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

来源：

CHEMICAL SCIENCE | 2016年 / 7卷 / 04期

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

页码：2827 / 2831

页数：5

共 56 条

[11] Advances in the Biology and Chemistry of Sialic Acids
Chen, Xi
Varki, Ajit
[J]. ACS CHEMICAL BIOLOGY, 2010, 5 (02) : 163 - 176
[12] A GENERAL, CATALYTIC, AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
COREY, EJ
LINK, JO
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1906 - 1908
[13] Automated synthesis of sialylated oligosaccharides
Esposito, Davide
Hurevich, Mattan
Castagner, Bastien
Wang, Cheng-Chung
Seeberger, Peter H.
[J]. 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
Galustian, C
Park, CG
Chai, WG
Kiso, M
Bruening, SA
Kang, YS
Steinman, RM
Feizi, T
[J]. INTERNATIONAL IMMUNOLOGY, 2004, 16 (06) : 853 - 866
[15] Convergent synthesis of a hexasaccharide corresponding to the cell wall O-antigen of Escherichia coli O41
Ghosh, Tamashree
Santra, Abhishek
Misra, Anup Kumar
[J]. RSC ADVANCES, 2014, 4 (01) : 54 - 60
[16] 6'-SULFATED SIALYL-LEWIS-X IS A MAJOR CAPPING GROUP OF GLYCAM-1
HEMMERICH, S
ROSEN, SD
[J]. BIOCHEMISTRY, 1994, 33 (16) : 4830 - 4835
[17] IDENTIFICATION OF THE SULFATED MONOSACCHARIDES OF GLYCAM-1, AN ENDOTHELIAL-DERIVED LIGAND FOR L-SELECTIN
HEMMERICH, S
BERTOZZI, CR
LEFFLER, H
ROSEN, SD
[J]. BIOCHEMISTRY, 1994, 33 (16) : 4820 - 4829
[18] STRUCTURE OF THE O-GLYCANS IN GLYCAM-1, AN ENDOTHELIAL-DERIVED LIGAND FOR L-SELECTIN
HEMMERICH, S
LEFFLER, H
ROSEN, SD
[J]. 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
Hudson, Sherry A.
Bovin, Nicolai V.
Schnaar, Ronald L.
Crocker, Paul R.
Bochner, Bruce S.
[J]. 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
JAIN, RK
VIG, R
RAMPAL, R
CHANDRASEKARAN, EV
MATTA, KL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 12123 - 12124

← 1 2 3 4 5 6 →