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Synthesis of Three 3-C-Hydroxymethylpentoses with the D-ribo-, D-xylo- and L-lyxo-Configurations. Identification of the Latter with a Monosaccharide Isolated from Phase I Coxiella burnetii Lipopolysaccharide

  1. TitleSynthesis of Three 3-C-Hydroxymethylpentoses with the D-ribo-, D-xylo- and L-lyxo-Configurations. Identification of the Latter with a Monosaccharide Isolated from Phase I Coxiella burnetii Lipopolysaccharide
    Author Dahlman O.
    Co-authors Garegg J.P.

    		Mayer H.

    		Schramek Štefan SAVVIR - Virologický ústav SAV

    Source documentActa Chemica Scandinavica B. Roč. 40, č. 1 (1986), s. 15-20
    Languageeng - English
    CountrySE - Sweden
    Document kindrozpis článkov z periodík (rbx)
    UDC547.458.8, 577.11.114, 616.927, 579.88
    Keywordssyntéza 3-C-hydroxymetylpentóz * lipopolysacharid * coxiella burnetii * výskum základný
    CitationsIGA, D.P. - POPESCU, D. - GITMAN, S. Alternate Modulation of Biological Activity of Stress Molecule, beta-D-glucopyranosyl-cholesterol, by Chemical Modification of Sugar Moiety Hypotheses concerning biochemical meaning of the new glycosides. In REVISTA DE CHIMIE. ISSN 0034-7752, NOV 2019, vol. 70, no. 11, p. 3987-3990.
    PASARI, S. - MANMODE, S. - WALKE, G. - HOTHA, S. A Versatile Synthesis of Pentacosafuranoside Subunit Reminiscent of Mycobacterial Arabinogalactan Employing One Strategic Glycosidation Protocol. In CHEMISTRY-A EUROPEAN JOURNAL. ISSN 0947-6539, JAN 24 2018, vol. 24, no. 5, p. 1128-1139.
    MARKOVIC, M. - KOOS, P. - CARNY, T. - SOKOLIOVA, S. - BOHACIKOVA, N. - MONCOL, J. - GRACZA, T. Total Synthesis, Configuration Assignment, and Cytotoxic Activity Evaluation of Protulactone A. In JOURNAL OF NATURAL PRODUCTS. ISSN 0163-3864, MAY 2017, vol. 80, no. 5, p. 1631-1638.
    THIESEN, L.J.H. - CABRAL, N. - SILVA, M.J.E. - BEZERRA, G. - DOBOSZEWSKI, B. Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer. In ARKIVOC. ISSN 1551-7004, 2017, 4, p. 249-264.
    BERA, S. - CHATTERJEE, B. - MONDAL, D. Construction of quaternary stereocentres on carbohydrate scaffolds. In RSC ADVANCES. ISSN 2046-2069, 2016, vol. 6, no. 81, p. 77212-77242.
    GITMAN, S.S. - DUICA, F. - NICOLESCU, A. - IGA, D.P. Partial Methylation of Monosaccharides for the Elaboration of a Chromatographic Model Used in the Systematic Plant and Microorganisms as well as for Glycosylation. In REVISTA DE CHIMIE. ISSN 0034-7752, OCT 2015, vol. 66, no. 10, p. 1632-1635.
    ISLAM, M. - GAYATRI, G. - HOTHA, S. Influence of Steric Crowding on Diastereoselective Arabinofuranosylations. In JOURNAL OF ORGANIC CHEMISTRY. ISSN 0022-3263, AUG 21 2015, vol. 80, no. 16, p. 7937-7945.
    EVDOKIMOV, N.M. - CLARK, P.M. - FLORES, G. - CHAI, T. - FAULL, K.F. - PHELPS, M.E. - WITTE, O.N. - JUNG, M.E. Development of 2-Deoxy-2-[F-18]fluororibose for Positron Emission Tomography Imaging Liver Function in Vivo. In JOURNAL OF MEDICINAL CHEMISTRY. ISSN 0022-2623, JUL 23 2015, vol. 58, no. 14, p. 5538-5547.
    TURKS, M. - VEZE, K. - KISELOVS, G. - MACKEVICA, J. - LUGININA, J. - MISHNEV, A. - MARKOVIC, D. Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, JUN 4 2014, vol. 391, p. 82-88.
    SOARES, F.D. - SILVA, M.J.E. - DOBOSZEWSKI, B. Deoxygenation at the C3 position of D- and L-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, OCT 18 2013, vol. 380, p. 143-148.
