Collect. Czech. Chem. Commun. 1998, 63, 577-589
https://doi.org/10.1135/cccc19980577

New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity

Miroslav Ledvinaa, Daniel Zykab, Jan Ježeka, Tomáš Trnkab and David Šamana

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10, Prague 6, Czech Republic
b Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic

Individual author index pages


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    2003, Vol. 68, Issue 5, pp. 917–930 [Abstract]
  • Jiří Kroutil*, Jindřich Karban, Tomáš Trnka, Miloš Buděšínský and Miloslav Černý
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    2002, Vol. 67, Issue 12, pp. 1805–1819 [Abstract]
  • Jindřich Karban*, Miloš Buděšínský, Miloslav Černý and Tomáš Trnka
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  • Petr Bartoš, Miloslav Černý*, Iva Tišlerová and Tomáš Trnka
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    2000, Vol. 65, Issue 11, pp. 1737–1744 [Abstract]
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    2000, Vol. 65, Issue 11, pp. 1726–1736 [Abstract]
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    2000, Vol. 65, Issue 4, pp. 511–523 [Abstract]
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    1999, Vol. 64, Issue 4, pp. 673–684 [Abstract]
  • Irena G. Stará*, Ivo Starý*, Adrian Kollárovič, Filip Teplý, David Šaman and Pavel Fiedler
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    1999, Vol. 64, Issue 4, pp. 649–672 [Abstract]
  • Michal Hoskovec, Oldřich Hovorka, Blanka Kalinová, Bohumír Koutek, Aleš Svatoš, David Šaman, Kamil Vlček and Jan Vrkoč
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    1998, Vol. 63, Issue 7, pp. 1031–1044 [Abstract]
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    1998, Vol. 63, Issue 6, pp. 813–825 [Abstract]
  • Miroslav Ledvina, Jan Ježek, David Šaman and Věra Hříbalová
    Synthesis and Immunomodulating Activity of Lipophilic Analogs of N-Acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine
    1998, Vol. 63, Issue 4, pp. 590–598 [Abstract]
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    Efficient Stereoselective Synthesis of All Geometrical Isomers of Heptadeca-11,13-dienes
    1997, Vol. 62, Issue 9, pp. 1457–1467 [Abstract]
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    1997, Vol. 62, Issue 4, pp. 665–671 [Abstract]
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    1996, Vol. 61, Special Issue, pp. S23–S25 [Abstract]
  • Miloslav Černý, Tomáš Trnka and Miloš Buděšínský
    Preparation and Reactions of 2-Chloroethyl 1-Thio-β-D-glycopyranosides Derived from D-Galactose, D-Glucose, and 2-Acetamido-2-deoxy-D-glucose
    1996, Vol. 61, Issue 10, pp. 1489–1500 [Abstract]
  • Hana Chodounská, Alexander Kasal, David Šaman and Karel Ubik
    One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone
    1996, Vol. 61, Issue 7, pp. 1037–1046 [Abstract]
  • Martin Rejzek, Marie Zarevúcka, Zdeněk Wimmer, Tomáš Vaněk, Richard Tykva, Jelena Kuldová, David Šaman and Blanka Bennettová
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    1996, Vol. 61, Issue 4, pp. 605–614 [Abstract]
