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