Search results for: Hoe-Sup Byun

Items from 1 to 20 out of 26 results

article

Effect of ether glycerol lipids on interleukin-1β release and experimental autoimmune encephalomyelitis

Stephanie D. Boomkamp, Hoe-Sup Byun, Satvir Ubhi, Hui-Rong Jiang, more

Chemistry and Physics of Lipids > 2016 > 194 > C > 2-11

We have assessed the effect of two ether glycerol lipids, 77-6 ((2S, 3R)-4-(Tetradecyloxy)-2-amino-1,3-butanediol) and 56-5 ((S)-2-Amino-3-O-hexadecyl-1-propanol), which are substrates for sphingosine kinases, on inflammatory responses. Treatment of differentiated U937 macrophage-like cells with 77-6 but not 56-5 enhanced IL-1β release; either alone or in the presence of LPS. The stimulatory effect...

article

Practical multigram-scale synthesis of 4,6- and 4,8-sphingadienes, chemopreventive sphingoid bases

Hoe-Sup Byun, Robert Bittman

Chemistry and Physics of Lipids > 2012 > 165 > 7 > 794-801

Sphingadienes are chemopreventive agents that act by blocking signaling pathways that are activated in cancer. A practical synthesis of 4,6- and 4,8-sphingadienes on a scale of gram quantities is reported here in order to allow evaluation of the biological properties of these sphingolipids. The key steps in the preparation of 4,6-sphingadiene (1a) are an intramolecular cyclization of N-Boc derivative...

article

The sphingolipid degradation product trans-2-hexadecenal forms adducts with DNA

Pramod Upadhyaya, Ashok Kumar, Hoe-Sup Byun, Robert Bittman, more

Biochemical and Biophysical Research Communications > 2012 > 424 > 1 > 18-21

Sphingosine 1-phosphate, a bioactive signaling molecule with diverse cellular functions, is irreversibly degraded by the endoplasmic reticulum enzyme sphingosine 1-phosphate lyase, generating trans-2-hexadecenal and phosphoethanolamine. We recently demonstrated that trans-2-hexadecenal causes cytoskeletal reorganization, detachment, and apoptosis in multiple cell types via a JNK-dependent pathway...

article

Corrigendum to “The sphingolipid degradation product trans-2-hexadecenal induces cytoskeletal reorganization and apoptosis in a JNK-dependent manner” [Cell. Signal. 23(7) (2011) 1144-1152]

Ashok Kumar, Hoe-Sup Byun, Robert Bittman, Julie D. Saba

Cellular Signalling > 2012 > 24 > 1 > 351

article

Total Synthesis of α-1 C -Galactosylceramide, an Immunostimulatory C -Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis

Zheng Liu, Hoe-Sup Byun, Robert Bittman

The Journal of Organic Chemistry > 2011 > 76 > 21 > 8588 - 8598

article

The sphingolipid degradation product trans-2-hexadecenal induces cytoskeletal reorganization and apoptosis in a JNK-dependent manner

Ashok Kumar, Hoe-Sup Byun, Robert Bittman, Julie D. Saba

Cellular Signalling > 2011 > 23 > 7 > 1144-1152

The bioactive signaling molecule d-erythro-sphingosine-1-phosphate (S1P) is irreversibly degraded by the enzyme S1P lyase (SPL). The reaction of SPL with C18-S1P generates ethanolamine phosphate and a long-chain fatty aldehyde, trans-2-hexadecenal. Modulation of SPL expression in cells and organisms produces significant phenotypes, most of which have been attributed to corresponding changes in S1P-dependent...

article

Characterization of sphingosine-1-phosphate lyase activity by electrospray ionization–liquid chromatography/tandem mass spectrometry quantitation of (2E)-hexadecenal

Evgeny V. Berdyshev, Jonathan Goya, Irina Gorshkova, Glenn D. Prestwich, more

Analytical Biochemistry > 2011 > 408 > 1 > 12-18

Sphingosine-1-phosphate (S1P) is a sphingolipid signaling molecule crucial for cell survival and proliferation. S1P-mediated signaling is largely controlled through its biosynthesis and degradation, and S1P lyase (S1PL) is the only known enzyme that irreversibly degrades sphingoid base-1-phosphates to phosphoethanolamine and the corresponding fatty aldehydes. S1PL-mediated degradation of S1P results...

article

Selective deuterium labeling of the sphingoid backbone: facile syntheses of 3,4,5-trideuterio-d-erythro-sphingosine and 3-deuterio-d-erythro-sphingomyelin

