Total Synthesis of a Glycoglycerolipid from Meiothermus taiwanensis through a One-Pot Glycosylation Reaction and Exploration of its Immunological Properties

被引：9

作者：

Ghosh, Bhaswati ^{[1
]}

Lai, Yen-Hsun ^{[1
]}

Shih, Yu-Yin ^{[2
]}

Pradhan, Tapan Kumar ^{[1
]}

Lin, Chun-Hung ^{[2
]}

Mong, Kwok-Kong Tony ^{[1
]}

机构：

[1] NCTU, Dept Appl Chem, Hsinchu, Taiwan

[2] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2013年 / 8卷 / 12期

关键词：

glycosylation; immunology; lipids; natural products; total synthesis; STRUCTURAL ELUCIDATION; LIPOTEICHOIC ACID; TNF-ALPHA; PHOSPHOGLYCOLIPIDS; STRATEGY; THIOGLYCOSIDES; IL-1-BETA; LIBRARY; THERMUS; UNITS;

D O I：

10.1002/asia.201300933

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of a glycoglycerolipid isolate of Meiothermus taiwanensis and its truncated structural analogues is reported. Our synthesis employed DMF-modulated and low-concentration glycosylation reactions for the construction of - and -glycosidic bonds in the absence of participating protecting groups. Further simplification of the synthesis was achieved by employing a low-concentration one-pot glycosylation procedure. Preliminary immunological studies showed that one of the truncated structural analogues suppressed the cytokine production of THP-1 monocytes.

引用

页码：3191 / 3199

页数：9

共 37 条

[1] TNF-α, IL-6, and IL-1 expression is inhibited by GAS6 in monocytes/macrophages
Alciato, Federica
Sainaghi, Pier Paolo
Sola, Daniele
Castello, Luigi
Avanzi, Gian Carlo
[J]. JOURNAL OF LEUKOCYTE BIOLOGY, 2010, 87 (05) : 869 - 875
[2] The stimulating adventure of KRN 7000
Banchet-Cadeddu, Aline
Henon, Eric
Dauchez, Manuel
Renault, Jean-Hugues
Monneaux, Fanny
Haudrechy, Arnaud
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (09) : 3080 - 3104
[3] Chemical synthesis of a glycolipid library by a solid-phase strategy allows elucidation of the structural specificity of immunostimulation by rhamnolipids
Bauer, Joerg
Brandenburg, Klaus
Zaehringer, Ulrich
Rademann, Joerg
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (27) : 7116 - 7124
[4] STUDY OF C-13H COUPLING-CONSTANTS IN HEXOPYRANOSES
BOCK, K
PEDERSEN, C
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03): : 293 - 299
[5] Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars
Bongat, Aileen F. G.
Demchenko, Alexei V.
[J]. CARBOHYDRATE RESEARCH, 2007, 342 (3-4) : 374 - 406
[6] Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria
Cao, Benjamin
Chen, Xingqiang
Yamaryo-Botte, Yoshiki
Richardson, Mark B.
Martin, Kirstee L.
Khairallah, George N.
Rupasinghe, Thusita W. T.
O'Flaherty, Roisin M.
O'Hair, Richard A. J.
Ralton, Julie E.
Crellin, Paul K.
Coppel, Ross L.
McConville, Malcolm J.
Williams, Spencer J.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) : 2175 - 2190
[7] Carlson NG, 1999, J IMMUNOL, V163, P3963
[8] Solvent Participation in a One-Pot Glycosylation Strategy (SPOG)
Chao, Chin-Sheng
Yen, Yu-Fang
Hung, Wei-Cheng
Mong, Kwok-Kong Tony
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (06) : 879 - 884
[9] Low-Concentration 1,2-trans β-Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis
Chao, Chin-Sheng
Li, Chen-Wei
Chen, Min-Chun
Chang, Shih-Sheng
Mong, Kwok-Kong Tony
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (41) : 10972 - 10982
[10] Chen MY, 2002, INT J SYST EVOL MICR, V52, P1647, DOI [10.1099/ijs.0.02189-0, 10.1099/00207713-52-5-1647]

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