scholarly journals Microbial metabolism of amino alcohols. Metabolism of ethanolamine and 1-aminopropan-2-ol in species of Erwinia and the roles of amino alcohol kinase and amino alcohol O-phosphate phospho-lyase in aldehyde formation

1973 ◽  
Vol 134 (4) ◽  
pp. 959-968 ◽  
Author(s):  
Alan Jones ◽  
Anne Faulkner ◽  
John M. Turner
Keyword(s):  
Aldehyde Dehydrogenase ◽  
Amino Alcohol ◽  
Erwinia Carotovora ◽  
Microbial Metabolism ◽  
Amino Alcohols ◽  
Growth Media ◽  
N Sources ◽  
N Source ◽  
Erwinia Ananas

1. Growth of Erwinia carotovora N.C.P.P.B. 1280 on media containing 1-aminopropan-2-ol compounds or ethanolamine as the sole N source resulted in the excretion of propionaldehyde or acetaldehyde respectively. The inclusion of (NH4)2SO4 in media prevented aldehyde formation. 2. Growth, microrespirometric and enzymic evidence implicated amino alcohol O-phosphates as aldehyde precursors. An inducibly formed ATP–amino alcohol phosphotransferase was partially purified and found to be markedly stimulated by ADP, unaffected by NH4+ ions and more active with ethanolamine than with 1-aminopropan-2-ol compounds. Amino alcohol O-phosphates were deaminated by an inducible phospho-lyase to give the corresponding aldehydes. This enzyme, separated from the kinase during purification, was more active with ethanolamine O-phosphate than with 1-aminopropan-2-ol O-phosphates. Activity of the phospho-lyase was unaffected by a number of possible effectors, including NH4+ ions, but its formation was repressed by the addition of (NH4)2SO4 to growth media. 3. E. carotovora was unable to grow with ethanolamine or 1-aminopropan-2-ol compounds as sources of C, the production of aldehydes during utilization as N sources being attributable to the inability of the microbe to synthesize aldehyde dehydrogenase. 4. Of seven additional strains of Erwinia examined similar results were obtained only with Erwinia ananas (N.C.P.P.B. 441) and Erwinia milletiae (N.C.P.P.B. 955).

scholarly journals Microbial metabolism of amino alcohols. Aminoacetone metabolism via 1-aminopropan-2-ol in Pseudomonas sp. N.C.I.B. 8858

1974 ◽  
Vol 138 (2) ◽  
pp. 263-276 ◽  
Author(s):  
Anne Faulkner ◽  
John M. Turner
Keyword(s):  
Nitrogen Source ◽  
Aldehyde Dehydrogenase ◽  
Amino Alcohol ◽  
Nitrogen Sources ◽  
Amino Alcohols ◽  
Phosphate Ester ◽  
Pseudomonas Sp ◽  
Propionate Metabolism ◽  
Nad Oxidoreductase ◽  
Aldehyde Dehydrogenase Activity

1. Pseudomonas sp. N.C.I.B. 8858 grew well on d- and l-1-aminopropan-2-ol and on aminoacetone. 2. Cell-free extracts possessed high activities of inducibly formed l-1-aminopropan-2-ol-NAD+ oxidoreductase, amino alcohol–ATP phosphotransferase, dl-1-aminopropan-2-ol O-phosphate phospho-lyase and aldehyde–NAD+ oxidoreductase, but no 1-aminopropan-2-ol racemase or d-1-aminopropan-2-ol-NAD+ oxidoreductase. 3. The amino alcohol kinase (activated by ADP) was non-stereospecific towards 1-aminopropan-2-ol and was one-third as active with ethanolamine. The phospho-lyase was active with l- and d-1-aminopropan-2-ol O-phosphate, but ethanolamine O-phosphate was only one-tenth as active as its higher homologues. The purified aldehyde dehydrogenase was active with propionaldehyde, acetaldehyde and also with methylglyoxal. The previously observed 2-oxo aldehyde dehydrogenase activity was considered to be due to the broadly specific aldehyde dehydrogenase. 4. Mutants of Pseudomonas sp. N.C.I.B. 8858 deficient in 1-aminopropan-2-ol kinase, 1-aminopropan-2-ol O-phosphate phospho-lyase, aldehyde dehydrogenase or an enzyme involved in propionate metabolism were incapable of growth on aminoacetone or 1-aminopropan-2-ol as carbon source, although all except the kinase- or phospho-lyasedeficient mutants could use these compounds and ethanolamine as nitrogen sources. The aldehyde dehydrogenase-deficient mutants produced copious amounts of propionaldehyde and acetaldehyde during growth on the corresponding amino alcohols. 5. The path of aminoacetone metabolism in Pseudomonas sp. N.C.I.B. 8858 was concluded to involve l-1-aminopropan-2-ol, the O-phosphate ester of this compound, propionaldehyde and propionate as obligatory intermediates. d-1-Aminopropan-2-ol was metabolized by the same route as the l-isomer, gratuitously inducing formation of the stereospecific l-1-aminopropan-2-ol dehydrogenase. 6. Extracts of the pseudomonad grown with ethanolamine as the nitrogen source were devoid of 1-aminopropan-2-ol dehydrogenase, the kinase and the phospho-lyase, but exhibited cobamide coenzyme-dependent deaminase activity. Mutants deficient in kinase or phospho-lyase (deaminating) grew well on ethanolamine as the nitrogen source. Ethanolamine deaminase was inactive with, but inhibited by, 1-aminopropan-2-ol.

