Advances in the Biology and Chemistry of Sialic Acids

被引:463
作者
Chen, Xi [1 ]
Varki, Ajit [2 ,3 ]
机构
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
[2] Univ Calif San Diego, Dept Med, La Jolla, CA 92093 USA
[3] Univ Calif San Diego, Dept Cellular & Mol Med, Glycobiol Res & Training Ctr, La Jolla, CA 92093 USA
关键词
Biology; Carbohydrates; Chemistry; CMP-slalic acid synthetase; Glycan; Sialic acid; Siatic acid aldolase; Sialidase; Sialoside; Sialyltransferase; ENGINEERED ESCHERICHIA-COLI; N-ACETYLNEURAMINIC ACID; ALPHA/BETA-GALACTOSIDE ALPHA-2,3-SIALYLTRANSFERASE; PASTEURELLA-MULTOCIDA SIALYLTRANSFERASE; EFFICIENT CHEMOENZYMATIC SYNTHESIS; LARGE-SCALE PRODUCTION; CRUZI TRANS-SIALIDASE; GROUP-B STREPTOCOCCUS; ONE-POT SYNTHESIS; O-ACETYL GROUPS;
D O I
10.1021/cb900266r
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
Sialic acids are a subset of nonulosonic acids, which are nine-carbon alpha-keto aldonic acids. Natural existing sialic acid-containing structures are presented in different sialic acid forms, various sialyl, linkages, and on diverse underlying glycans. They play important roles in biological, pathological, and immunological processes. Sialobiology has been a challenging and yet attractive research area. Recent advances in chemical and chemoenzymatic synthesis, as well as large-scale E coli cell-based production, have provided a large library of sialo-side standards and derivatives in amounts sufficient for structure-activity relationship studies. Sialoglycan microarrays provide an efficient platform for quick identification of preferred ligands for sialic acid-binding proteins. Future research on sialic acid wilt continue to be at the Interface of chemistry and biology. Research efforts not only will lead to a better understanding of the biological and pathological importance of sialic acids and their diversity but also could lead to the development of therapeutics.
引用
收藏
页码:163 / 176
页数:14
相关论文
共 140 条
[61]   Structure-function analysis of the human sialyltransferase ST3Gal I -: Role of N-glycosylation and a novel conserved sialylmotif [J].
Jeanneau, C ;
Chazalet, V ;
Augé, C ;
Soumpasis, DM ;
Harduin-Lepers, A ;
Delannoy, P ;
Imberty, A ;
Breton, C .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (14) :13461-13468
[62]   Synthesis of oligosaccharides by bacterial enzymes [J].
Johnson, KF .
GLYCOCONJUGATE JOURNAL, 1999, 16 (02) :141-146
[63]   Haemophilus influenzae type b strain A2 has multiple sialyltransferases involved in lipooligosaccharide sialylation [J].
Jones, PA ;
Samuels, NM ;
Phillips, NJ ;
Munson, RS ;
Bozue, JA ;
Arseneau, JA ;
Nichols, WA ;
Zaleski, A ;
Gibson, BW ;
Apicella, MA .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (17) :14598-14611
[64]   Crystal structure of Vibrionaceae Photobacterium sp JT-ISH-224 α2,6-sialyltransferase in a ternary complex with donor product CMP and acceptor substrate lactose:: catalytic mechanism and substrate recognition [J].
Kakuta, Yoshimitsu ;
Okino, Nozomu ;
Kajiwara, Hitomi ;
Ichikawa, Masako ;
Takakura, Yoshimitsu ;
Ito, Makoto ;
Yamamoto, Takeshi .
GLYCOBIOLOGY, 2008, 18 (01) :66-73
[65]   MIGRATION OF O-ACETYL GROUPS IN N,O-ACETYLNEURAMINIC ACIDS [J].
KAMERLING, JP ;
SCHAUER, R ;
SHUKLA, AK ;
STOLL, S ;
VANHALBEEK, H ;
VLIEGENTHART, JFG .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1987, 162 (03) :601-607
[66]   Selectins and their ligands: Current concepts and controversies [J].
Kansas, GS .
BLOOD, 1996, 88 (09) :3259-3287
[67]   Human B-lymphocytes express α2-6-sialylated 6-sulfo-N-acetyllactosamine serving as a preferred ligand for CD22/Siglec-2 [J].
Kimura, Naoko ;
Ohmori, Katsuyuki ;
Miyazaki, Keiko ;
Izawa, Mineko ;
Matsuzaki, Yuji ;
Yasuda, Yosuke ;
Takematsu, Hiromu ;
Kozutsumi, Yasunori ;
Moriyama, Akihiko ;
Kannagi, Reiji .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, 282 (44) :32200-32207
[68]   Recent advances in the synthesis of sialic acid derivatives and sialylmimetics as biological probes [J].
Klefel, MJ ;
von Itzstein, M .
CHEMICAL REVIEWS, 2002, 102 (02) :471-490
[69]   5,7-diamino-3,5,7,9-tetradeoxynon-2-ulosonic acids in bacterial glycopolymers:: Chemistry and biochemistry [J].
Knirel, YA ;
Shashkov, AS ;
Tsvetkov, YE ;
Jansson, PE ;
Zähringer, U .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 58, 2003, 58 :371-417
[70]  
Komba S, 1999, ANGEW CHEM INT EDIT, V38, P1131, DOI 10.1002/(SICI)1521-3773(19990419)38:8<1131::AID-ANIE1131>3.0.CO