Determination and measurement of unusual metabolites of bile acid multi-conjugates excreted in a patient with Nimann-Pick disease type C1.
Determination and measurement of unusual metabolites of bile acid multi-conjugates excreted in a patient with Nimann-Pick disease type C1.
批准号:
15510182
负责人:
IIDA Takashi
金额:
$2.24万
依托单位:
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (C)
财政年份:
2003
资助国家:
日本
项目状态:
已结题
起止时间:
2003 至 2004
中文摘要
本文描述了3β,7β-二羟基-5-胆碱-24-酸的化学合成,硫酸在C-3, n-乙酰氨基葡萄糖(GlcNAc)在C-7和甘氨酸(或牛磺酸)在C-24,这是罕见的,主要代谢物排泄的尼曼-匹克病C1型患者的尿液。还制备了3β-羟基-7-氧-5-胆碱-24-酸的类似双共轭物。涉及的主要反应有:1)在煮沸的甲苯中,在CdCO_3存在下,3 - β-叔丁基二甲基硅氧烷(TBDMSi)-7 - β-羟基-5-胆碱-24-oate在C-7处与2-乙酰氨基-1α-氯-1,2-二脱氧-3,4,6-三-o -乙酰-d -葡萄糖吡喃糖在C-3处与三氧化硫-三甲胺配合物在吡啶中磺化生成3 - β-TBDMSi-7 - β- glcnac。3)在DMF中使用4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基酰氯作为偶联剂,在3β-磺基-7β- glcnac偶联物的C-24位点与甘氨酸甲酯盐酸盐(或牛磺酸)直接氨基酰化。采用液相色谱-质谱联用电喷雾探针对多共轭胆汁酸在正、负电离模式下的结构进行了表征。
英文摘要
The chemical synthesis of 3β,7β-dihydroxy-5-cholen-24-oic acid triply conjugated by sulfuric acid at C-3,N-acetylglucosamine (GlcNAc) at C-7 and glycine (or taurine) at C-24, which are unusual, major metabolites excreted in urine of a patient with Niemann-Pick diseases type C1,is described. Analogous double-conjugates of 3β-hydroxy-7-oxo-5-cholen-24-oic acid were also prepared. The principal reactions involved were : 1)β-D-N-acetylglueosaminidation at C-7 of methyl 3β-tert-butyldimethylsilyloxy (TBDMSi)-7β-hydroxy-5-cholen-24-oate with 2-acetamido-1α-chloro-1,2-dideoxy-3,4,6-tri-O-acetyl-D-glucopyranose in the presence of CdCO_3 in boiling toluene, 2)sulfation at C-3 of the resulting 3β-TBDMSi-7β-GlcNAc with sulfur trioxide-trimethylamine complex in pyridine, and 3)direct aminoacyl amidation at C-24 of the 3β-sulfo-7β-GlcNAc conjugate with glycine methyl ester hydrochloride (or taurine) using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as a coupling agent in DMF. The structures of the multi-conjugated bile acids were characterized by liquid chromatography-mass spectrometry with electrospray ionization probe under the positive and the negative ionization modes.
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飯田 隆: "A Comparative Study of Remote Oxy-functionalization of Unativated Carbons in 5β-Steroids by Dimethyldioxirane and 2,6-Dichloropyridine N-Oxide/Ruthenium Porphyrin/HBr."Arkivoc.. viii. 171-179 (2003)
Takashi Iida:“二甲基二环氧乙烷和 2,6-二氯吡啶 N-氧化物/钌卟啉/HBr 对 5β-类固醇中未活化碳的远程氧官能化的比较研究”Arkivoc.. viii。
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An Improved Method for the Capillary Gas Chromatographic Derivatization of Polyhydroxylated Steroids Having tert.-Hydroxyl Groups.
具有叔羟基的多羟基类固醇的毛细管气相色谱衍生化的改进方法。
DOI:
--
发表时间:
2003
期刊:
Anal.Sci. 19(9)
影响因子:
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作者:
[T.Iida, et al.]
通讯作者:
et al.
飯田 隆: "Functionalization of Unactivated Carbons in 3α,6- and 3α, 24-Dihydroxy-5β-cholane Derivatives by Dimethyldioxirane."Lipids. 38/3. 281-287 (2003)
Takashi Iida:“二甲基二环氧乙烷对 3α,6- 和 3α, 24-二羟基-5β-胆烷衍生物的功能化”38/3 (2003)。
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飯田 隆: "An Improved Method for the Capillary Gas Chromatographic Derivatization of Polyhydroxylated Steroids Having tert.-Hydroxyl Groups."Anal.Sci.. 19/9. 1317-1321 (2003)
Takashi Iida:“具有叔羟基的多羟基类固醇的毛细管气相色谱衍生化的改进方法。”Anal.Sci. 19/9 (2003)。
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飯田 隆(編著): "イラストで見る化学実験の基礎知識"丸善(株). 255 (2003)
饭田隆(编):《通过插图了解化学实验的基础知识》Maruzen Co., Ltd. 255(2003)
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