First O-Glycosylation of hydroxamic acids

被引：36
|
作者：
Thomas, Mickael
Gesson, Jean-Pierre
Papot, Sebastien
机构：
[1] Univ Poitiers, UMR 6514, F-86022 Poitiers, France
[2] CNRS, F-86022 Poitiers, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 11期
关键词：
D O I：
10.1021/jo0701839
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 angstrom molecular sieves in dichloromethane. Under such conditions, a wide range of new glycosyl donors including glucosyl, galactosyl, mannosyl, glucuronyl, and ribosyl hydroxamates were prepared in good to high yields. This procedure appears to be an advantageous alternative for the synthesis of glycosyl hydroxamates of biological interest.
引用
收藏
页码：4262 / 4264
页数：3
相关论文
共 50 条
  • [31] THE INFLUENCE OF FLANKING SEQUENCES ON O-GLYCOSYLATION
    OCONNELL, B
    TABAK, LA
    RAMASUBBU, N
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1991, 180 (02) : 1024 - 1030
  • [32] Editorial overview: Carbohydrates: O-glycosylation
    Wells, Lance
    Feizi, Ten
    CURRENT OPINION IN STRUCTURAL BIOLOGY, 2019, 56 : III - V
  • [33] A first look at the N- and O-glycosylation landscape in anuran skin secretions
    Barbosa, Eder Alves
    Costa Alves, Gabriel Sergio
    Andrade Coura, Marcelo de Melo
    de Lima e Silva, Higor
    da Rocha, Filipe Souza
    Nunes, Joao Bueno
    Watanabe, Matheus de Souza
    Andrade, Alan Carvalho
    Brand, Guilherme Dotto
    BIOCHIMIE, 2022, 197 : 19 - 37
  • [34] O-glycosylation of the cardiac IKs complex
    Chandrasekhar, Kshama D.
    Lvov, Anatoli
    Terrenoire, Cecile
    Gao, Grace Y.
    Kass, Robert S.
    Kobertz, William R.
    JOURNAL OF PHYSIOLOGY-LONDON, 2011, 589 (15): : 3721 - 3730
  • [35] Base-Promoted Glycosylation Allows Protecting Group-Free and Stereoselective O-Glycosylation of Carboxylic Acids
    Zuo, Hao
    Zhang, Chen
    Zhang, Yang
    Niu, Dawen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (42)
  • [36] TEMPORAL ASPECTS OF N-GLYCOSYLATION AND O-GLYCOSYLATION OF LEUKOSIALIN
    PILLERMICHEL, V
    PILLER, F
    KLIER, G
    FUKUDA, M
    FASEB JOURNAL, 1988, 2 (04): : A542 - A542
  • [37] Database analysis of O-glycosylation sites in proteins
    Christlet, THT
    Veluraja, K
    BIOPHYSICAL JOURNAL, 2001, 80 (02) : 952 - 960
  • [38] Mucin-Type O-Glycosylation in Invertebrates
    Staudacher, Erika
    MOLECULES, 2015, 20 (06): : 10622 - 10640
  • [39] Significant Roles of Notch O-Glycosylation in Cancer
    Wang, Weiwei
    Okajima, Tetsuya
    Takeuchi, Hideyuki
    MOLECULES, 2022, 27 (06):
  • [40] O-glycosylation of serum IgD in IgA nephropathy
    Smith, Alice C.
    de Wolff, Jacob F.
    Molyneux, Karen
    Feehally, John
    Barratt, Jonathan
    JOURNAL OF THE AMERICAN SOCIETY OF NEPHROLOGY, 2006, 17 (04): : 1192 - 1199
12345