    MANTA, S. - XIPNITOU, A. - KIRITSIS, C. - KANTSADI, A.L. - HAYES, J.M. - SKAMNAKI, V.T. - LAMPRAKIS, C. - KONTOU, M. - ZOUMPOULAKIS, P. - ZOGRAPHOS, S.E. - LEONIDAS, D.D. - KOMIOTIS, D. 3 '-Axial CH2OH Substitution on Glucopyranose does not Increase Glycogen Phosphorylase Inhibitory Potency. QM/MM-PBSA Calculations Suggest Why. In CHEMICAL BIOLOGY & DRUG DESIGN. ISSN 1747-0277, MAY 2012, vol. 79, no. 5, p. 663-673.
    ABRONINA, P.I. - PODVALNYY, N.M. - SEDINKIN, S.L. - FEDINA, K.G. - ZININ, A.I. - CHIZHOV, A.O. - TORGOV, V.I. - KONONOV, L.O. A Practical Silicon-Free Strategy for Differentiation of Hydroxy Groups in Arabinofuranose Derivatives. In SYNTHESIS-STUTTGART. ISSN 0039-7881, APR 2012, vol. 44, no. 8, p. 1219-1225.
    DOBOSZEWSKI, B. - SILVA, M.J.E. - NAZARENKO, A.Y. - NEMYKIN, V.N. 3-Deoxy-1,2-di-O-isopropylidene-5-O-tosyl-D-threo-pentofuranose. In ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS. ISSN 2056-9890, APR 2012, vol. 68, 4, p. O1109-+.
    DOBOSZEWSKI, B. - HERDEWIJN, P. Simple approach to 1-O-protected (R)- and (S)-glycerols from L- and D-arabinose for glycerol nucleic acids (GNA) monomers research. In TETRAHEDRON LETTERS. ISSN 0040-4039, JUL 27 2011, vol. 52, no. 30, p. 3853-3855.
    KNIJNENBURG, A.D. - TUIN, A.W. - SPALBURG, E. - DE NEELING, A.J. - MARS-GROENENDIJK, R.H. - NOORT, D. - OTERO, J.M. - LLAMAS-SAIZ, A.L. - VAN RAAIJ, M.J. - VAN DER MAREL, G.A. - OVERKLEEFT, H.S. - OVERHAND, M. Exploring the Conformational and Biological Versatility of beta-Turn-Modified Gramicidin S by Using Sugar Amino Acid Homologues that Vary in Ring Size. In CHEMISTRY-A EUROPEAN JOURNAL. ISSN 0947-6539, MAR 2011, vol. 17, no. 14, p. 3995-4004.
    PODVALNYY, N.M. - SEDINKIN, S.L. - ABRONINA, P.I. - ZININ, A.I. - FEDINA, K.G. - TORGOV, V.I. - KONONOV, L.O. Ring opening of acylated beta-D-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, JAN 3 2011, vol. 346, no. 1, p. 7-15.
    VARVOGLI, A.A.C. - KARAGIANNIS, I.N. - KOUMBIS, A.E. Efficient synthesis of syringolides, secosyrins, and syributins through a common approach. In TETRAHEDRON. ISSN 0040-4020, JAN 31 2009, vol. 65, no. 5, p. 1048-1058.
    DOBOSZEWSKI, B. - HERDEWIJN, P. Carbohydrate chiral-pool approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates. In TETRAHEDRON. ISSN 0040-4020, JUN 2 2008, vol. 64, no. 23, p. 5551-5562.
    LOPEZ-ORTEGA, B. - JENKINSON, S.F. - CLARIDGE, T.D.W. - FLEET, G.W.J. Oxetane amino acids: synthesis of tetrameric and hexameric carbopeptoids derived from L-ribo 4-(aminomethyl)-oxetan-2-carboxylic acid. In TETRAHEDRON-ASYMMETRY. ISSN 0957-4166, MAY 1 2008, vol. 19, no. 8, p. 976-983.
    DOBOSZEWSKI, B. - HERDEWIJN, P. Carbohydrate-based approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates. In TETRAHEDRON LETTERS. ISSN 0040-4039, FEB 18 2008, vol. 49, no. 8, p. 1331-1335.