  • Luboš Arnold, Martina Pressová, David Šaman, Martin Vogtherr and Stefan Limmer
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    1996, Vol. 61, Issue 3, pp. 389–403 [Abstract]
  • Jan Ježek, Vlasta Velková, Václav Kašička, Zdeněk Prusík, Karel Ubik, Klaudie Bartová and Michael Mareš
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    1995, Vol. 60, Issue 6, pp. 1042–1049 [Abstract]
  • Miloš Buděšínský, Miloslav Černý, Ivan Černý, Stanislav Sámek and Tomáš Trnka
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    1994, Vol. 59, Issue 8, pp. 1841–1852 [Abstract]
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    1994, Vol. 59, Issue 5, pp. 1175–1202 [Abstract]
  • Jan Ježek and Richard A. Houghten
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    1994, Vol. 59, Issue 3, pp. 691–706 [Abstract]
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    Structure of 5-azacytosine nucleosides in acid solutions
    1993, Vol. 58, Special Issue, pp. S26–S28 [Abstract]
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    1993, Vol. 58, Issue 4, pp. 909–917 [Abstract]
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    1992, Vol. 57, Issue 11, pp. 2337–2358 [Abstract]
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    1991, Vol. 56, Issue 4, pp. 905–915 [Abstract]
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    1990, Vol. 55, Issue 11, pp. 2731–2737 [Abstract]
  • Michal Hoskovec, David Šaman and Bohumír Koutek
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    1990, Vol. 55, Issue 9, pp. 2270–2281 [Abstract]
  • Sergazy M. Adekenov, Miloš Buděšínský, Metram A. Abdikalikov, Coblandy M. Turdybekov, David Šaman, Ełżbieta Błoszyk, Bohdan Drożdż and Miroslav Holub
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    1990, Vol. 55, Issue 6, pp. 1568–1579 [Abstract]
  • Ludvík Streinz, David Šaman, Karel Konečný and Miroslav Romaňuk
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    1990, Vol. 55, Issue 6, pp. 1555–1561 [Abstract]
  • Jan Ježek, Evgenii A. Makarov, Tamara A. Balashova, Miloš Buděšínský, Tatyana M. Andronova and Vadim T. Ivanov
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    1990, Vol. 55, Issue 5, pp. 1326–1335 [Abstract]
  • Eva Körblová, Bohumír Koutek, David Šaman, Aleš Svatoš, Petr Maloň and Miroslav Romaňuk
    Synthesis of optically active 1-(2-furyl)-3-pentanol. A simple route to (2S, 5R/S)-chalcogran
    1990, Vol. 55, Issue 5, pp. 1234–1242 [Abstract]
  • Milan Souček, Ján Urban and David Šaman
    Preparation of N-protected α-amino alcohols by acetoxyborohydride reduction of N-protected α-amino acid esters
    1990, Vol. 55, Issue 3, pp. 761–765 [Abstract]
  • Aleš Svatoš, Irena Valterová, David Šaman and Jan Vrkoč
    Direct esterification of 2-methoxy-2-phenyl-3,3,3-trifluoropropionic acid: A reinvestigation
    1990, Vol. 55, Issue 2, pp. 485–490 [Abstract]
  • Miroslav Ledvina, Jiří Farkaš, Jaroslav Zajíček, Jan Ježek and Milan Zaoral
    An alternative synthesis of O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-α-aminobutanoyl-D-isoglutamine
    1989, Vol. 54, Issue 10, pp. 2784–2794 [Abstract]
  • Vladimír Král, Ladislav Jelínek and David Šaman
