標題: | Synthesis of a fluorogenic substrate for alpha-L-iduronidase |
作者: | Lu, Fu-Chieh Lico, Larry S. Hung, Shang-Cheng 應用化學系 Department of Applied Chemistry |
關鍵字: | L-Iduronic acid;Mitsunobu-type glycosylation;mucopolysaccharidosis;fluorogenic substrate;alpha-L-iduronidase |
公開日期: | 2013 |
摘要: | An alternative reaction pathway towards the preparation of an L-idopyranose derivative and its application to the synthesis of the alpha-L-iduronidase fluorogenic substrate 4-methylcoumarin-7-yl-alpha-L-iduronic acid as well as its 3-undecyl derivative are described. The L-ido sugar was prepared by converting the commercially available diacetone-alpha-D-glucose to methyl 1,2,3,4-tetra-O-acetyl-L-idopyranuronate via oxidation, esterification, and regioselective acetylation of the key intermediate 1,2:3,5-di-O-isopropylidene-beta-L-idofuranose. Mitsunobu-type glycosylation was employed in the coupling of the L-ido donor with the 4-methylcoumarin acceptors. This newly developed route reduced the difficulties previously encountered in the synthesis of the alpha-L-iduronidase fluorogenic substrate. |
URI: | http://hdl.handle.net/11536/22905 |
ISSN: | 1551-7004 |
期刊: | ARKIVOC |
起始頁: | 13 |
結束頁: | 21 |
顯示於類別: | 期刊論文 |