Hoe-Sup Byun, Robert Bittman

Chemistry and Physics of Lipids > 2010 > 163 > 8 > 809-813

Deuteration at C-4 and C-5 of sphingosine was achieved via a hydrogen–deuterium exchange reaction of a β-ketophosphonate intermediate catalyzed by ND ₄ Cl in D ₂ O/tetrahydrofuran. To install deuterium at C-3 of sphingosine and sphingomyelin, sodium borodeuteride reduction/cerium(III) chloride reduction of an α,β-enone in perdeuteromethanol was used.

article

Asymmetric Synthesis of d - ribo -Phytosphingosine from 1-Tetradecyne and (4-Methoxyphenoxy)acetaldehyde

Zheng Liu, Hoe-Sup Byun, Robert Bittman

The Journal of Organic Chemistry > 2010 > 75 > 13 > 4356 - 4364

article

Synthesis of Immunostimulatory α- C -Galactosylceramide Glycolipids via Sonogashira Coupling, Asymmetric Epoxidation, and Trichloroacetimidate-Mediated Epoxide Opening

Zheng Liu, Hoe-Sup Byun, Robert Bittman

Organic Letters > 2010 > 12 > 13 > 2974 - 2977

article

Molecular features of phospholipids that affect glycolipid transfer protein-mediated galactosylceramide transfer between vesicles

Matts Nylund, Matti A. Kjellberg, Julian G. Molotkovsky, Hoe-Sup Byun, more

BBA - Biomembranes > 2006 > 1758 > 6 > 807-812

The glycolipid transfer protein (GLTP)-mediated movement of galactosylceramide from model membrane donor vesicles to acceptor vesicles is sensitive to the membrane environment surrounding the glycolipid. GLTP can catalyze the transfer of a fluorescently labeled GSL, anthrylvinyl-galactosylceramide (AV-GalCer), from vesicles composed of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine and dipalmitoylphosphatidylcholine...

article

The 3-Hydroxy Group and 4,5-trans Double Bond of Sphingomyelin Are Essential for Modulation of Galactosylceramide Transmembrane Asymmetry

Barbara Malewicz, Jacob T. Valiyaveettil, Kochurani Jacob, Hoe-Sup Byun, more

Biophysical Journal > 2005 > 88 > 4 > 2670-2680

The structural features of SPM that control the transbilayer distribution of β-GalCer in POPC vesicles were investigated by ¹³C- and ³¹P-NMR spectroscopy using lipid analogs that share physical similarities with GalCer or SPM. The SPM analogs included N-palmitoyl-4,5-dihydro-SPM, 3-deoxy-SPM, 1-alkyl-2-amidophosphatidylcholine, and dipalmitoylphosphatidylcholine, a popular model “raft lipid”. The...

article

The 4,5-Double Bond of Ceramide Regulates Its Dipole Potential, Elastic Properties, and Packing Behavior

Howard L. Brockman, Maureen M. Momsen, Rhoderick E. Brown, Linli He, more

Biophysical Journal > 2004 > 87 > 3 > 1722-1731

The biological activities of ceramides show a large variation with small changes in molecular structure. To help understand how the structure regulates the activity of this important lipid second messenger, we investigated the interfacial features of a series of synthetic ceramide analogs in monomolecular films at the argon-buffer interface. To minimize differences arising from the N-acyl moiety,...

article

Synthesis of l - lyxo -Phytosphingosine and Its 1-Phosphonate Analogue Using a Threitol Acetal Synthon

Xuequan Lu, Hoe-Sup Byun, Robert Bittman

The Journal of Organic Chemistry > 2004 > 69 > 16 > 5433 - 5438

article

Synthesis and Use of Novel Ether Phospholipid Enantiomers To Probe the Molecular Basis of the Antitumor Effects of Alkyllysophospholipids: Correlation of Differential Activation of c-Jun NH ₂ -Terminal Protein Kinase with Antiproliferative Effects in Neuronal Tumor Cells

Pranati Samadder, Robert Bittman, Hoe-Sup Byun, Gilbert Arthur

Journal of Medicinal Chemistry > 2004 > 47 > 10 > 2710 - 2713

article

Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate: Differential Interaction with Protein Targets

Xuequan Lu, Sandor Cseh, Hoe-Sup Byun, Gabor Tigyi, more

The Journal of Organic Chemistry > 2003 > 68 > 18 > 7046 - 7050

article

Synthesis and Growth Inhibitory Activity of Chiral 5-Hydroxy-2- N -Acyl-(3 E )-Sphingenines: Ceramides with an Unusual Sphingoid Backbone