    Preparation and synthetic utilization of diarylmethylenemalonaldehydes
    1989, Vol. 54, Issue 10, pp. 2721–2730 [Abstract]
  • Miloš Buděšínský, Halina Grabarczyk, Włodzimierz M. Daniewski, Andrzej Wawrzuń, Maria Gulumka, David Šaman, Bohdan Drożdż and Miroslav Holub
    Sesquiterpene lactones from Venidium hirsutum BEROL. species
    1989, Vol. 54, Issue 7, pp. 1919–1927 [Abstract]
  • Jan Ježek, Ivo Bláha, Milan Zaoral, Eva Hamšíková, Hana Závadová and Vladimír Vonka
    Synthetic segments of influenza virus haemagglutinins
    1989, Vol. 54, Issue 2, pp. 516–522 [Abstract]
  • Miloš Buděšínský, Le Viet Ngoc Phuong, Nestor Perez Souto, Włodzimierz M. Daniewski, Andrzej Wawrzuń, Maria Gumułka, Soňa Vašíčková, David Šaman, Bohdan Drożdż, Halina Grabarczyk, Urszula Rychłewska and Miroslav Holub
    Isolation and structures of sesquiterpene lactones: Aerial parts of Arctotis grandis THUNB. species
    1989, Vol. 54, Issue 2, pp. 473–486 [Abstract]
  • Miloš Buděšínský, David Šaman, Jan Pelnař, Soňa Vašíčková, Bohdan Drożdż, Halina Grabarczyk, Le Viet Ngoc Phuong and Miroslav Holub
    Arctolide-revision of its stereostructure and determination of absolute configuration. Detailed 1H and 13C NMR analysis
    1989, Vol. 54, Issue 1, pp. 166–188 [Abstract]
  • Jan Ježek, Milan Zaoral, Miloš Buděšínský, Jiří Günther and Jiří Rotta
    Muramyl-dipeptide analogues: Synthesis and biological activities
    1988, Vol. 53, Issue 11, pp. 2897–2906 [Abstract]
  • Stanislav Sámek, Tomáš Trnka and Miloslav Černý
    Reactivity of hydroxyl groups of 1,6 : 2,3- and 1,6 : 3,4-dianhydrido-β-D-hexapyranoses in methylation with iodomethane
    1988, Vol. 53, Issue 3, pp. 633–637 [Abstract]
  • Petr Holý, Martin Bělohradský, Ivan Stibor, Juraj Koudelka, David Šaman, Jana Hodačová, Antonín Holý and Jiří Závada
    Crown and azacrown ethers with pendant adenine group
    1987, Vol. 52, Issue 12, pp. 2971–2982 [Abstract]
  • Dalimil Dvořák, David Šaman, Miloš Buděšínský and Zdeněk Arnold
    Arbuzov rearrangement in the reaction of arylmethylenemalonaldehydes with trimethyl phosphite: Formation of 2-(α-dimethoxyphosphonylbenzyl)-3-methoxyacroleins
    1987, Vol. 52, Issue 12, pp. 2926–2935 [Abstract]
  • Dalimil Dvořák, David Šaman, Jana Hodačová, Vladimír Král and Zdeněk Arnold
    Michael reaction of methylenemalonaldehydes: Synthetic approach to 4H-pyran-5-carboxaldehydes and 2-amino-4H-pyran-5-carboxaldehydes
    1987, Vol. 52, Issue 11, pp. 2687–2698 [Abstract]
  • Ján Urban, Petr Kuzmič, David Šaman and Milan Souček
    Regioselectivity of nucleophilic aromatic photosubstitution in the biphenyl series. Photohydrolysis of some dimethoxynitrobiphenyls
    1987, Vol. 52, Issue 10, pp. 2482–2491 [Abstract]
  • Zdeněk Wimmer, Miloš Buděšínský, Tomáš Macek, Aleš Svatoš, David Šaman, Soňa Vašíčková and Miroslav Romaňuk
    Biotransformation of 2-(4-methoxybenzyl)-1-cyclohexanone by means of Saccharomyces cerevisiae
    1987, Vol. 52, Issue 9, pp. 2326–2337 [Abstract]
  • Jan Ježek, Radovan Straka, Viktor Krchňák, Miloš Ryba, Jiří Rotta, Peter Mayer and Milan Zaoral
    Synthesis of peptide and glycopeptide fragments of bacterial cell walls
    1987, Vol. 52, Issue 6, pp. 1609–1624 [Abstract]