    DE OLIVEIRA, M.T. - HUGHES, D.L. - NEPOGODIEV, S.A. - FIELD, R.A. Indirect approach to C-3 branched 1,2-cis-glycofuranosides: synthesis of aceric acid glycoside analogues. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, FEB 4 2008, vol. 343, no. 2, p. 211-220.
    BERCIER, A. - PLANTIER-ROYON, R. - PORTELLA, C. Convenient conversion of wheat hemicelluloses pentoses (D-xylose and L-arabinose) into a common intermediate. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, NOV 26 2007, vol. 342, no. 16, p. 2450-2455.
    NEPOGODIEV, S.A. - JONES, N.A. - FIELD, R.A. Plant Cell Wall Glycans: Chemical Synthesis of the Branched Sugar Aceric Acid. In FRONTIERS IN MODERN CARBOHYDRATE CHEMISTRY. ISSN 0097-6156, 2007, vol. 960, p. 34-49.
    SMELLIE, I.A. - BHAKTA, S. - SIM, E. - FAIRBANKS, A.J. Synthesis of putative chain terminators of mycobacterial arabinan biosynthesis. In ORGANIC & BIOMOLECULAR CHEMISTRY. ISSN 1477-0520, 2007, vol. 5, no. 14, p. 2257-2266.
    PAQUETTE, L.A. - ZHANG, Y.L. From common carbohydrates to enantiopure cyclooctane polyols and glycomimetics via deoxygenative zirconocene ring contraction. In JOURNAL OF ORGANIC CHEMISTRY. ISSN 0022-3263, JUN 9 2006, vol. 71, no. 12, p. 4353-4363.
    GAUBERT, G. - BABU, B.R. - VOGEL, S. - BRYLD, T. - VESTER, B. - WENGEL, J. Synthesis and RNA-selective hybridization of alpha-L-ribo- and beta-D-lyxo-configured oligonucleotides. In TETRAHEDRON. ISSN 0040-4020, MAR 6 2006, vol. 62, no. 10, p. 2278-2294.
    JONES, N.A. - NEPOGODIEV, S.A. - MACDONALD, C.J. - HUGHES, D.L. - FIELD, R.A. Synthesis of the branched-chain sugar aceric acid: A unique component of the pectic polysaccharide rhamnogalacturonan-II. In JOURNAL OF ORGANIC CHEMISTRY. ISSN 0022-3263, OCT 14 2005, vol. 70, no. 21, p. 8556-8559.
    PAQUETTE, L.A. - KIM, I.H. - CUNIERE, N. Zirconocene-mediated route to enantiopure 9-oxabicyclononanes functionalized on both carbon bridges. In ORGANIC LETTERS. ISSN 1523-7060, JAN 23 2003, vol. 5, no. 2, p. 221-223.
    GURJAR, M.K.Z. - BERA, S. Carbohydrate-based synthesis of naturally occurring marine metabolites slagenins B and C. In ORGANIC LETTERS. ISSN 1523-7060, OCT 17 2002, vol. 4, no. 21, p. 3569-3570.
    FUNABASHI, M. - OOSHIRO, Y. A multi-gram synthesis of 1,2 : 5,6-di-O-isopropylidene-3-C-trimethylsilylmethyl-alpha-D-allofuranose. An improved preparation of 3-C-hydroxymethyl-alpha-D-gluco- and 3-C-methyl-alpha-D-allofuranose derivatives. In ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL. ISSN 0030-4948, AUG 2002, vol. 34, no. 4, p. 432-435.
    PAQUETTE, L.A. - CUNIERE, N. Diastereoselectivity control in the zirconocene-mediated ring contraction of 4-vinylfuranosides to enantiopure multiply functionalized cyclobutanes. In ORGANIC LETTERS. ISSN 1523-7060, MAY 30 2002, vol. 4, no. 11, p. 1927-1929.
    NIELSEN, P. - CHRISTENSEN, N.K. - DALSKOV, J.K. alpha-LNA (locked nucleic acid with alpha-D-configuration): Synthesis and selective parallel recognition of RNA. In CHEMISTRY-A EUROPEAN JOURNAL. ISSN 0947-6539, FEB 2 2002, vol. 8, no. 3, p. 712-722.
    SORENSEN, M.H. - NIELSEN, C. - NIELSEN, P. Synthesis of a bicyclic analogue of AZT restricted in an unusual O4'-endo conformation. In JOURNAL OF ORGANIC CHEMISTRY. ISSN 0022-3263, JUL 13 2001, vol. 66, no. 14, p. 4878-4886.
