Systematic chemoenzymatic synthesis of O-sulfated sialyl Lewis x antigens

被引:0
作者
Santra, Abhishek [1 ]
Yu, Hai [1 ]
Tasnima, Nova [1 ]
Muthana, Musleh M. [1 ]
Li, Yanhong [1 ]
Zeng, Jie [1 ,2 ]
Kenyon, Nicholas J. [3 ]
Louie, Angelique Y. [4 ]
Chen, Xi [1 ]
机构
[1] Univ Calif Davis, Dept Chem, One Shields Ave, Davis, CA 95616 USA
[2] Henan Inst Sci & Technol, Sch Food Sci, Xinxiang 453003, Peoples R China
[3] Univ Calif Davis, Dept Internal Med, Div Pulm Crit Care & Sleep Med, Davis, CA 95616 USA
[4] Univ Calif Davis, Dept Biomed Engn, Davis, CA 95616 USA
关键词
ENDOTHELIAL-DERIVED LIGAND; LE(X) GANGLIOSIDE ANALOGS; REAL CARBOHYDRATE LIGAND; MAJOR CAPPING GROUP; L-SELECTIN; SIGLEC-F; AUTOMATED SYNTHESIS; HEPARAN-SULFATE; BUILDING-BLOCK; GLYCANS;
D O I
10.1039/c5sc04104j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
O-Sulfated sialyl Lewis x antigens play important roles in nature. However, due to their structural complexity, they are not readily accessible by either chemical or enzymatic synthetic processes. Taking advantage of a bacterial sialyltransferase mutant that can catalyze the transfer of different sialic acid forms from the corresponding sugar nucleotide donors to Lewis x antigens, which are fucosylated glycans, as well as an efficient one-pot multienzyme (OPME) sialylation system, O-sulfated sialyl Lewis x antigens containing different sialic acid forms and O-sulfation at different locations were systematically synthesized by chemoenzymatic methods.
引用
收藏
页码:2827 / 2831
页数:5
相关论文
共 56 条
[11]   Advances in the Biology and Chemistry of Sialic Acids [J].
Chen, Xi ;
Varki, Ajit .
ACS CHEMICAL BIOLOGY, 2010, 5 (02) :163-176
[12]   A GENERAL, CATALYTIC, AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
COREY, EJ ;
LINK, JO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1906-1908
[13]   Automated synthesis of sialylated oligosaccharides [J].
Esposito, Davide ;
Hurevich, Mattan ;
Castagner, Bastien ;
Wang, Cheng-Chung ;
Seeberger, Peter H. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1601-1609
[14]   High and low affinity carbohydrate ligands revealed for murine SIGN-R1 by carbohydrate array and cell binding approaches, and differing specificities for SIGN-R3 and langerin [J].
Galustian, C ;
Park, CG ;
Chai, WG ;
Kiso, M ;
Bruening, SA ;
Kang, YS ;
Steinman, RM ;
Feizi, T .
INTERNATIONAL IMMUNOLOGY, 2004, 16 (06) :853-866
[15]   Convergent synthesis of a hexasaccharide corresponding to the cell wall O-antigen of Escherichia coli O41 [J].
Ghosh, Tamashree ;
Santra, Abhishek ;
Misra, Anup Kumar .
RSC ADVANCES, 2014, 4 (01) :54-60
[16]   6'-SULFATED SIALYL-LEWIS-X IS A MAJOR CAPPING GROUP OF GLYCAM-1 [J].
HEMMERICH, S ;
ROSEN, SD .
BIOCHEMISTRY, 1994, 33 (16) :4830-4835
[17]   IDENTIFICATION OF THE SULFATED MONOSACCHARIDES OF GLYCAM-1, AN ENDOTHELIAL-DERIVED LIGAND FOR L-SELECTIN [J].
HEMMERICH, S ;
BERTOZZI, CR ;
LEFFLER, H ;
ROSEN, SD .
BIOCHEMISTRY, 1994, 33 (16) :4820-4829
[18]   STRUCTURE OF THE O-GLYCANS IN GLYCAM-1, AN ENDOTHELIAL-DERIVED LIGAND FOR L-SELECTIN [J].
HEMMERICH, S ;
LEFFLER, H ;
ROSEN, SD .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (20) :12035-12047
[19]   Eosinophil-Selective Binding and Proapoptotic Effect in Vitro of a Synthetic Siglec-8 Ligand, Polymeric 6′-Sulfated Sialyl Lewis X [J].
Hudson, Sherry A. ;
Bovin, Nicolai V. ;
Schnaar, Ronald L. ;
Crocker, Paul R. ;
Bochner, Bruce S. .
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2009, 330 (02) :608-612
[20]   TOTAL SYNTHESIS OF 3'-O-SIALYL, 6'-O-SULFO LEWIS(X), NEUAC-ALPHA-2-]3(6-O-SO3NA)GA1-BETA-1-]4(FUC-ALPHA-1-]3)-GLCNAC-BETA-OME - A MAJOR CAPPING GROUP OF GLYCAM-I [J].
JAIN, RK ;
VIG, R ;
RAMPAL, R ;
CHANDRASEKARAN, EV ;
MATTA, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12123-12124