Methods for anomeric carbon-linked and fused sugar amino acid synthesis: The gateway to artificial glycopeptides

被引:301
作者
Dondoni, A [1 ]
Marra, A [1 ]
机构
[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
关键词
D O I
10.1021/cr9903003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Having solved over the last 30 years or so the majority of the problems associated with the stereocontrolled synthesis of natural O-oligosaccharides and O-glycoconjugates with a substantial beneficial effect on glycobiology, in recent times organic chemists have been focusing more interest upon the development of synthetic procedures for unnatural carbon-linked analogues. Various synthetic procedures to C-glycosyl amino acids have been developed to date.
引用
收藏
页码:4395 / +
页数:28
相关论文
共 145 条
  • [1] O-Glycosyl alpha-amino acids as building blocks for glycopeptide synthesis
    Arsequell, G
    Valencia, G
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (17) : 2839 - 2876
  • [2] Recent advances in the synthesis of complex N-glycopeptides
    Arsequell, G
    Valencia, G
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (16) : 3045 - 3094
  • [3] Remote asymmetric induction:: Synthesis of C-linked α-galactoserine and homoserine derivatives by electrophilic amination
    Arya, P
    Ben, RN
    Qin, HP
    [J]. TETRAHEDRON LETTERS, 1998, 39 (34) : 6131 - 6134
  • [4] DIASTEREOSELECTIVE RADICAL-ADDITION TO METHYLENEOXAZOLIDINONES - AN ENANTIOSELECTIVE ROUTE TO ALPHA-AMINO-ACIDS
    AXON, JR
    BECKWITH, ALJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (05) : 549 - 550
  • [5] ENANTIOSPECIFIC SYNTHESIS OF L-(3R AND 3S)-(BETA-D-RIBOFURANOSYL)-PYROGLUTAMIC ACIDS - POSSIBLE INTERMEDIATES IN C-NUCLEOSIDE BIOSYNTHESIS
    BALDWIN, JE
    ADLINGTON, RM
    ROBINSON, NG
    [J]. TETRAHEDRON LETTERS, 1988, 29 (03) : 375 - 378
  • [6] Beer T., 1995, BIOCHEMISTRY-US, V34, P11785
  • [7] SYNTHESIS OF CARBON-LINKED GLYCOPEPTIDES AS STABLE GLYCOPEPTIDE MODELS
    BERTOZZI, CR
    HOEPRICH, PD
    BEDNARSKI, MD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) : 6092 - 6094
  • [8] CARBON-LINKED GALACTOSPHINGOLIPID ANALOGS BIND SPECIFICALLY TO HIV-1 GP120
    BERTOZZI, CR
    COOK, DG
    KOBERTZ, WR
    GONZALEZSCARANO, F
    BEDNARSKI, MD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10639 - 10641
  • [9] POTENT INHIBITION OF GLYCOGEN-PHOSPHORYLASE BY A SPIROHYDANTOIN OF GLUCOPYRANOSE - FIRST PYRANOSE ANALOGS OF HYDANTOCIDIN
    BICHARD, CJF
    MITCHELL, EP
    WORMALD, MR
    WATSON, KA
    JOHNSON, LN
    ZOGRAPHOS, SE
    KOUTRA, DD
    OIKONOMAKOS, NG
    FLEET, GWJ
    [J]. TETRAHEDRON LETTERS, 1995, 36 (12) : 2145 - 2148
  • [10] SYNTHESIS OF GLYCOSYL ALPHA-AMINO-ACIDS
    BISCHOFBERGER, K
    HALL, RH
    JORDAAN, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (19) : 806 - 807