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Molecules 2012, 17(3), 3058-3081; doi:10.3390/molecules17033058
Article

Synthesis of Amino Core Compounds of Galactosyl Phytosyl Ceramide Analogs for Developing iNKT-Cell Inducers

1, 2, 2, 2, 2, 3, 2,4, 2, 2 and 2,5,*
1 Department of Neurosurgery, Chang Gung Memorial Hospital and Department of Medicine, Chang Gung University, Taoyuan 33305, Taiwan 2 Department of Biomedical Engineering and Environmental Sciences, National Tsing-Hua University, No. 101 sec.2, Guang-Fu Rd., Hsinchu 30043, Taiwan 3 Department of Medical Research, Taichung Veterans General Hospital, Taichung 40705, Taiwan 4 Department of Obstetrics and Gynecology, Chang Bing Show Chwan Memorial Hospital, Lukang Zhen, Changhua 50544, Taiwan 5 Institute of Nuclear Engineering and Science, National Tsing-Hua University, Hsinchu 30043, Taiwan
* Author to whom correspondence should be addressed.
Received: 20 January 2012 / Revised: 1 March 2012 / Accepted: 6 March 2012 / Published: 12 March 2012
(This article belongs to the Special Issue Parallel Synthesis)
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Abstract

1-Aminophytosphingosine and 6-aminogalactosyl phytosphingosine were prepared in 61% and 40% yield libraries with 44 carboxylic acids showed that a 4-butylbenzoic acid-derived product exe, respectively. Glycosylation using benzoyl-protected lipid resulted in better a-selectivity for ceramide analogs, but the yield was less than that obtained with benzyl moieties. Screening the amide rted less cytotoxicity. These analogs were purified for validation of immunological potencies and the a-GalCer analog but not the sphingosine analog stimulated human iNKT cell population.
Keywords: phytosphingosine; library; cancer; immune; glycosylation phytosphingosine; library; cancer; immune; glycosylation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Huang, Y.-C.; Chiang, L.-W.; Chang, K.-S.; Su, W.-C.; Lin, Y.-H.; Jeng, K.-C.; Lin, K.-I.; Liao, K.-Y.; Huang, H.-L.; Yu, C.-S. Synthesis of Amino Core Compounds of Galactosyl Phytosyl Ceramide Analogs for Developing iNKT-Cell Inducers. Molecules 2012, 17, 3058-3081.

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