    BARROS, M.T. - MAYCOCK, C.D. - THOMASSIGNY, C. Bromine in methanol: An efficient reagent for the deprotection of the tert-butyldiphenylsilyl group. In SYNLETT. ISSN 0936-5214, JUL 2001, no. 7, p. 1146-1148.
    MEREYALA, H.B. - HOTHA, S. - GURJAR, M.K. Synthesis of pentaarabinofuranosyl structure motif a of Mycobacterium tuberculosis. In CHEMICAL COMMUNICATIONS. ISSN 1359-7345, MAR 21 1998, no. 6, p. 685-686.
    TOMAN, R. - SKULTETY, L. - FTACEK, P. - HRICOVINI, M. NMR study of virenose and dihydrohydroxystreptose isolated from Coxiella burnetii phase I lipopolysaccharide. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, JAN 1998, vol. 306, no. 1-2, p. 291-296.
    KHOO, K.H. - SUZUKI, R. - DELL, A. - MORRIS, H.R. - MCNEIL, M.R. - BRENNAN, P.J. - BESRA, G.S. Chemistry of the lyxose-containing mycobacteriophage receptors of Mycobacterium phlei Mycobacterium smegmatis. In BIOCHEMISTRY. ISSN 0006-2960, SEP 10 1996, vol. 35, no. 36, p. 11812-11819.
    DOBOSZEWSKI, B. - HERDEWIJN, P. Branched-chain nucleosides: Synthesis of 3'-deoxy-3'-C-hydroxymethyl-alpha-L-lyxopyranosyl thymine and 3'-deogy-3'-C-hydroxymethyl-alpha-L-threofuranosyl thymine.. In TETRAHEDRON. ISSN 0040-4020, JAN 29 1996, vol. 52, no. 5, p. 1651-1668.
    LEE, J. - SHARMA, R. - WANG, S.M. - MILNE, G.W.A. - LEWIN, N.E. - SZALLASI, Z. - BLUMBERG, P.M. - GEORGE, C. - MARQUEZ, V.E. Conformationally constrained analogues of diacylglycerol .12. Ultrapotent protein kinase C ligands based on a chiral 4,4-disubstituted heptono-1,4-lactone template. In JOURNAL OF MEDICINAL CHEMISTRY. ISSN 0022-2623, JAN 5 1996, vol. 39, no. 1, p. 36-45.
    DOBOSZEWSKI, B. - HERDEWIJN, P.A.M. Synthesis of 4-deoxy-4-C-hydroxymethyl-alpha-L-lyxopyranosyl thymine. In NUCLEOSIDES & NUCLEOTIDES. ISSN 0732-8311, 1996, vol. 15, no. 9, p. 1495-1518.
    PAKULSKI, Z. - ZAMOJSKI, A. THE REACTION OF ACETYLIRON [(ETA-5-C5H5)FE(CO)(PPH(3))(COCH3)] WITH SUGAR ALDEHYDES - NEW SYNTHESIS OF DEOXYSUGARS. In TETRAHEDRON. ISSN 0040-4020, JAN 16 1995, vol. 51, no. 3, p. 871-908.
    CHAMBERLAIN, S.D. - BIRON, K.K. - DORNSIFE, R.E. - AVERETT, D.R. - BEAUCHAMP, L. - KOSZALKA, G.W. AN ENANTIOSPECIFIC SYNTHESIS OF THE HUMAN CYTOMEGALOVIRUS ANTIVIRAL AGENT [(R)-3-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)-4-HYDROXYBUTYL ]PHOSPHONIC ACID. In JOURNAL OF MEDICINAL CHEMISTRY. ISSN 0022-2623, APR 29 1994, vol. 37, no. 9, p. 1371-1377.
    SHARMA, R. - MARQUEZ, V.E. RAPID SYNTHESIS OF 5-O-(TERT-BUTYLDIPHENYLSILYL)-2-DEOXY-L-RIBONOLACTONE. In SYNTHETIC COMMUNICATIONS. ISSN 0039-7911, 1994, vol. 24, no. 13, p. 1937-1945.
    LOPEZ, J.C. - LAMEIGNERE, E. - BURNOUF, C. - LABORDE, M.D. - GHINI, A.A. - OLESKER, A. - LUKACS, G. EFFICIENT ROUTES TO PYRANOSIDIC HOMOLOGATED CONJUGATED ENALS AND DIENES FROM MONOSACCHARIDES. In TETRAHEDRON. ISSN 0040-4020, AUG 27 1993, vol. 49, no. 35, p. 7701-7722.
