Expanding the diversity of unnatural cell-surface sialic acids

被引:116
作者
Luchansky, SJ
Goon, S
Bertozzi, CR [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Dept Mol & Cell Biol, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Howard Hughes Med Inst, Berkeley, CA 94720 USA
[4] Univ Calif Berkeley, Lawrence Berkeley Lab, Div Mat Sci, Berkeley, CA 94720 USA
关键词
azides; glycans; glycoconjugates; ketones; oligosaccharides; sialic acid; Staudinger ligation;
D O I
10.1002/cbic.200300789
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Introduction of sialic acid analogues to cells, rather than their upstream N-acetylmannosamine (ManNAc) precursors, improves the delivery of bioorthogonal functional groups to the cell surface and enables the incorporation of photoactivatable azides into glycoconjugates (see scheme).
引用
收藏
页码:371 / 374
页数:4
相关论文
共 14 条
[1]   Metabolic oligosaccharide engineering as a tool for glycobiology [J].
Dube, DH ;
Bertozzi, CR .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (05) :616-625
[2]   A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation [J].
Hang, HC ;
Yu, C ;
Kato, DL ;
Bertozzi, CR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2003, 100 (25) :14846-14851
[3]   Ketone isosteres of 2-N-acetamidosugars as substrates for metabolic cell surface engineering [J].
Hang, HC ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1242-1243
[4]   Metabolic labeling of glycoproteins with chemical tags through unnatural sialic acid biosynthesis [J].
Jacobs, CL ;
Yarema, KJ ;
Mahal, LK ;
Nauman, DA ;
Charters, NW ;
Bertozzi, CR .
APPLICATIONS OF CHIMERIC GENES AND HYBRID PROTEINS PT B, 2000, 327 :260-275
[5]   Substrate specificity of the sialic acid biosynthetic pathway [J].
Jacobs, CL ;
Goon, S ;
Yarema, KJ ;
Hinderlich, S ;
Hang, HC ;
Chai, DH ;
Bertozzi, CR .
BIOCHEMISTRY, 2001, 40 (43) :12864-12874
[6]   Biochemical engineering of the N-acyl side chain of sialic acid:: biological implications [J].
Keppler, OT ;
Horstkorte, R ;
Pawlita, M ;
Schmidts, C ;
Reutter, W .
GLYCOBIOLOGY, 2001, 11 (02) :11R-18R
[7]   OVERPRODUCTION OF CMP-SIALIC ACID SYNTHETASE FOR ORGANIC-SYNTHESIS [J].
LIU, JLC ;
SHEN, GJ ;
ICHIKAWA, Y ;
RUTAN, JF ;
ZAPATA, G ;
VANN, WF ;
WONG, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (10) :3901-3910
[8]   Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis [J].
Mahal, LK ;
Yarema, KJ ;
Bertozzi, CR .
SCIENCE, 1997, 276 (5315) :1125-1128
[9]   Versatile biosynthetic engineering of sialic acid in living cells using synthetic sialic acid analogues [J].
Oetke, C ;
Brossmer, R ;
Mantey, LR ;
Hinderlich, S ;
Isecke, R ;
Reutter, W ;
Keppler, OT ;
Pawlita, M .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (08) :6688-6695
[10]   DISACCHARIDE UPTAKE AND PRIMING IN ANIMAL-CELLS - INHIBITION OF SIALYL-LEWIS-X BY ACETYLATED GAL-BETA-1-]4GLCNAC-BETA-O-NAPHTHALENEMETHANOL [J].
SARKAR, AK ;
FRITZ, TA ;
TAYLOR, WH ;
ESKO, JD .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (08) :3323-3327