Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

被引:4
作者
Krenek, Karel [1 ]
Simon, Petr [1 ]
Weignerova, Lenka [1 ]
Fliedrova, Barbora [1 ,2 ]
Kuzma, Marek [1 ]
Kren, Vladimir [1 ]
机构
[1] Acad Sci Czech Republic, Inst Microbiol, CZ-14220 Prague, Czech Republic
[2] Charles Univ Prague, Dept Biochem, CZ-12840 Prague, Czech Republic
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷
关键词
alpha-ManNAc; glycosidase; glycosylation; nitrophenyl; oxazoline; NKR-P1; ACTIVATION;
D O I
10.3762/bjoc.8.48
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio.
引用
收藏
页码:428 / 432
页数:5
相关论文
共 18 条
  • [1] RETRACTED: Improved preparation of β-D-ManNAc-(1→4)-D-Glc and β-D-TalNAc-(1→4)-D-Glc disaccharides and evaluation of their activating properties on the natural killer cells NKR-P1 and CD69 receptors (Retracted Article)
    Attolino, Emanuele
    Bonaccorsi, Filippo
    Catelani, Giorgio
    D'Andrea, Felicia
    Krenek, Karel
    Bezouska, Karel
    Kren, Vladimir
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 2008, 27 (03) : 156 - 171
  • [2] STUDY OF C-13H COUPLING-CONSTANTS IN HEXOPYRANOSES
    BOCK, K
    PEDERSEN, C
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03): : 293 - 299
  • [3] Synthesis of 2-acetamido-3-O-acetyl-2-deoxy-D-mannose phosphoramidites
    Freese, SJ
    Vann, WF
    [J]. CARBOHYDRATE RESEARCH, 1996, 281 (02) : 313 - 319
  • [4] GRAM-SCALE SYNTHESIS OF URIDINE 5'-DIPHOSPHO-N-ACETYLGLUCOSAMINE - COMPARISON OF ENZYMATIC AND CHEMICAL ROUTES
    HEIDLAS, JE
    LEES, WJ
    PALE, P
    WHITESIDES, GM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) : 146 - 151
  • [5] SOLID-PHASE SYNTHESIS OF GLYCOPEPTIDES - GLYCOSYLATION OF RESIN-BOUND SERINE-PEPTIDES BY 3,4,6-TRI-O-ACETYL-D-GLUCOSE-OXAZOLINE
    HOLLOSI, M
    KOLLAT, E
    LACZKO, I
    MEDZIHRADSZKY, KF
    THURIN, J
    OTVOS, L
    [J]. TETRAHEDRON LETTERS, 1991, 32 (12) : 1531 - 1534
  • [6] Synthesis of 4-nitrophenyl 2-acetamido-2-deoxy-β-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside
    Krist, P
    Kuzma, M
    Pelyvás, IF
    Simerská, P
    Kren, V
    [J]. COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2003, 68 (04) : 801 - 811
  • [7] RETRACTED: Toward an optimal oligosaccharide ligand for rat natural killer cell activation receptor NKR-P1 (Retracted Article)
    Krist, P
    Herkommerová-Rajnochová, E
    Rauvolfová, J
    Semenuk, T
    Vavrusková, P
    Pavlícek, J
    Bezouska, K
    Petrus, L
    Kren, V
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2001, 287 (01) : 11 - 20
  • [8] VIRULENCE, IMMUNITY, AND VACCINE RELATED TO STREPTOCOCCUS-PNEUMONIAE
    LEE, CJ
    BANKS, SD
    LI, JP
    [J]. CRITICAL REVIEWS IN MICROBIOLOGY, 1991, 18 (02) : 89 - 114
  • [9] LEE CJ, 1980, J BIOL CHEM, V255, P6847
  • [10] From polymer to size-defined oligomers: An expeditious route for the preparation of chondroitin oligosaccharides
    Lopin, C
    Jacquinet, JC
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) : 2574 - 2578