  • Ivan Veselý, David Šaman and Ivan Stibor
    Ag(I) complexes of F2α prostaglandins
    1987, Vol. 52, Issue 6, pp. 1583–1588 [Abstract]
  • Stanislav Böhm, Renata Prantová, David Šaman, Petr Trška and Josef Kuthan
    Reaction of some nucleophiles with 2,6-di-tert-butylpyrylium perchlorate
    1987, Vol. 52, Issue 5, pp. 1305–1314 [Abstract]
  • Miloš Buděšínský and David Šaman
    Identification of acyl groups occurring in sesquiterpene lactones: Proton and carbon-13 NMR study
    1987, Vol. 52, Issue 2, pp. 453–475 [Abstract]
  • Jaroslav Kopecký, David Šaman and Ladislav Novotný
    Methylation of substituted 1,4-benzoquinones
    1987, Vol. 52, Issue 1, pp. 228–232 [Abstract]
  • Jaroslav Kopecký, David Šaman and Ladislav Novotný
    Methoxylation of substituted 1,4-benzoquinones
    1987, Vol. 52, Issue 1, pp. 223–227 [Abstract]
  • Ludvík Streinz, Irena Valterová, Zdeněk Wimmer, Miloš Buděšínský, David Šaman, Jitka Kohoutová, Miroslav Romaňuk and Jan Vrkoč
    Direct esterification of α-methoxy-α-(trifluoromethyl)phenylacetic acid
    1986, Vol. 51, Issue 10, pp. 2207–2213 [Abstract]
  • Zdenka Smítalová, Miloš Buděšínský, David Šaman and Miroslav Holub
    Minor sesquiterpenic lactones of Laser trilobum (L) BORKH. species
    1986, Vol. 51, Issue 6, pp. 1323–1339 [Abstract]
  • Miroslav Holub, Miloš Buděšínský, Zdenka Smítalová, David Šaman and Urszula Rychłewska
    Structure of isosilerolide, relative and absolute configuration of silerolide and lasolide - Sesquiterpenic lactones of new stereoisomeric type of eudesmanolides
    1986, Vol. 51, Issue 4, pp. 903–929 [Abstract]
  • Dalimil Dvořák, Miloš Buděšínský, David Šaman and Zdeněk Arnold
    Benzylidenemalonaldehydes: A redox reaction during the attempted cycloaddition on nitrosobenzene
    1985, Vol. 50, Issue 10, pp. 2260–2264 [Abstract]
  • Miroslav Holub, Miloš Buděšínský, Zdenka Smítalová, David Šaman and Urszula Rychłewska
    Structure of laserolide and isolaserolide: Revision of constitution and determination of relative and absolute configuration
    1985, Vol. 50, Issue 8, pp. 1878–1887 [Abstract]
  • Juraj Koudelka, David Šaman and Otto Exner
    Secondary steric effects in 2,4,6-trialkylated acetophenones and nitrobenzenes: Dipole moments and 13C NMR spectra
    1985, Vol. 50, Issue 1, pp. 208–214 [Abstract]
  • Wojciech Kroszczyṅski, Włodzimierz M. Daniewski, Miloš Buděšínský, David Šaman, Halina Grabarczyk, Bohdan Drożdż and Miroslav Holub
    Minor sesquiterpenic lactones from Ursinia anthemoides (L.) POIRET
    1985, Vol. 50, Issue 1, pp. 94–102 [Abstract]
  • Karel Konečný, Milan Streibl, Soňa Vašíčková, Miloš Buděšínský, David Šaman, Karel Ubik and Vlastimil Herout
    Constituents of the liverwort Bazzania trilobata of Czech origin
    1985, Vol. 50, Issue 1, pp. 80–93 [Abstract]
  • Jaroslav Kopecký, David Šaman, Tomáš Vaněk and Ladislav Novotný
    Components of the wood-rotting fungus Sarcodontia setosa
    1984, Vol. 49, Issue 7, pp. 1622–1626 [Abstract]
  • Miloš Buděšínský, Miroslav Holub, David Šaman, Zdenka Smítalová, Ayhan Ulubelen and Sevil Öksüz
    Structure of istanbulin A and istanbulin B - two sesquiterpenic lactones from Smyrnium olusatrum L.