ChemInform Abstract: Synthesis of 1,2- and 1,4-Amino Alcohols from 1,3-Dienes via Oxazines. Rearrangements of 1,4-Amino Alcohol Derivatives to Oxazolines.

ChemInform ◽  
2010 ◽  
Vol 41 (37) ◽  
pp. no-no
Author(s):  
Lukas Werner ◽  
Jason Reed Hudlicky ◽  
Martina Wernerova ◽  
Tomas Hudlicky
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols

scholarly journals Ammonia volatilization in no-till system in the south-central region of the State of Paraná, Brazil

2010 ◽  
Vol 34 (5) ◽  
pp. 1677-1684 ◽  
Author(s):  
Sandra Mara Vieira Fontoura ◽  
Cimélio Bayer
Keyword(s):  
Controlled Release ◽  
Central Region ◽  
Ammonia Volatilization ◽  
Nh3 Volatilization ◽  
The South ◽  
N Application ◽  
N Sources ◽  
South Central ◽  
N Source ◽  
No Till

Ammonia (NH3) volatilization can reduce the efficiency of urea applied to the surface of no-till (NT) soils. Thus, the objectives of this study were to evaluate the magnitude of NH3 losses from surface-applied urea and to determine if this loss justifies the urea incorporation in soil or its substitution for other N sources under the subtropical climatic conditions of South-Central region of Paraná State, Brazil. The experiment, performed over four harvesting seasons in a clayey Hapludox followed a randomized block design with four replicates. A single dose of N (150 kg ha-1) to V5 growth stage of corn cultivated under NT system was applied and seven treatments were evaluated, including surface-applied urea, ammonium sulfate, ammonium nitrate, urea with urease inhibitor, controlled-release N source, a liquid N source, incorporated urea, and a control treatment with no N application. Ammonia volatilization was evaluated for 20 days after N application using a semi-open static system. The average cumulative NH3 loss due to the superficial application of urea was low (12.5 % of the applied N) compared to the losses observed in warmer regions of Southeastern Brazil (greater than 50 %). The greatest NH3 losses were observed in dry years (up to 25.4 % of the applied N), and losses decreased exponentially as the amount of rainfall after N application increased. Incorporated urea and alternative N sources, with the exception of controlled-release N source, decreased NH3 volatilization in comparison with surface-applied urea. Urea incorporation is advantageous for the reduction of NH3 volatilization; however, other aspects as its low operating efficiency should be considered before this practice is adopted. In the South-Central region of Paraná, the low NH3 losses from the surface-applied urea in NT system due to wet springs and mild temperatures do not justify its replacement for other N sources.

scholarly journals Effects of different nitrogen sources on growth, chlorophyll concentration, nitrate reductase activity and carbon and nitrogen distribution in Araucaria angustifolia

2008 ◽  
Vol 20 (4) ◽  
pp. 295-303 ◽  
Author(s):  
Mário L. Garbin ◽  
Lúcia R. Dillenburg
Keyword(s):  
Nitrate Reductase ◽  
Tree Species ◽  
Nitrate Reductase Activity ◽  
Reductase Activity ◽  
Temperate Climate ◽  
Growth Media ◽  
Araucaria Angustifolia ◽  
Inorganic N ◽  
N Source ◽  
Young Leaves

The southern Brazilian highland plateau is a mosaic of two contrasting plant communities, Araucaria forests and grasslands, which differ in the relative abundances and spatial patterns of soil nitrate and ammonium. However, we still do not know the inorganic N preferences of one key species in this mosaic, Araucaria angustifolia, the dominant tree species in the Araucaria forests and an important tree species invading the adjacent grasslands. Growth responses measured in a greenhouse study demonstrated that the species prefers NH4+ over NO3- as an inorganic N source. When provided alone, NO3- induced N deficiency symptoms: increases in root: shoot ratio, root branching and leaf mass per area, thickening of the shoot apexes and decreased mass-based chlorophyll and N concentrations of the young leaves. Nitrate-based nutrition also affected the whole plant N and carbon (C) distribution: young leaves accumulated less N and showed a larger C:N ratio than mature leaves. The nitrate reductase activity (NRA) followed the pattern of root: shoot partitioning expected for temperate climate conifers (activity concentrated in roots). However, the presence of NRA even under sole NH4+ nutrition indicates that plants may show constitutive levels of the enzyme, or that low levels of NO3- (possibly formed by contamination of the growth media) can induce leaf NRA. We suggest that A. angustifolia has ammonium as a preferential inorganic N source, and that this preference may favor a more successful establishment in grassland than in forest areas.

