己醛醣酸鹽水解酵素受質與抑制劑的合成

奚偉恩

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己醛醣酸鹽水解酵素受質與抑制劑的合成

Synthesis of the α-L-iduronidase substrate and inhibitors

奚偉恩 , Masters　　Advisor：羅禮強　　Co-advisor ：鄭偉杰

英文

亞胺醣；環硝；艾杜糖；己醛醣酸鹽水解酵素；抑制劑； α-L-iduronidase ； inhibitor ； cyclic nitrone ； 4MU-α-IdoA

Abstract │ Reference (27) │ Altmetrics

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α-L-iduronidase (IDUA), an endoglycosidase, cleaves the 1,4-glycosidic bond between L-iduronic acids (L-IdoA) and D-glucosamine (or D-galactosamine) in heparin and heparan sulfate. The inhibition study of IDUA is important but rarely mentioned in the literature because materials such as L-Idopyranose and L-IdoA are not commercially available. And substrates are expensive. Thus, an economical source of IDUA substrate is needed.
    Currently, IDUA has been found to involve with a genetically inherited lysosomal storage disease, mucopolysaccharidosis I (MPS1).
    A synthetic route started from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, through C-5 inversion of configuration gave a key intermediate 3-OBn-L-idopyranose, followed by trichloroacetimidate-mediated glycosylation with 4-methylumbelliferone and selective primary alcohol oxidation by TEMPO catalyst to give the 4-methylumbelliferyl α-L-iduronide (4MU-α-IdoA) as a fluorogenic substrate for IDUA.
    To mimic the oxocarbenium ion generated during IDUA hydrolysis, 2-(aminomethyl) pyrrolidine iminosugar scaffolds were prepared using a five-membered chiral cyclic nitrone as a key intermediate, followed by N-protection and selective oxidation by TEMPO/NaOCl/ NaClO2 to give the aza-L-iduronic acid analogs. An acid was coupled with a scaffold to. diversify at primary amine as a model for further inhibition study.

Reference ( 27 ) 〈TOP〉

1. Nieman, C. E.; Wong, A. W.; He, S.; Hopwood, J. J.; Withers, S. G., Family 39 α-l-Iduronidases and β-d-Xylosidases React through Similar Glycosyl−Enzyme Intermediates: Identification of the Human Iduronidase Nucleophile†. Biochemistry 2003, 42 (26), 8054-8065.
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2. Sudhakar Sarath, C., Mucopolysaccharidosis type I: Homology modeling and docking analysis of the lysosomal enzyme, human α-L-iduronidase. African Journal of Pharmacy and Pharmacology 2012, 6 (27).
連結：
3. Cohen, F. E.; Kelly, J. W., Therapeutic approaches to protein-misfolding diseases. Nature 2003, 426 (6968), 905-909.
連結：
4. Pastores, G. M.; Arn, P.; Beck, M.; Clarke, J. T.; Guffon, N.; Kaplan, P.; Muenzer, J.; Norato, D. Y.; Shapiro, E.; Thomas, J., The MPS I registry: design, methodology, and early findings of a global disease registry for monitoring patients with Mucopolysaccharidosis Type I. Molecular genetics and metabolism 2007, 91 (1), 37-47.
連結：
5. Terlato, N. J.; Cox, G. F., Can mucopolysaccharidosis type I disease severity be predicted based on a patient's genotype? A comprehensive review of the literature. Genetics in medicine : official journal of the American College of Medical Genetics 2003, 5 (4), 286-94.
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