Literature DB >> 3594476

Synthesis of the optically active 4-O-phosphono-D-glucosamine derivatives related to the nonreducing-sugar subunit of bacterial lipid A.

M Kiso, S Tanaka, M Fujita, Y Fujishima, Y Ogawa, H Ishida, A Hasegawa.   

Abstract

The optically active lipid A-subunit homologs named GLA-46, GLA-47, GLA-59, and GLA-60 have been synthesized stepwise by successive acylation at N-2 and O-3 of benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside with the 3-9O-(benzyloxy)methyl or 39O-tetradecanoyl derivative of optically active 3-hydroxytetradecanoic acid, and phosphorylation at O-4 of the D-glucosamine residue.

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Year:  1987        PMID： 3594476     DOI： 10.1016/0008-6215(87)80207-0

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  10 in total

1.  Immunopharmacological activities of 2-keto-3-deoxyoctonic acid-(alpha 2----6)-linked 4-O-phosphono-D-glucosamine derivatives carrying N- and 3-O-acyl substituents.

Authors:  Y Kumazawa; M Matsuura; J Y Homma; T Furuya; H Takimoto; K Inagaki; T Nagumo; M Kiso; A Hasegawa
Journal:  Infect Immun       Date:  1989-06       Impact factor: 3.441

2.  Activity of monosaccharide lipid A analogues in human monocytic cells as agonists or antagonists of bacterial lipopolysaccharide.

Authors:  M Matsuura; M Kiso; A Hasegawa
Journal:  Infect Immun       Date:  1999-12       Impact factor: 3.441

3.  Antimetastatic effect of endogenous tumor necrosis factor induced by the treatment of recombinant interferon gamma followed by an analogue (GLA-60) to synthetic lipid A subunit.

Authors:  I Saiki; H Maeda; J Murata; N Yamamoto; M Kiso; A Hasegawa; I Azuma
Journal:  Cancer Immunol Immunother       Date:  1989       Impact factor: 6.968

Review 4.  Modulating LPS signal transduction at the LPS receptor complex with synthetic Lipid A analogues.

Authors:  Aileen F B White; Alexei V Demchenko
Journal:  Adv Carbohydr Chem Biochem       Date:  2014       Impact factor: 12.200

5.  Relationship of structure and biological activity of monosaccharide lipid A analogues to induction of nitric oxide production by murine macrophage RAW264.7 cells.

Authors:  K Funatogawa; M Matsuura; M Nakano; M Kiso; A Hasegawa
Journal:  Infect Immun       Date:  1998-12       Impact factor: 3.441

6.  Cell activation by monosaccharide lipid A analogues utilizing Toll-like receptor 4.

Authors:  Riyoko Tamai; Yasuyuki Asai; Masahito Hashimoto; Koichi Fukase; Shoichi Kusumoto; Hideharu Ishida; Makoto Kiso; Tomohiko Ogawa
Journal:  Immunology       Date:  2003-09       Impact factor: 7.397

7.  Induction of an endogenous tumor necrosis factor in mice by murine recombinant interferon-gamma combined with a lipid A subunit analog (GLA-60) of low toxicity.

Authors:  I Saiki; H Maeda; T Sakurai; J Murata; J Iida; M Kiso; A Hasegawa; I Azuma
Journal:  Cancer Immunol Immunother       Date:  1989       Impact factor: 6.968

8.  Biophysical characterization of triacyl monosaccharide lipid a partial structures in relation to bioactivity.

Authors:  Klaus Brandenburg; Motohiro Matsuura; Holger Heine; Mareike Müller; Makato Kiso; Hideharu Ishida; Michel H J Koch; Ulrich Seydel
Journal:  Biophys J       Date:  2002-07       Impact factor: 4.033

9.  Importance of fatty acid substituents of chemically synthesized lipid A-subunit analogs in the expression of immunopharmacological activity.

Authors:  Y Kumazawa; M Nakatsuka; H Takimoto; T Furuya; T Nagumo; A Yamamoto; Y Homma; K Inada; M Yoshida; M Kiso
Journal:  Infect Immun       Date:  1988-01       Impact factor: 3.441

10.  DT-5461, a new synthetic lipid A analogue, inhibits lung and liver metastasis of tumor in mice.

Authors:  K Sato; I Saiki; Y C Yoo; Y Igarashi; M Kiso; A Hasegawa; I Azuma
Journal:  Jpn J Cancer Res       Date:  1992-10
  10 in total

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