectroscopic methods.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Chromogenic Triterpenoids from Cortinarius fulvoincarnatus, C. sodagnitus and Related Toadstools (Agaricales) (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 255-260 
    Details
    ISSN: 1434-193X
    Keywords: Triterpenoids ; Sodagnitins ; Chromogens ; Toadstools ; Natural Products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Fruit-bodies of the toadstools Cortinarius sodagnitus,C. fulvoincarnatus, C. arcuatorum(Agaricales) show a remarkable ink-red colour reaction when treated with aqueous base. We isolated six chromogens, named the sodagnitins A-F, from the toadstools and elucidated their structures by spectroscopic techniques. The sodagnitins are triterpenoids of the malabaricane type with a highly modified side chain. A mechanism for the colour reaction is proposed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Total syntheses of the slime mold alkaloid arcyriacyanin APigments from Fungi, Part 67; Part 66: G. Mayer, G. Wille, W. Steglich, Tetrahedron Lett.1996, 26, 4483-4486. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 70-74 
    Details
    ISSN: 0947-6539
    Keywords: alkaloids ; Heck reactions ; heterocycles ; indoles ; total syntheses ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Arcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′-biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4-(triflyloxy)arcyriarubin 8 to N-methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3-bromo-4-[1-(tert-butoxycarbonyl)indol-3-yl]-1-methylmaleimide (9) and 4-bromoindole (10). The N-methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030112
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  • 9
    Electronic Resource
    Electronic Resource
    α-Aminosäuren als nucleophile Acyläquivalente, V. Sterisch gelenkte Michael-Addition von Oxazolin-5-on-Anionen an aktivierte Doppelbindungen; Synthese von1,4-Dicarbonylverbindungen und γ-Oxonitrilen (1981)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 114 (1981), S. 2580-2594 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: α-Amino Acids as Nucleophilic Acyl Equivalents, V. Sterically Directed Michael-Addition of Oxazolin-5-one Anions to Activated Double Bonds; Synthesis of 1-4-Dicarbonyl compounds and γ-OxonitrilesOxazolin-5-ones with bulky substituents like mesityl or 1-butylcyclohexyl at C-2 undergo triethyl-amine catalyzed addition to activated olefins exclusively at C-4. Hydrolysis of the derived 4,4-disubstituted 2-mesityl-2-oxazolin-5-ones 9 leads to N-mesitoyl amino acids 10 which yield 1,4-dicarbonyl compounds or γ-oxonitriles 11 on oxidation with lead tetraacetate.
    Notes: Oxazolin-5-one, die in 2-Stellung raumerfüllende Reste wie Mesityl oder 1-Butylcyclohexyl tragen, addieren in Gegenwart von Triethylamin aktivierte Olefine ausschließlich in 4-Stellung. Die so erhaltenen 4,4-disubstituierten 2-Mesityl-2-oxazolin-5-one 9 werden nach Hydrolyse zu den N-Mesitoylaminosäuren 10 mit Bleitetraacetat zu 1,4-Dicarbonylverbindungen oder γ-Oxonitrilen 11 oxidiert.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19811140721
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  • 10
    Electronic Resource
    Electronic Resource
    Tripodal Synthetic Peptide BundlesDedicated to Professor Wolfgang Beck on the occasion of his 65th birthday (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1254-1268 
    Details
    ISSN: 0947-6539
    Keywords: peptide bundles ; peptides ; pseudo-peptides ; template synthesis ; tripodal ligands ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The stereochemical course of the formation of the two diastereomers of trimethyl 2,2′,2″-nitrilotris[2-(benzoylamino)acetate], 2a and 2b, is described. The structures of both isomers were confirmed by X-ray diffraction studies. Diastereomer 2b could be obtained in larger quantities by epimerisation of 2 a to 2 b with catalytical amounts of NaOMe. The (RRR/SSS)-triester 2 b is a suitable template for the synthesis of tripodal peptide bundles. Saponification of 2 b yielded the C3-symmetrical racemic triacid 4 b, which was coupled with amino acid methyl esters and dipeptide esters to give pseudo-hexapeptides and pseudo-nonapeptides, respectively. The resulting mixtures of diastereomers were easily separated by crystallisation. Their absolute configuration at the template unit (RRR or SSS) was established by means of the CD spectra. The pseudo-hexapeptide (SSS)N(BzGly*ValOMe)3 (14) was saponified to yield the optically pure triacid (SSS)N(BzGly*ValOH)3 (23). Compound 23 is an ideally preorganised template for the production of longer tripodal peptides. This was illustrated by the synthesis of two pseudo-pentadecapeptides. Peptide bundles with polar side chains (histidine and serine) or end groups (catechol or hydroxamate units) were synthesised by using the templates 4 b, 22 and 23 as anchors.
    Additional Material: 14 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030813
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