Synthesis of fluorine substituted oligosaccharide analogues of monoglucosylated glycan chain, a proposed ligand of lectin-chaperone calreticulin and calnexin

Yukishige Ito; Shinya Hagihara; Midori A. Arai; Ichiro Matsuo; Maki Takatani

doi:10.1023/B:GLYC.0000045109.60425.2e

Synthesis of fluorine substituted oligosaccharide analogues of monoglucosylated glycan chain, a proposed ligand of lectin-chaperone calreticulin and calnexin

Yukishige Ito, Shinya Hagihara, Midori A. Arai, Ichiro Matsuo, Maki Takatani

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

As a part of a exploring the N-glycan-mediated glycoprotein quality control in endoplasmic reticulum, 2-fluorinated derivative Glcα1 → 3Man(F) 1, Glcα1 → 3Man(F)α1 → 2Man2, and Glcα1 → 3Man(F)α1 → 2Manα1 → 2Man 3 were synthesized in a concise manner. These oligosaccharides were subjected to binding studies with calreticulin by using isothermal titration calorimetry. It was revealed that disaccharide 1 was a poor ligand, while tri- (2) and tetrasaccharide (3) had observable affinity.

Original language	English
Pages (from-to)	257-266
Number of pages	10
Journal	Glycoconjugate Journal
Volume	21
Issue number	5
DOIs	https://doi.org/10.1023/B:GLYC.0000045109.60425.2e
Publication status	Published - 2004
Externally published	Yes

Keywords

2-fluorinated oligosaccharide
calreticulin
glycoprotein quality control
synthesis

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Cell Biology

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10.1023/B:GLYC.0000045109.60425.2e

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Synthesis of fluorine substituted oligosaccharide analogues of monoglucosylated glycan chain, a proposed ligand of lectin-chaperone calreticulin and calnexin. / Ito, Yukishige; Hagihara, Shinya; Arai, Midori A.; Matsuo, Ichiro; Takatani, Maki.

In: Glycoconjugate Journal, Vol. 21, No. 5, 2004, p. 257-266.

Research output: Contribution to journal › Article › peer-review

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title = "Synthesis of fluorine substituted oligosaccharide analogues of monoglucosylated glycan chain, a proposed ligand of lectin-chaperone calreticulin and calnexin",

abstract = "As a part of a exploring the N-glycan-mediated glycoprotein quality control in endoplasmic reticulum, 2-fluorinated derivative Glcα1 → 3Man(F) 1, Glcα1 → 3Man(F)α1 → 2Man2, and Glcα1 → 3Man(F)α1 → 2Manα1 → 2Man 3 were synthesized in a concise manner. These oligosaccharides were subjected to binding studies with calreticulin by using isothermal titration calorimetry. It was revealed that disaccharide 1 was a poor ligand, while tri- (2) and tetrasaccharide (3) had observable affinity.",

keywords = "2-fluorinated oligosaccharide, calreticulin, glycoprotein quality control, synthesis",

author = "Yukishige Ito and Shinya Hagihara and Arai, {Midori A.} and Ichiro Matsuo and Maki Takatani",

note = "Funding Information: We thank Dr. Teiji Chihara and his staff for elemental analyses. Prof. Shunji Natori for providing GST-CRT construct and Ms. Akemi Takahashi for her technical assistance. This work was partially supported by Japan Society for the Promotion of Science [Grant-in-Aid for Scientific Research (B) (No. 16390011), and for Encouragement of Young Scientists (No. 15780220)].",

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doi = "10.1023/B:GLYC.0000045109.60425.2e",

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T1 - Synthesis of fluorine substituted oligosaccharide analogues of monoglucosylated glycan chain, a proposed ligand of lectin-chaperone calreticulin and calnexin

AU - Ito, Yukishige

AU - Hagihara, Shinya

AU - Arai, Midori A.

AU - Matsuo, Ichiro

AU - Takatani, Maki

N1 - Funding Information: We thank Dr. Teiji Chihara and his staff for elemental analyses. Prof. Shunji Natori for providing GST-CRT construct and Ms. Akemi Takahashi for her technical assistance. This work was partially supported by Japan Society for the Promotion of Science [Grant-in-Aid for Scientific Research (B) (No. 16390011), and for Encouragement of Young Scientists (No. 15780220)].

PY - 2004

Y1 - 2004

N2 - As a part of a exploring the N-glycan-mediated glycoprotein quality control in endoplasmic reticulum, 2-fluorinated derivative Glcα1 → 3Man(F) 1, Glcα1 → 3Man(F)α1 → 2Man2, and Glcα1 → 3Man(F)α1 → 2Manα1 → 2Man 3 were synthesized in a concise manner. These oligosaccharides were subjected to binding studies with calreticulin by using isothermal titration calorimetry. It was revealed that disaccharide 1 was a poor ligand, while tri- (2) and tetrasaccharide (3) had observable affinity.

AB - As a part of a exploring the N-glycan-mediated glycoprotein quality control in endoplasmic reticulum, 2-fluorinated derivative Glcα1 → 3Man(F) 1, Glcα1 → 3Man(F)α1 → 2Man2, and Glcα1 → 3Man(F)α1 → 2Manα1 → 2Man 3 were synthesized in a concise manner. These oligosaccharides were subjected to binding studies with calreticulin by using isothermal titration calorimetry. It was revealed that disaccharide 1 was a poor ligand, while tri- (2) and tetrasaccharide (3) had observable affinity.

KW - 2-fluorinated oligosaccharide

KW - calreticulin

KW - glycoprotein quality control

KW - synthesis

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VL - 21

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Synthesis of fluorine substituted oligosaccharide analogues of monoglucosylated glycan chain, a proposed ligand of lectin-chaperone calreticulin and calnexin

Abstract

Keywords

ASJC Scopus subject areas

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