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TheScientificWorldJournal Jun 2010In this work, we report on the preparation and evaluation of the in vitro antileishmanial activity of a series of lipophilic aromatic aminoalcohols. All compounds were... (Review)
Review
In this work, we report on the preparation and evaluation of the in vitro antileishmanial activity of a series of lipophilic aromatic aminoalcohols. All compounds were assessed for their in vitro antiproliferative activity against promastigotes of three Leishmania species. The most lipophilic aminoalcohols bearing an aliphatic moiety with eight to 12 carbon atoms displayed a good activity against L. amazonensis and L. major, and two of them also showed antiproliferative activity against L. chagasi. The best results were obtained for the N-dodecanoyl ethylenediamine derivative and for N-decyl aminoalcohol (IC50=5.2 and 0.7 microM, respectively).
Topics: Amino Alcohols; Animals; Antiprotozoal Agents; Leishmania; Lipid Metabolism; Polyamines
PubMed: 20563528
DOI: 10.1100/tsw.2010.106 -
Journal of Lipid Research Jul 1969Phytoglycolipid has been isolated for the first time from plant leaves (Phaseolus vulgaris). The purified product (almost identical with the phytoglycolipid isolated...
Phytoglycolipid has been isolated for the first time from plant leaves (Phaseolus vulgaris). The purified product (almost identical with the phytoglycolipid isolated from flax seed) was a ceramide attached through phosphate diester linkage to an oligosaccharide, which consisted of the usual trisaccharide unit (inositol, hexuronic acid, hexosamine) to which were attached mannose, galactose, and arabinose. The major fatty acids were the saturated 2-hydroxy C(22), C(24), and C(26) acids; the major long-chain bases were dehydrophytosphingosine (d-ribo-1,3,4-trihydroxy-2-amino-8-trans-octadecene) (53%) and phytosphingosine (d-ribo-1,3,4-trihydroxy-2-amino-octadecane) (32%). A ceramide and a cerebroside were also isolated. In the ceramide the major fatty acids and the major long-chain bases were the same as in the phytoglycolipid. In the cerebroside, the fatty acid composition was similar to that in the ceramide and phytoglycolipid, but the long-chain bases consisted of dehydrophytosphingosine and phytosphingosine (7:1) with a substantial amount of unidentified long-chain base. The sugar component was glucose.
Topics: Amino Alcohols; Arabinose; Cellulose; Cerebrosides; Chemical Phenomena; Chemistry; Chromatography, Gas; Chromatography, Ion Exchange; Chromatography, Paper; Fatty Acids; Glycolipids; Hexoses; Inositol; Lipids; Methods; Oligosaccharides; Plants; Seeds; Species Specificity; Uronic Acids
PubMed: 5797522
DOI: No ID Found -
Journal of Visualized Experiments : JoVE Feb 2018Amino alcohols are versatile compounds with a wide range of applications. For instance, they have been used as chiral scaffolds in organic synthesis. Their synthesis by...
Amino alcohols are versatile compounds with a wide range of applications. For instance, they have been used as chiral scaffolds in organic synthesis. Their synthesis by conventional organic chemistry often requires tedious multi-step synthesis processes, with difficult control of the stereochemical outcome. We present a protocol to enzymatically synthetize amino alcohols starting from the readily available L-lysine in 48 h. This protocol combines two chemical reactions that are very difficult to conduct by conventional organic synthesis. In the first step, the regio- and diastereoselective oxidation of an unactivated C-H bond of the lysine side-chain is catalyzed by a dioxygenase; a second regio- and diastereoselective oxidation catalyzed by a regiodivergent dioxygenase can lead to the formation of the 1,2-diols. In the last step, the carboxylic group of the alpha amino acid is cleaved by a pyridoxal-phosphate (PLP) decarboxylase (DC). This decarboxylative step only affects the alpha carbon of the amino acid, retaining the hydroxy-substituted stereogenic center in a beta/gamma position. The resulting amino alcohols are therefore optically enriched. The protocol was successfully applied to the semipreparative-scale synthesis of four amino alcohols. Monitoring of the reactions was conducted by high performance liquid chromatography (HPLC) after derivatization by 1-fluoro-2,4-dinitrobenzene. Straightforward purification by solid-phase extraction (SPE) afforded the amino alcohols with excellent yields (93% to >95%).
Topics: Amino Alcohols; Catalysis; Dioxygenases; Lysine; Stereoisomerism
PubMed: 29553559
DOI: 10.3791/56926 -
The Biochemical Journal Aug 19731. 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...
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.
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 (NH(4))(2)SO(4) 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 NH(4) (+) 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 NH(4) (+) ions, but its formation was repressed by the addition of (NH(4))(2)SO(4) 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).
Topics: Acetaldehyde; Aldehydes; Amino Alcohols; Ammonia-Lyases; Ammonium Sulfate; Carbon Radioisotopes; Erwinia; Ethanolamines; Organophosphorus Compounds; Oxygen Consumption; Phosphotransferases; Propanolamines
PubMed: 4357716
DOI: 10.1042/bj1340959 -
Marine Drugs Jun 2014Seven new amino alcohol compounds, pseudoaminols A-G (1-7), were isolated from the ascidian Pseudodistoma sp. collected off the coast of Chuja-do, Korea. Structures of...
Seven new amino alcohol compounds, pseudoaminols A-G (1-7), were isolated from the ascidian Pseudodistoma sp. collected off the coast of Chuja-do, Korea. Structures of these new compounds were determined by analysis of the spectroscopic data and from chemical conversion. The presence of an N-carboxymethyl group in two of the new compounds (6 and 7) is unprecedented among amino alcohols. Several of these compounds exhibited moderate antimicrobial activity and cytotoxicity, as well as weak inhibitory activity toward Na+/K+-ATPase.
