Advances in the Biology and Chemistry of Sialic Acids

被引:455
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
  • [1] An effective sialylation method using N-Troc- and N-Fmoc-protected β-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen
    Adachi, M
    Tanaka, H
    Takahashi, T
    [J]. SYNLETT, 2004, (04) : 609 - 614
  • [2] Structural insights into the catalytic mechanism of Trypanosoma cruzi trans-sialidase
    Amaya, MF
    Watts, AG
    Damager, I
    Wehenkel, A
    Nguyen, T
    Buschiazzo, A
    Paris, G
    Frasch, AC
    Withers, SG
    Alzari, PM
    [J]. STRUCTURE, 2004, 12 (05) : 775 - 784
  • [3] 1,5-lactamized sialyl acceptors for various disialoside syntheses: Novel method for the synthesis of glycan portions of Hp-S6 and HLG-2 gangliosides
    Ando, H
    Koike, Y
    Koizumi, S
    Ishida, H
    Kiso, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (41) : 6759 - 6763
  • [4] Extending the possibility of an N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis
    Ando, H
    Koike, Y
    Ishida, H
    Kiso, M
    [J]. TETRAHEDRON LETTERS, 2003, 44 (36) : 6883 - 6886
  • [5] Chemical diversity in the sialic acids and related α-keto acids:: An evolutionary perspective
    Angata, T
    Varki, A
    [J]. CHEMICAL REVIEWS, 2002, 102 (02) : 439 - 469
  • [6] Large-scale in vivo synthesis of the carbohydrate moieties of gangliosides GM1 and GM2 by metabolically engineered Escherichia coli
    Antoine, T
    Priem, B
    Heyraud, A
    Greffe, L
    Gilbert, M
    Wakarchuk, BW
    Lam, JS
    Samain, E
    [J]. CHEMBIOCHEM, 2003, 4 (05) : 406 - 412
  • [7] Glycan array screening reveals a candidate ligand for Siglec-8
    Bochner, BS
    Alvarez, RA
    Mehta, P
    Bovin, NV
    Blixt, O
    White, JR
    Schnaar, RL
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (06) : 4307 - 4312
  • [8] Recent advances in O-sialylation
    Boons, GJ
    Demchenko, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (12) : 4539 - +
  • [9] Haemophilus ducreyi produces a novel sialyltransferase -: Identification of the sialyltransferase gene and construction of mutants deficient in the production of the sialic acid-containing glycoform of the lipooligosaccharide
    Bozue, JA
    Tullius, MV
    Wang, J
    Gibson, BW
    Munson, RS
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (07) : 4106 - 4114
  • [10] Structures and mechanisms of glycosyltransferases
    Breton, C
    Snajdrová, L
    Jeanneau, C
    Koca, J
    Imberty, A
    [J]. GLYCOBIOLOGY, 2006, 16 (02) : 29R - 37R