Total Syntheses of Casuarine and Its 6-O-α-Glucoside: Complementary Inhibition towards Glycoside Hydrolases of the GH31 and GH37 Families

被引：88

作者：

Cardona, Francesca ^{[1
]}

Parmeggiani, Camilla ^{[1
]}

Faggi, Enrico ^{[1
]}

Bonaccini, Claudia ^{[2
]}

Gratteri, Paola ^{[2
]}

Sim, Lyann ^{[3
,4
]}

Gloster, Tracey M. ^{[5
]}

Roberts, Shirley ^{[5
]}

Davies, Gideon J. ^{[5
]}

Rose, David R. ^{[3
,4
]}

Goti, Andrea ^{[1
]}

机构：

[1] Univ Florence, Dept Organ Chem U Schiff, Lab Design Synth & Study Biol Active Heterocycles, I-50019 Sesto Fiorentino, FI, Italy

[2] Univ Florence, Lab Mol Modeling Cheminformat & QSAR, Lab Design Synth & Study Biol Active Heterocycles, Dept Pharmaceut Sci, I-50019 Sesto Fiorentino, FI, Italy

[3] Univ Toronto, Ontario Canc Inst, Toronto, ON M5G 1L7, Canada

[4] Univ Toronto, Dept Med Biophys, Toronto, ON M5G 1L7, Canada

[5] Univ York, York Struct Biol Lab, Dept Chem, York YO10 5YW, N Yorkshire, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 07期

基金：

美国国家卫生研究院; 英国生物技术与生命科学研究理事会; 美国国家科学基金会; 加拿大自然科学与工程研究理事会;

关键词：

enzyme structures; maltase glucoamylase; natural products; total synthesis; trehalase; INTESTINAL MALTASE-GLUCOAMYLASE; POLYHYDROXYLATED PYRROLIZIDINES; STEREOSELECTIVE-SYNTHESIS; PHENYLDIMETHYLSILYL GROUP; SILAFUNCTIONAL COMPOUNDS; ENZYMATIC-SYNTHESIS; ORGANIC-SYNTHESIS; CYCLOADDITION; (+)-CASUARINE; TREHALASE;

D O I：

10.1002/chem.200801578

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total synthesis of naturally occurring casuarine (1) and the first total synthesis of casuarine 6-O-alpha-glucoside (2) were achieved through complete stereoselective nitrone cycloaddition, Tamao-Fleming oxidation and selective alpha-glucosylation as key steps. Biological assays of the two compounds proved their strong and selective inhibitory properties towards glucoamylase NtMGAM and trehalase Tre37A, respectively, which place them among the most powerful inhibitors of these enzymes. The structural determination of the complexes of NtMGAM with 1 and of Tre37A with 2 revealed interesting similarities in the catalytic sites of these two enzymes which belong to different families and clans.

引用

页码：1627 / 1636

页数：10

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