Topics: Amino Alcohols; Animals; Anti-Infective Agents; Antineoplastic Agents; Humans; Republic of Korea; Sodium-Potassium-Exchanging ATPase; Spectrum Analysis; Urochordata
PubMed: 24962272
DOI: 10.3390/md12063754 -
Nature Communications Feb 2021Evolution of xeno nucleic acid (XNA) world essentially requires template-directed synthesis of XNA polymers. In this study, we demonstrate template-directed synthesis of...
Evolution of xeno nucleic acid (XNA) world essentially requires template-directed synthesis of XNA polymers. In this study, we demonstrate template-directed synthesis of an acyclic XNA, acyclic L-threoninol nucleic acid (L-aTNA), via chemical ligation mediated by N-cyanoimidazole. The ligation of an L-aTNA fragment on an L-aTNA template is significantly faster and occurs in considerably higher yield than DNA ligation. Both L-aTNA ligation on a DNA template and DNA ligation on an L-aTNA template are also observed. High efficiency ligation of trimer L-aTNA fragments to a template-bound primer is achieved. Furthermore, a pseudo primer extension reaction is demonstrated using a pool of random L-aTNA trimers as substrates. To the best of our knowledge, this is the first example of polymerase-like primer extension of XNA with all four nucleobases, generating phosphodiester bonding without any special modification. This technique paves the way for a genetic system of the L-aTNA world.
Topics: Amino Alcohols; Base Pairing; Biocatalysis; Butylene Glycols; Cations, Divalent; DNA; DNA Primers; Imidazoles; Manganese; Nucleic Acid Conformation; Nucleic Acids; RNA; Solutions
PubMed: 33547322
DOI: 10.1038/s41467-021-21128-0 -
Canadian Medical Association Journal Feb 1972
Comparative Study
Topics: Adolescent; Adrenergic beta-Agonists; Adult; Aerosols; Aged; Airway Obstruction; Amino Alcohols; Asthma; Blood Pressure; Bronchitis; Bronchodilator Agents; Butylamines; Chronic Disease; Female; Heart Rate; Humans; Isoproterenol; Male; Middle Aged; Phenethylamines; Pulmonary Ventilation; Sympathomimetics; Vital Capacity
PubMed: 4400796
DOI: No ID Found -
British Medical Journal Dec 1971
Topics: Adrenergic beta-Antagonists; Adult; Amino Alcohols; Angina Pectoris; Humans; Male; Middle Aged; Myocardial Infarction; Resuscitation; Sympatholytics; Ventricular Fibrillation
PubMed: 4399701
DOI: 10.1136/bmj.4.5789.723 -
Nature Communications Jan 2018Enantiopure vicinal amino alcohols and derivatives are essential structural motifs in natural products and pharmaceutically active molecules, and serve as main chiral...
Enantiopure vicinal amino alcohols and derivatives are essential structural motifs in natural products and pharmaceutically active molecules, and serve as main chiral sources in asymmetric synthesis. Currently known asymmetric catalytic protocols for this class of compounds are still rare and often suffer from limited scope of substrates, relatively low regio- or stereoselectivities, thus prompting the development of more effective methodologies. Herein we report a dual catalytic strategy for the convergent enantioselective synthesis of vicinal amino alcohols. The method features a radical-type Zimmerman-Traxler transition state formed from a rare earth metal with a nitrone and an aromatic ketyl radical in the presence of chiral N,N'-dioxide ligands. In addition to high level of enantio- and diastereoselectivities, our synthetic protocol affords advantages of simple operation, mild conditions, high-yielding, and a broad scope of substrates. Furthermore, this protocol has been successfully applied to the concise synthesis of pharmaceutically valuable compounds (e.g., ephedrine and selegiline).
Topics: Aldehydes; Amino Alcohols; Catalysis; Chemistry Techniques, Synthetic; Lewis Acids; Light; Nitrogen Oxides; Oxidation-Reduction; Photochemical Processes; Stereoisomerism
PubMed: 29379007
DOI: 10.1038/s41467-017-02698-4 -
Journal of Enzyme Inhibition and... Dec 2021The synthesis and carbonic anhydrase (CA; EC 4.2.1.1) activating effects of a series of oxime ether-based amino alcohols towards four human (h) CA isoforms expressed in...
The synthesis and carbonic anhydrase (CA; EC 4.2.1.1) activating effects of a series of oxime ether-based amino alcohols towards four human (h) CA isoforms expressed in human brain, hCA I, II, IV and VII, are described. Most investigated amino alcohol derivatives induced a consistent activation of the tested CAs, with Ks spanning from a low micromolar to a medium nanomolar range. Specifically, hCA II and VII, putative main CA targets when central nervous system (CNS) diseases are concerned, were most efficiently activated by these oxime ether derivatives. Furthermore, a multitude of selective hCA VII activators were identified. As hCA VII is one of the key isoforms involved in brain metabolism and other brain functions, the identified potent and selective hCA VII activators may be considered of interest for investigations of various therapeutic applications or as lead compounds in search of even more potent and selective CA activators.
Topics: Amino Alcohols; Brain; Carbonic Anhydrases; Dose-Response Relationship, Drug; Ethers; Humans; Isoenzymes; Molecular Structure; Oximes; Structure-Activity Relationship
PubMed: 33103482
DOI: 10.1080/14756366.2020.1838501