Papers by Dr. Lothar Hennig
Heterocycles, 2005
Isothiazolo[3,2-b]-1,3,4-oxadiazole-5,5-dioxide: Synthesis of a New Heteropentalene System. -Cycl... more Isothiazolo[3,2-b]-1,3,4-oxadiazole-5,5-dioxide: Synthesis of a New Heteropentalene System. -Cyclocondensation of 2-methyl-thiocyanato-2-butenal with aroyl hydrazides gives the novel azomethine imines (III). Their oxidation with hydrogen peroxide is studied under different reaction conditions. Electrocyclization of hydrosultams (V) derived from oxidation products IV) provides hitherto unknown heteropentalenes (VI). -(SCHMIDT, S.; KOLBERG, A.; HENNIG, L.; HUNGER, J.; SCHULZE*, B.; Heterocycles 65 (2005) 11, 2705-2720; Inst. Org. Chem., Univ. Leipzig, D-04103 Leipzig, Germany; Eng.) -Mais 13-141
Bioorganic Medicinal Chemistry, Jul 3, 2003
The interaction of a moenomycin derivative with the enzyme penicillin binding protein 1b (PBP 1b)... more The interaction of a moenomycin derivative with the enzyme penicillin binding protein 1b (PBP 1b) has been studied by means of STD NMR. The results obtained initiated the synthesis of a number of moenomycin derivatives modified in unit A including a moenomycin-ampicillin conjugate and determination of their antibiotic activities. A protocol is described that allows studying the interaction of moenomycin analogues with PBP 1b by fluorescence correlation spectroscopy. #
Journal of Natural Products, Feb 1, 2006
Tetrahedron, 1999
A disaccharide analogue () of moenomycin A lacking the OH group in the 4-position of the uronic a... more A disaccharide analogue () of moenomycin A lacking the OH group in the 4-position of the uronic acid moiety has been synthesized using the Saito deoxygenation reaction as key step. 13c does not inhibit the transglycosylase (PBP 1b), a key enzyme in the biosynthesis of bacterial peptidoglycan. The result demonstrates the importance of this OH group for the binding of disaccharide moenomycin analogues to the enzyme.Graphic
Heterocycles, 2006
ABSTRACT
Tetrahedron, 1997
On the way to a trisaccharide analogue of the antibiotic moenomycin A a trisaccharide intermediat... more On the way to a trisaccharide analogue of the antibiotic moenomycin A a trisaccharide intermediate has been prepared making use of a combination of Danishefsky's sulfonamidoglycosylation and the Schmidt trichloroacetimidate procedure.Graphic
Monatsh Chem, 2000
... the 3-carboxy group remains unaffected, the method can be applied for regioselective -functio... more ... the 3-carboxy group remains unaffected, the method can be applied for regioselective -functionalization of 3 ... acid derivatives by treatment with triethylsilane/trifluoroacetic acid in aone-pot procedure [10]. ... 4. The latter are doubly activated derivatives of N -methyl-,3-diamino ...
Synthesis Stuttgart, 2004
Starting from hexafluoroacetone-protected (S)-glutamic acid, trans-5-fluoropipecolic and 5,5-difl... more Starting from hexafluoroacetone-protected (S)-glutamic acid, trans-5-fluoropipecolic and 5,5-difluoropipecolic acid have been synthesized. The piperidine ring was constructed by an intramolecular metal carbenoid NH insertion.
Russ J Organ Chem, 2004
Chemistry of Diazocarbonyl Compounds. Part 10. Chemoselective O-Alkylation of 3(2H)-Oxoisothiazol... more Chemistry of Diazocarbonyl Compounds. Part 10. Chemoselective O-Alkylation of 3(2H)-Oxoisothiazole-1,1-dioxides with the Use of Rh(II)-Carbenoids. -Rh-catalyzed decomposition of diazo compounds (II) in the presence of saccharine or its analogues (I) provides enol ethers of oxoisothiazoles (III) (6 examples), formal products of diketocarbenoid insertion into the O-H bond of the enol form of 3-(2H)-oxoisothiazoles (I), instead of the expected N-alkylamides. -(SCHULZE, B.; NIKOLAEV, V. V.; HENNIG, L.; RODINA, L. L.; SIELER, J.; NIKOLAEV, V. A.; Russ.
Angewandte Chemie, 2002
f¸r die Hilfe bei der Durchf¸hrung der Experimente und der Deutschen Forschungsgemeinschaft der B... more f¸r die Hilfe bei der Durchf¸hrung der Experimente und der Deutschen Forschungsgemeinschaft der BC Biochemie GmbH, und dem Fonds der Chemischen Industrie f¸r finanzielle Unterst¸tzung.
Magn Reson Chem, 1998
The 1H and 13C chemical shifts of four apocampholenic aldehydes and the corresponding alcohols ar... more The 1H and 13C chemical shifts of four apocampholenic aldehydes and the corresponding alcohols are reported. 1998 John ( Wiley & Sons, Ltd.
Monatsh Chem, 2005
A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described st... more A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps -nucleophilic displacement reaction, Claisen, and finally Cope rearrangement -which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to -trifluoromethyl--ketoacids.
Cheminform, 2010
Exploratory Investigations into the Biosynthesis of the Antibiotic Moenomycin A. -The results of ... more Exploratory Investigations into the Biosynthesis of the Antibiotic Moenomycin A. -The results of a feeding experiment with 13 C-labeled sodium acetate are presented and discussed. -(ENDLER, K.; SCHURICHT, U.; HENNIG, L.; WELZEL, P.; HOLST, U.; ARETZ, W.; BOETTGER, D.; HUBER, G.; Tetrahedron Lett. 39 (1998) 1-2, 13-16; Inst. Org. Chem., Univ.
Heterocycles, 2004
Starting from hexafluoroacetone-protected (S)-glutamic acid, trans-5-fluoropipecolic and 5,5-difl... more Starting from hexafluoroacetone-protected (S)-glutamic acid, trans-5-fluoropipecolic and 5,5-difluoropipecolic acid have been synthesized. The piperidine ring was constructed by an intramolecular metal carbenoid NH insertion.
Monatshefte Fur Chemie Chemical Monthly, Feb 27, 2004
Cheminform, 2010
Two disaccharide analogues lb and 17a of moenomycin A have been synthesized and their antibiotic ... more Two disaccharide analogues lb and 17a of moenomycin A have been synthesized and their antibiotic and transglycosylase-inhibiting properties have been determined. The results permit for the first time to arrive at a general view of the structural requirements in this class of compounds necessary to elicit antibiotic activity.
Zeitschrift Fur Naturforschung B, 2011
Synthesis Stuttgart, 2003
Eur J Org Chem, 2003
ABSTRACT
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Papers by Dr. Lothar Hennig