Preparation of asparagine-linked monoglucosylated high-mannose-type oligosaccharide from egg yolk

被引：16
作者：
Wang, Ning [1 ,2 ]
Seko, Akira [1 ]
Takeda, Yoichi [1 ]
Ito, Yukishige [1 ,2 ]
机构：
[1] Japan Sci & Technol Agcy JST, ERATO, Ito Glycotril Project, Wako, Saitama 3510198, Japan
[2] RIKEN, Synthet Cellular Chem Lab, Wako, Saitama 3510198, Japan
来源：
CARBOHYDRATE RESEARCH | 2015年 / 411卷
关键词：
Monoglucosylated high-mannose-type; oligosaccharide; Glycopeptide; Egg yolk; IgY; GLYCOPROTEIN QUALITY-CONTROL; GLYCOSYLATION; THERAPEUTICS; STRATEGY;
D O I：
10.1016/j.carres.2015.04.011
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Monoglucosylated high-mannose-type glycan (Glc(1)Man(9)GlcNAc(2): G1M9) is well-known as a key glycoform in the glycoprotein folding process, which is specifically recognized by lectin chaperones calnexin (CNX) and calreticulin (CRT) in the endoplasmic reticulum (ER). In this work, we developed an efficient method for the preparation of G1M9-Asn. The G1M9-Asn was obtained from the IgY-rich fraction derived from hen egg yolk by the digestion with pronase. The a-amino group of asparagine in G1M9-Asn was protected with the 9-fluorenylmethyloxycarbonyl (Fmoc) group and the labeled glycans were subsequently purified using high performance liquid chromatography (HPLC). This method will provide useful substrates for analysis of the glycoprotein folding cycle in the ER. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：37 / 41
页数：5
相关论文
共 18 条
  • [1] Design and synthesis of oligosaccharides that interfere with glycoprotein quality-control systems
    Arai, MA
    Matsuo, I
    Hagihara, S
    Totani, K
    Maruyama, J
    Kitamoto, K
    Ito, Y
    [J]. CHEMBIOCHEM, 2005, 6 (12) : 2281 - 2289
  • [2] Glycans in cancer and inflammation. Potential for therapeutics and diagnostics
    Dube, DH
    Bertozzi, CR
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2005, 4 (06) : 477 - 488
  • [3] A COLORIMETRIC METHOD FOR THE DETERMINATION OF SUGARS
    DUBOIS, M
    GILLES, K
    HAMILTON, JK
    REBERS, PA
    SMITH, F
    [J]. NATURE, 1951, 168 (4265) : 167 - 167
  • [4] Role of glycosylation indevelopment
    Haltiwanger, RS
    Lowe, JB
    [J]. ANNUAL REVIEW OF BIOCHEMISTRY, 2004, 73 : 491 - 537
  • [5] Glycomics Hits the Big Time
    Hart, Gerald W.
    Copeland, Ronald J.
    [J]. CELL, 2010, 143 (05) : 672 - 676
  • [6] CONFORMATIONAL TRANSITIONS IN N-LINKED OLIGOSACCHARIDES
    HOMANS, SW
    DWEK, RA
    BOYD, J
    MAHMOUDIAN, M
    RICHARDS, WG
    RADEMACHER, TW
    [J]. BIOCHEMISTRY, 1986, 25 (20) : 6342 - 6350
  • [7] Chemical Synthesis of Intentionally Misfolded Homogeneous Glycoprotein: A Unique Approach for the Study of Glycoprotein Quality Control
    Izumi, Masayuki
    Makimura, Yutaka
    Dedola, Simone
    Seko, Akira
    Kanamori, Akiko
    Sakono, Masafumi
    Ito, Yukishige
    Kajihara, Yasuhiro
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) : 7238 - 7241
  • [8] Glycosylation as a strategy to improve antibody-based therapeutics
    Jefferis, Roy
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2009, 8 (03) : 226 - 234
  • [9] Top-Down Chemoenzymatic Approach to a High-Mannose-Type Glycan Library: Synthesis of a Common Precursor and Its Enzymatic Trimming
    Koizumi, Akihiko
    Matsuo, Ichiro
    Takatani, Maki
    Seko, Akira
    Hachisu, Masakazu
    Takeda, Yoichi
    Ito, Yukishige
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) : 7426 - 7431
  • [10] AN EFFICIENT PREPARATION AND STRUCTURAL CHARACTERIZATION OF SIALYLGLYCOPEPTIDES FROM PROTEASE TREATED EGG-YOLK
    KOKETSU, M
    SEKO, A
    JUNEJA, LR
    KIM, M
    KASHIMURA, N
    YAMAMOTO, T
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (06) : 833 - 841
12