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
  • [41] Recent developments in the enzymatic O-glycosylation of flavonoids
    Bernd Hofer
    Applied Microbiology and Biotechnology, 2016, 100 : 4269 - 4281
  • [42] O-glycosylation of cysteine-knot motifs
    Haltiwanger, Robert S.
    Dlugosz, Malgosia
    Luo, Yi
    Luther, Kelvin
    Nita-Lazar, Aleksandra
    Rana, Nadia
    Takeuchi, Hideyuki
    Holdener, Bernadette C.
    GLYCOBIOLOGY, 2006, 16 (11) : 1107 - 1108
  • [43] Pleiotropic effects of O-glycosylation in colon cancer
    Zhang, Liping
    Ten Hagen, Kelly G.
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2018, 293 (04) : 1315 - 1316
  • [44] N- and O-Glycosylation in the Murine Synaptosome
    Trinidad, Jonathan C.
    Schoepfer, Ralf
    Burlingame, Alma L.
    Medzihradszky, Katalin F.
    MOLECULAR & CELLULAR PROTEOMICS, 2013, 12 (12) : 3474 - 3488
  • [45] Morphology of Biomaterials Affect O-Glycosylation of HUVECs
    Hu, Xingyou
    Sheng, Jiaoyue
    Guan, Guoping
    Ju, Tongzhong
    Smith, David F. F.
    Wang, Lu
    JOURNAL OF FUNCTIONAL BIOMATERIALS, 2022, 13 (04)
  • [46] Global Mapping of O-Glycosylation of Human Herpesviruses
    Bagdonaite, Ieva
    Norden, Rickard
    Joshi, Hiren J.
    King, Sarah L.
    Vakhrushev, Sergey Y.
    Olofsson, Sigvard
    Wandall, Hans H.
    GLYCOBIOLOGY, 2016, 26 (12) : 1408 - 1408
  • [47] Differential O-glycosylation in cortical and medullary thymocytes
    Alvarez, Georgina
    Lascurain, Ricardo
    Hernandez-Cruz, Pedro
    Tetaert, Daniel
    Degand, Pierre
    Gorocica, Patricia
    Espinosa, Blanca
    Zenteno, Edgar
    Chavez, Raul
    BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2006, 1760 (08): : 1235 - 1240
  • [48] ALTERED O-GLYCOSYLATION OF PROTEINS IN THE NEOPLASTIC TROPHOBLAST
    COLE, LA
    JOURNAL OF CELLULAR BIOCHEMISTRY, 1987, : 158 - 158
  • [49] On surface O-glycosylation by catalytic microcontact printing
    Buhl, Moritz
    Traboni, Serena
    Koersgen, Martin
    Lamping, Sebastian
    Arlinghaus, Heinrich F.
    Ravoo, Bart Jan
    CHEMICAL COMMUNICATIONS, 2017, 53 (46) : 6203 - 6206
  • [50] Photoredox catalytic o-glycosylation with selenoglycoside donors
    Ragains, Justin R.
    Spell, Mark
    Wang, Xiaoping
    Wahba, Amir E.
    Conner, Elizabeth
    Fernando, Ranelka G.
    Stanley, George G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247