    1984, Vol. 49, Issue 5, pp. 1311–1317 [Abstract]
  • Zdenka Smítalová, Miloš Buděšínský, David Šaman, Soňa Vašíčková and Miroslav Holub
    Components of the extract from the underground parts of Laserpitium siler L. of slovenian origin, mainly sesquiterpenic lactones
    1984, Vol. 49, Issue 4, pp. 852–870 [Abstract]
  • Miroslav Ledvina and Jiří Farkaš
    Alternative synthesis of 4-methyl-2H-1,2,6-thiadiazin-3(6H)-one 1,1-dioxide, a structural analogue of thymine
    1984, Vol. 49, Issue 4, pp. 840–851 [Abstract]
  • Miloš Buděšínský, David Šaman, Gerard Nowak, Bohdan Drożdż and Miroslav Holub
    9α-Hydroxyparthenolide from Zoegea baldschuanica C. WINKL. and its absolute configuration
    1984, Vol. 49, Issue 3, pp. 637–641 [Abstract]
  • Ivan Černý, Tomáš Trnka and Miloslav Černý
    Azido derivatives of 1,6-anhydro-β-D-hexopyranoses corresponding to 3-deoxy- and 4-deoxy-D-glucosamine
    1984, Vol. 49, Issue 2, pp. 433–443 [Abstract]
  • Miloslav Černý, Jitka Doležalová, Jindra Mácová, Josef Pacák, Tomáš Trnka and Miloš Buděšínský
    Preparation of 3-deoxy-3-fluoro-D-mannose and corresponding hexitol
    1983, Vol. 48, Issue 9, pp. 2693–2700 [Abstract]
  • Ivan Černý, Tomáš Trnka and Miloslav Černý
    Preparation of 2-amino-2,4-dideoxy-D-lyxo-hexopyranose (4-deoxy-D-mannosamine) from 1,6-anhydro-β-D-glucopyranose
    1983, Vol. 48, Issue 8, pp. 2386–2394 [Abstract]
  • Viktor Krchňák, Jan Ježek and Milan Zaoral
    Preparation of N-acetylnormuramyl-α-aminobutyryl-D-isoglutaminyl-lysyl-lysyl-lysine
    1983, Vol. 48, Issue 7, pp. 2079–2081 [Abstract]
  • Milan Zaoral, Jan Ježek and Jiří Rotta
    Preparation and some biological properties of N-acetylmuramyl-alanyl-D-isoglutamine (MDP) analogues
    1982, Vol. 47, Issue 11, pp. 2989–2995 [Abstract]
  • Miroslav Holub, Zdeněk Samek, Miloš Buděšínský, David Šaman, Ełżbieta Błoszyk and Bohdan Drożdż
    8α-Hydroxybalchanin - A new sesquiterpenic lactone from Leucanthemella serotina (L.) TZVEL.
    1982, Vol. 47, Issue 11, pp. 2927–2931 [Abstract]
  • Miloš Buděšínský, David Šaman and Zdeněk Wimmer
    Conformation studies of isomeric 1-acyloxy-2-(4-methoxybenzyl)-cyclohexanes by 1H NMR spectroscopy
    1982, Vol. 47, Issue 10, pp. 2763–2767 [Abstract]
  • Jitka Doležalová, Tomáš Trnka and Miloslav Černý
    Preparation of 1,6:3,4-dianhydro-β-D-altropyranose as starting substance for the synthesis of 3-substituted D-mannose derivatives
    1982, Vol. 47, Issue 9, pp. 2415–2422 [Abstract]
  • Miroslav Ledvina and Jiří Farkaš
    Synthesis of methyl 3-(N'-alkylureido)-2-methyl-2-propenoates and their cyclization to 3-alkyl-5-methyluracils
    1982, Vol. 47, Issue 2, pp. 676–688 [Abstract]
  • František Tureček, Tomáš Trnka and Miloslav Černý
    Fragmentation of isomeric dideoxy derivatives of 1,6-anhydro-β-D-hexopyranoses under electron impact
    1981, Vol. 46, Issue 10, pp. 2390–2403 [Abstract]
  • Milan Zaoral, Jan Ježek, Viktor Krchňák and Radovan Straka
    Synthesis of peptides, glyco derivatives and glycopeptides from bacterial cell walls
    1980, Vol. 45, Issue 5, pp. 1424–1446 [Abstract]
  • Miloš Buděšínský, Miloslav Černý, Tomáš Trnka and Soňa Vašíčková
    1H NMR spectra and the conformation of 1,6 : 2,3- and 1,6 : 3,4-dianhydro-β-D-hexopyranoses and their derivatives
    1979, Vol. 44, Issue 6, pp. 1965–1983 [Abstract]
  • Miloš Buděšínský, Tomáš Trnka and Miloslav Černý
    The 1H NMR spectra and the conformation of 1,6-anhydro-β-D-hexopyranoses and their triacetates
    1979, Vol. 44, Issue 6, pp. 1949–1964 [Abstract]
  • Milan Zaoral, Jan Ježek, Radovan Straka and Karel Mašek
    Glycopeptides of bacterial walls. A novel method of removal benzyl and benzylidene residues
    1978, Vol. 43, Issue 7, pp. 1797–1802 [Abstract]