Krueger, J. M.Overview
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Most widely held works by
J. M Krueger
Peptidoglycans as Promoters of Slow-Wave Sleep. II. Somnogenic and Pyrogenic Activities of Some Naturally Occurring Muramyl Peptides; Correlations with Mass Spectrometric Structure Determination
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Book
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1 edition published in 1984 in English and held by 1 library worldwide The structures of components of the sleep-promoting material purified from human urine were established by fast atom bombardment-mass spectrometry. We report here that two substances isolated from that preparation, viz. N-acetylglucosaminyl-1,6-anhydro-N-acetylmuramyl-Ala-gamma-Glu-diaminopimelyl-Ala) and that compound lacking the terminal alanine, are active as somnogens. Cerebro-intraventricular administration of 1 pmol of the glycotetrapeptide was sufficient to induce prolonged excess sleep in rabbits. Findings show that in addition to the muramyl form of peptidoglycan monomers, the anhydro muramyl form, with no reducing end, is compatible with somnogenic activity. Furthermore, the data obtained with a natural product amplify our earlier observations with smaller synthetic molecules of the importance of amidation/deamidation in the structure-activity relationships of muramyl peptides.
Peptidoglycans as Promoters of Slow-Wave Sleep. I. Structure of the Sleep-Promoting Factor Isolated from Human Urine
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Book
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1 edition published in 1984 in English and held by 1 library worldwide Fast atom bombardment-mass spectrometry (FAB-MS) has been used to determine the structure of the urinary sleep-promoting factor (FS), the nature of whose components had been reported earlier. Less than 1 nmol of the underivatized substance sufficed for the FABMS experiments. The major somnogenic constituent of the purified preparation was a peptidoglycan of Mr = 921 with the structure N-acetylglucosaminyl-N-acetylanhydromuramylalanylglutamyldiaminopi-melylalanine. The anhydro linkage is between C-1 and C-6 of the muramyl entity. Two additional substances accompanied the above compound. These were the hydrated form (i.e. in which the muramyl entity had a free reducing end, and a free hydroxyl on C-6), and an anhydro analogue lacking the terminal alanine. The Mr values were 939 and 850, respecitvely. Methyl esters were prepared, and these were also acetylated. The mass spectra of the methyl ester of Mr = 921 displayed an increase in Mr of 42 (i.e. 3 x 14), indicating the presence, originally, of three free carboxyls. Acetylation increased Mr by a further 168 units (i.e. 4 x 42), indicating 4 hydroxyl or amino groups. These data are consistent with the structure cited above for the main entity of FS. Similar confirmatory results were obtained for the two minor constituents described above. These operations were worked out on natural muramyl peptides of known structure, obtained from other sources, and the data are given for comparison.
Muramyl Peptides: Variation of Somnogenic Activity with Structure
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Book
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1 edition published in 1984 in English and held by 1 library worldwide
Sleep-Promoting Factor S: Purification and Properties
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Book
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1 edition published in 1978 in English and held by 1 library worldwide
Sleep-Promoting Material from Human Urine and Its Relation to Factor S from Brain
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Book
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1 edition published in 1979 in English and held by 1 library worldwide |
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