Facile synthesis of a glycopeptide building block of antifreeze glycoprotein

被引：0
|
作者：
Jiaang, WT [1 ]
Hsiao, KF
Chen, ST
Wang, KT
机构：
[1] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan
[2] Natl Taiwan Univ, Dept Chem, Taipei 111, Taiwan
来源：
SYNTHESIS-STUTTGART | 1999年 / 09期
关键词：
antifreeze; glycopeptides; solid phase synthesis; tetramethylurea; protecting groups; Moz;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new procedure for synthesizing a building block of antifreeze glycoprotein (AFGP) 1, Moz-Ala-(Gal beta 1--> 3GalNAc alpha 1)Thr-Ala-OH 7 has been developed. The onium salt is an important intermediate to generate alpha-glycopeptide 5 of excellent yield with high selectivity as a key step. One can successfully remove the Moz protective group of glycopeptide selectively with formic acid without cleaving the glycosidic bond.
引用
收藏
页码：1687 / 1690
页数：4
相关论文
共 50 条
  • [31] Evolution of an antifreeze glycoprotein
    Chi-Hing C. Cheng
    Liangbiao Chen
    Nature, 1999, 401 : 443 - 444
  • [32] Chemical synthesis of homogeneous antifreeze glycoprotein having uniform GalNAc modification and its antifreeze activity
    Okamoto, Ryo
    Orii, Ryo
    Izumi, Masayuki
    Fukami, Daichi
    Tsuda, Sakae
    Kajihara, Yasuhiro
    PROTEIN SCIENCE, 2016, 25 : 65 - 65
  • [33] Evolution of an antifreeze glycoprotein
    Cheng, CHC
    Chen, LB
    NATURE, 1999, 401 (6752) : 443 - 444
  • [34] Highly regioselective synthesis of a 3-O-sulfonated arabino Lewisa asparagine building block suitable for glycopeptide synthesis
    Roesch, Alexander
    Kunz, Horst
    CARBOHYDRATE RESEARCH, 2006, 341 (10) : 1597 - 1608
  • [35] Fully convergent solid phase synthesis of antifreeze glycoprotein analogues
    Eniade, A
    Ben, RN
    BIOMACROMOLECULES, 2001, 2 (02) : 557 - 561
  • [36] MELTING INHIBITION AND SUPERHEATING OF ICE BY AN ANTIFREEZE GLYCOPEPTIDE
    KNIGHT, CA
    DEVRIES, AL
    SCIENCE, 1989, 245 (4917) : 505 - 507
  • [37] Antifreeze glycoprotein analogs: Synthesis, in vitro testing and applications.
    Ben, RN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U255 - U255
  • [38] Vapour pressure of aqueous antifreeze glycopeptide solutions
    Westh, P
    Ramlov, H
    Wilson, PW
    DeVries, AL
    CRYO-LETTERS, 1997, 18 (05) : 277 - 282
  • [39] ADSORPTION TO ICE OF FISH ANTIFREEZE GLYCOPEPTIDE-7 AND GLYCOPEPTIDE-8
    KNIGHT, CA
    DRIGGERS, E
    DEVRIES, AL
    BIOPHYSICAL JOURNAL, 1993, 64 (01) : 252 - 259
  • [40] Synthesis and functionalization of magnetic nanoparticles for glycoprotein and glycopeptide enrichment: A review
    Austria Jr, Elmer S.
    Lamorena, Rheo B.
    Arco, Susan D.
    MICROCHEMICAL JOURNAL, 2024, 201
12345