Literature DB >> 10815986

Synthesis of glycosylated human interleukin-1alpha, neoglyco IL-1alpha, coupled with N-acetylneuraminic acid.

T Chiba1, K Moriya, S Nabeshima, H Hayashi, Y Kobayashi, S Sasayama, K Onozaki.   

Abstract

In order to develop glycosylated cytokine, recombinant human IL-1alpha was chemically modified with N-acetylneuraminic acid (NANA). NANA with C9 spacer, 8-(hydrazinocarbonyl)octyl 5-acetamido-3, 5-dideoxy-D-glycero-alpha-D-galacto-2-nonulo-pyranosidonic acid potassium salt (6), was synthesized by glycosylation of C9 spacer, 8-[2-N-(benzyloxycarbonyl)hydrazinocarbonyl]octanol, with methylthio glycoside derivatives of NANA in the presence of molecular sieves 3A and methyl (methylthio)sulfonium trifrate in propionitrile, followed by separation of a and beta anomers with a column chromatography and deprotection. Compound 6 was coupled to IL-1alpha by the acyl azide method. The glycosylated IL-1 was purified by anion-exchange chromatography, and NANA coupled to IL-1 was confirmed by oxidation with NaIO4. Based on the molecular weight average number of carbohydrate molecules introduced per molecule of IL-1alpha was estimated to be 2.9.

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Year:  1999        PMID： 10815986     DOI： 10.1023/a:1007017920392

Source DB:  PubMed          Journal:  Glycoconj J        ISSN： 0282-0080            Impact factor:   2.916


  20 in total

1.  Quantitative hydrolysis of thioglycosides.

Authors:  M J Krantz; Y C Lee
Journal:  Anal Biochem       Date:  1976-03       Impact factor: 3.365

2.  Binding of activated macrophages to tumor cells through a macrophage lectin and its role in macrophage tumoricidal activity.

Authors:  S Oda; M Sato; S Toyoshima; T Osawa
Journal:  J Biochem       Date:  1989-06       Impact factor: 3.387

3.  Cleavage of structural proteins during the assembly of the head of bacteriophage T4.

Authors:  U K Laemmli
Journal:  Nature       Date:  1970-08-15       Impact factor: 49.962

4.  The binding of d-glucosyl-neoglycoproteins to the hepatic asialoglycoprotein receptor.

Authors:  C P Stowell; Y C Lee
Journal:  J Biol Chem       Date:  1978-09-10       Impact factor: 5.157

5.  D-mannose dimer introduced human recombinant interleukin- 1 alpha, NEO IL-1 alpha, exhibits altered tissue distribution in mice.

Authors:  Y Takei; T Chiba; S Nabeshima; M Naruoka; K Wada; K Onozaki
Journal:  J Interferon Cytokine Res       Date:  1996-04       Impact factor: 2.607

6.  Development of glycosylated human interleukin-1alpha, neoglyco IL-1alpha, by coupling with D-galactose monosaccharide: synthesis and purification.

Authors:  T Chiba; S Nabeshima; Y Takei; K Onozaki
Journal:  Glycoconj J       Date:  1998-01       Impact factor: 2.916

7.  Development of glycosylated human interleukin-1alpha, neoglyco IL-1alpha, coupled with D-galactose monosaccharide: biological activities in vivo.

Authors:  S Nabeshima; T Chiba; Y Takei; A Ono; K Moriya; K Onozaki
Journal:  Glycoconj J       Date:  1998-05       Impact factor: 2.916

8.  Glycosylated human recombinant interleukin-1 alpha, neo interleukin-1 alpha, with D-mannose dimer exhibits selective activities in vivo.

Authors:  Y Takei; T Chiba; K Wada; H Hayashi; M Yamada; J Kuwashima; K Onozaki
Journal:  J Interferon Cytokine Res       Date:  1995-08       Impact factor: 2.607

9.  Binding site of the rabbit liver lectin specific for galactose/N-acetylgalactosamine.

Authors:  R T Lee
Journal:  Biochemistry       Date:  1982-03-02       Impact factor: 3.162

Review 10.  Biologic basis for interleukin-1 in disease.

Authors:  C A Dinarello
Journal:  Blood       Date:  1996-03-15       Impact factor: 22.113
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  3 in total

1.  Synthesis and biological activities in vitro and in vivo of glycosylated human interleukin-1alpha, neoglyco IL-1alpha, coupled with N -acetylneuraminyl-galactose.

Authors:  Masaaki Ootsubo; Taku Chiba; Yutaka Kobayashi; Hidetoshi Hayashi; Akiko Hayashi; Kikuo Onozaki
Journal:  Glycoconj J       Date:  2004       Impact factor: 2.916

2.  N-acetylneuraminic acid coupled human recombinant TNFalpha exhibits enhanced anti-tumor activity against Meth-A fibrosarcoma and reduced toxicity.

Authors:  Akiko Hayashi; Hidetoshi Hayashi; Taku Chiba; Satoshi Sasayama; Kikuo Onozaki
Journal:  Cancer Immunol Immunother       Date:  2006-10-10       Impact factor: 6.968

3.  Glycosylated human interleukin-1alpha, neoglyco IL-1alpha, coupled with N-acetylneuraminic acid exhibits selective activities in vivo and altered tissue distribution.

Authors:  S Sasayama; K Moriya; T Chiba; T Matsumura; H Hayashi; A Hayashi; K Onozaki
Journal:  Glycoconj J       Date:  2000-06       Impact factor: 2.916
  3 in total

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