Jiong Chun, Hoe-Sup Byun, Gilbert Arthur, Robert Bittman

The Journal of Organic Chemistry > 2003 > 68 > 2 > 355 - 359

article

First Asymmetric Synthesis of 6-Hydroxy-4-Sphingenine-Containing Ceramides. Use of Chiral Propargylic Alcohols To Prepare a Lipid Found in Human Skin

Jiong Chun, Hoe-Sup Byun, Robert Bittman

The Journal of Organic Chemistry > 2003 > 68 > 2 > 348 - 354

article

Preparation of chiral propargylic alcohols from α,β-unsaturated esters

Jiong Chun, Hoe-Sup Byun, Robert Bittman

Tetrahedron Letters > 2002 > 43 > 45 > 8043 - 8045

A series of chiral propargylic alcohols with high enantiomeric excess was prepared by asymmetric dihydroxylation of α,β-unsaturated esters, conversion of the diols to 4-(chloromethyl)-1,3-dioxolane intermediates, and base-induced elimination.

article

Stereochemical properties of lysophosphatidic acid receptor activation and metabolism

Kazuaki Yokoyama, Daniel L. Baker, Tamas Virag, Karoly Liliom, more

BBA - Molecular and Cell Biology of Lipids > 2002 > 1582 > 1-3 > 295-308

Ligand recognition by G protein-coupled receptors (GPCR), as well as substrate recognition by enzymes, almost always shows a preference for a naturally occurring enantiomer over the unnatural one. Recognition of lysophosphatidic acid (LPA) by its receptors is an exception, as both the natural l (R) and unnatural d (S) stereoisomers of LPA are equally active in bioassays. In contrast to the enantiomers...

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INFONA - science communication portal

Search results for: Hoe-Sup Byun

Effect of ether glycerol lipids on interleukin-1β release and experimental autoimmune encephalomyelitis

Practical multigram-scale synthesis of 4,6- and 4,8-sphingadienes, chemopreventive sphingoid bases

The sphingolipid degradation product trans-2-hexadecenal forms adducts with DNA

Corrigendum to “The sphingolipid degradation product trans-2-hexadecenal induces cytoskeletal reorganization and apoptosis in a JNK-dependent manner” [Cell. Signal. 23(7) (2011) 1144-1152]

Total Synthesis of α-1 C -Galactosylceramide, an Immunostimulatory C -Glycosphingolipid, and Confirmation of the Stereochemistry in the First-Generation Synthesis

The sphingolipid degradation product trans-2-hexadecenal induces cytoskeletal reorganization and apoptosis in a JNK-dependent manner

Characterization of sphingosine-1-phosphate lyase activity by electrospray ionization–liquid chromatography/tandem mass spectrometry quantitation of (2E)-hexadecenal

Selective deuterium labeling of the sphingoid backbone: facile syntheses of 3,4,5-trideuterio-d-erythro-sphingosine and 3-deuterio-d-erythro-sphingomyelin

Asymmetric Synthesis of d - ribo -Phytosphingosine from 1-Tetradecyne and (4-Methoxyphenoxy)acetaldehyde

Synthesis of Immunostimulatory α- C -Galactosylceramide Glycolipids via Sonogashira Coupling, Asymmetric Epoxidation, and Trichloroacetimidate-Mediated Epoxide Opening

Molecular features of phospholipids that affect glycolipid transfer protein-mediated galactosylceramide transfer between vesicles

The 3-Hydroxy Group and 4,5-trans Double Bond of Sphingomyelin Are Essential for Modulation of Galactosylceramide Transmembrane Asymmetry

The 4,5-Double Bond of Ceramide Regulates Its Dipole Potential, Elastic Properties, and Packing Behavior

Synthesis of l - lyxo -Phytosphingosine and Its 1-Phosphonate Analogue Using a Threitol Acetal Synthon

Synthesis and Use of Novel Ether Phospholipid Enantiomers To Probe the Molecular Basis of the Antitumor Effects of Alkyllysophospholipids: Correlation of Differential Activation of c-Jun NH ₂ -Terminal Protein Kinase with Antiproliferative Effects in Neuronal Tumor Cells

Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate: Differential Interaction with Protein Targets

Synthesis and Growth Inhibitory Activity of Chiral 5-Hydroxy-2- N -Acyl-(3 E )-Sphingenines: Ceramides with an Unusual Sphingoid Backbone

First Asymmetric Synthesis of 6-Hydroxy-4-Sphingenine-Containing Ceramides. Use of Chiral Propargylic Alcohols To Prepare a Lipid Found in Human Skin

Preparation of chiral propargylic alcohols from α,β-unsaturated esters

Stereochemical properties of lysophosphatidic acid receptor activation and metabolism

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