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 8-Substituted 6-(4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepins

1982 ◽  
Vol 47 (11) ◽  
pp. 3077-3093 ◽  
Author(s):  
Karel Šindelář ◽  
Jiřina Metyšová ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Protiva ◽  
...  
Keyword(s):  
Secondary Amine ◽  
Amino Alcohol ◽  
Sodium Hydride ◽  
Amino Alcohols ◽  
Central Ring ◽  
Psychotropic Agents ◽  
High Degree ◽  
By Products ◽  
Antiapomorphine Effect ◽  
Central Depressant

2-(2-Fluorophenylthio)benzaldehydes IXa-c and 5-chloro-2-(2-fluorophenylthio)acetophenone were treated with 1-methyl-4-piperidylmagnesium chloride and 3-dimethylaminopropylmagnesium chloride, respectively, and the resulting amino alcohols VIa-c, XVII and XVIII were cyclized with sodium hydride in dimethylformamide. In addition to the title compounds Ia-c, XIX and XX, several types of by-products were obtained. Demethylation of compound Ib by the chloroformate method afforded the secondary amine IIb which was transformed to the amino alcohols IIIb and Vb. Compounds Ia-c are very potent neuroleptics with a high degree of central depressant and cataleptic activity. The amino alcohol Vb exhibits a very strong antiapomorphine effect in rats.

scholarly journals Continuous and convergent access to vicinyl amino alcohols

2015 ◽  
Vol 51 (82) ◽  
pp. 15133-15136 ◽  
Author(s):  
Tomoya Nobuta ◽  
Guozhi Xiao ◽  
Diego Ghislieri ◽  
Kerry Gilmore ◽  
Peter H. Seeberger
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Assembly System

A four module convergent chemical assembly system delivers two classes of vicinyl amino alcohol and five APIs.

Synthesis of 1,2-amino alcohols via catalytic C–H amidation of sp3 methyl C–H bonds

2014 ◽  
Vol 50 (81) ◽  
pp. 12073-12075 ◽  
Author(s):  
Taek Kang ◽  
Heejeong Kim ◽  
Jeung Gon Kim ◽  
Sukbok Chang
Keyword(s):  
Amino Alcohol ◽  
Amino Alcohols ◽  
Chelating Groups

A new route to 1,2-amino alcohols is presented by C–H amidation of sp3 methyl C–H bonds as a key step. Various alcohols were employed after converting them to removable ketoxime chelating groups. Iridium-catalyzed C–H amidation and following LAH reduction furnished β-amino alcohol products.

scholarly journals Microbial metabolism of amino alcohols. Biosynthetic utilization of ethanolamine for lipid synthesis by bacteria

1980 ◽  
Vol 186 (1) ◽  
pp. 13-19 ◽  
Author(s):  
S D Shukla ◽  
J M Turner
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Mycobacterium Smegmatis ◽  
Lipid Synthesis ◽  
Erwinia Carotovora ◽  
Radioactive Isotopes ◽  
Growth Media ◽  
Lipid Fractions ◽  
Base Moiety ◽  
Aldehyde Dehydrogenase Activity

1. Ten bacteria utilizing [2-14C]ethanol-2-amine as the sole or major source of nitrogen for growth on glycerol + salts medium incorporated radioactivity into a variety of bacterial substances. A high proportion was commonly found in lipid fractions, particularly in the case of Erwinia carotovora. 2. Detailed studies of [14C]ethanolamine incorporation into lipids by five bacteria, including E. carotovora, showed that all detectable lipids were labelled. Even where phosphatidylethanolamine was the major lipid labelled, radioactivity was predominantly in the fatty acid rather than the base moiety. The labelled fatty acids were identified in each case. 3. The addition of acetate to growth media decreased the incorporation of radioactivity from ethanolamine into both fatty acid and phosphatidyl-base fragments of lipids from all the bacteria except Mycobacterium smegmatis. Experiments with [3H]ethanolamine and [14C]acetate confirmed that unlabelled acetate decreased the incorporation of both radioactive isotopes into lipids, except in the case of M. smegmatis. 4. Enzyme studies suggested one of two metabolic routes between ethanolamine and acetyl-CoA for each of four bacteria. A role for ethanolamine O-phosphate was not obligatory for the incorporation of [14C]ethanolamine into phospholipids, but correlated with CoA-independent aldehyde dehydrogenase activity.

Photoredox catalysed synthesis of amino alcohol

2018 ◽  
Vol 42 (1) ◽  
pp. 688-691 ◽  
Author(s):  
Vishal Srivastava ◽  
Pravin K. Singh ◽  
Sudhanshu Kanaujia ◽  
Praveen P. Singh
Keyword(s):  
Visible Light ◽  
Amino Alcohol ◽  
Amino Alcohols ◽  
One Pot

A mild and efficient one-pot visible light-induced method has been developed for the synthesis of amino alcohols.

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