    LEE, J.W. - MARQUEZ, V.E. - LEWIN, N.E. - BLUMBERG, P.M. SYNTHESIS OF 2 RIGID DIACYLGLYCEROL ANALOGS HAVING A PERHYDRO FURO[3,4-B]FURAN BIS-GAMMA-BUTYROLACTONE SKELETON .2.. In TETRAHEDRON LETTERS. ISSN 0040-4039, JUL 2 1993, vol. 34, no. 27, p. 4313-4316.
    ANGYAL, S.J. CONFORMATIONAL-ANALYSIS IN CARBOHYDRATE-CHEMISTRY .6. A NEW TYPE OF ANHYDRO SUGAR - 1,3(1)-ANHYDRO-3-C-HYDROXYMETHYLALDOSES. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, SEP 2 1991, vol. 216, p. 171-178.
    GENUDELLAC, C. - GOSSELIN, G. - IMBACH, J.L. PREPARATION OF NEW ACYLATED DERIVATIVES OF L-ARABINOFURANOSE AND 2-DEOXY-L-ERYTHRO-PENTOFURANOSE AS PRECURSORS FOR THE SYNTHESIS OF L-PENTOFURANOSYL NUCLEOSIDES. In CARBOHYDRATE RESEARCH. ISSN 0008-6215, SEP 2 1991, vol. 216, p. 249-255.
    WITTY, D.R. - FLEET, G.W.J. - VOGT, K. - WILSON, F.X. - WANG, Y. - STORER, R. - MYERS, P.L. - WALLIS, C.J. RING CONTRACTION OF 2-O-TRIFLUOROMETHANESULFONATES OF ALPHA-HYDROXY-GAMMA-LACTONES TO OXETANE CARBOXYLIC ESTERS. In TETRAHEDRON LETTERS. ISSN 0040-4039, 1990, vol. 31, no. 33, p. 4787-4790.
    WITTY, D.R. - FLEET, G.W.J. - CHOI, S. - VOGT, K. - WILSON, F.X. - WANG, Y. - STORER, R. - MYERS, P.L. - WALLIS, C.J. RING CONTRACTION OF 3-DEOXY-2-O-TRIFLUOROMETHANESULFONATES OF ALPHA-HYDROXY-GAMMA-LACTONES TO OXETANES. In TETRAHEDRON LETTERS. ISSN 0040-4039, 1990, vol. 31, no. 47, p. 6927-6930.
    WU, J.C. - CHATTOPADHYAYA, J. NEW SYNTHESIS OF 2',3'-DIDEOXY-3'-C-CYANO-2'-SUBSTITUTED THYMIDINES BY MICHAEL ADDITION-REACTIONS. In TETRAHEDRON. ISSN 0040-4020, 1989, vol. 45, no. 3, p. 855-862.
    MARTIN, O.R. - RAO, S.P. - ELSHENAWY, H.A. - KURZ, K.G. - CUTLER, A.B. UNUSUAL 1,5-HYDRIDE SHIFTS IN LEWIS ACID MEDIATED REACTIONS OF BENZYLATED SUGARS - SYNTHESIS OF 3-ALKYLISOCHROMAN DERIVATIVES. In JOURNAL OF ORGANIC CHEMISTRY. ISSN 0022-3263, JUL 8 1988, vol. 53, no. 14, p. 3287-3292.
    WEISS, E. - DOBSON, M.E. - DASCH, G.A. BIOCHEMISTRY OF RICKETTSIAE - RECENT ADVANCES. In ACTA VIROLOGICA. ISSN 0001-723X, MAY 1987, vol. 31, no. 3, p. 271-286.
    WU, J.C. - BAZIN, H. - CHATTOPADHYAYA, J. REGIOSPECIFIC SYNTHESIS OF 2'-DEOXY-2',2''-DIDEUTERIO NUCLEOSIDES. In TETRAHEDRON. ISSN 0040-4020, 1987, vol. 43, no. 10, p. 2355-2368.
    CategoryADE
    Year1986
    Registered inWOS
    Registered inSCOPUS
    DOI 10.3891/acta.chem.scand.40b-0015
    article

    article

    rok vydaniarok metrikyIFIF Q (best)SJRSJR Q (best)
    1986
Number of the records: 1  

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