Synthesis of 1,2-cis-Homoiminosugars Derived from GIcNAc and GaINAc Exploiting a β-Amino Alcohol Skeletal Rearrangement

被引：30

作者：

Bleriot, Yves ^{[1
]}

Auberger, Nicolas ^{[1
]}

Jagadeesh, Yerri ^{[1
]}

Gauthier, Charles ^{[1
]}

Prencipe, Giuseppe ^{[2
]}

Anh Tuan Tran ^{[2
]}

Marrot, Jerome ^{[3
]}

Desire, Jerome ^{[1
]}

Yamamoto, Arisa ^{[4
]}

Kato, Atsushi ^{[4
]}

Sollogoub, Matthieu ^{[2
]}

机构：

[1] Univ Poitiers, Glycochem Grp, Organ Synth Team, UMR 7285,IC2MP,CNRS, F-86073 Poitiers 9, France

[2] Univ Paris 06, Sorbonne Univ, Inst Univ France, UMR 8232,IPCM,LabEx MiChem,CNRS, F-75005 Paris, France

[3] Univ Versailles, UMR 8180, CNRS, Inst Lavoisier Versailles, F-78035 Versailles, France

[4] Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 21期

关键词：

IMINOSUGAR C-GLYCOSIDES; MIMICKING MONOSACCHARIDES; ALPHA-HOMONOJIRIMYCIN; D-GLUCOSE; POTENT; INHIBITORS; 2-ACETAMIDO-1,2-DIDEOXYNOJIRIMYCIN; ACCESS; 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL; ISOMERIZATION;

D O I：

10.1021/ol502926f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these a-d-GlcNAc and a-d-GalNAc mimics utilizes a beta-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring a-HGJ and a-HNJ. The a-d-GlcNAc-configured iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide. Preliminary glycosidase inhibition evaluation indicates that the a-d-GalNAc-configured homoiminosugar is a potent and selective a-N-acetylgalactosaminidase inhibitor.

引用

页码：5512 / 5515

页数：4

共 38 条

[11] Access to piperidine imino-C-glycosides via stereoselective thiazole-based aminohomologation of pyranoses [J].

Dondoni, Alessandro ;

Nuzzi, Andrea .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7574-7582

[12] SYNTHESIS OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL AND OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL, A POTENT AND SPECIFIC INHIBITOR OF A NUMBER OF BETA-N-ACETYLGLUCOSAMINIDASES [J].

FLEET, GWJ ;

SMITH, PW ;

NASH, RJ ;

FELLOWS, LE ;

PAREKH, RB ;

RADEMACHER, TW .

CHEMISTRY LETTERS, 1986, (07) :1051-1054

[13] SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S, 3R, 4R, 5R-TRIHYDROXYPIPECOLIC ACID AND 2S, 3R, 4R, 5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-ALPHA-D-MANNOFURANOSIDE [J].

FLEET, GWJ ;

FELLOWS, LE ;

SMITH, PW .

TETRAHEDRON, 1987, 43 (05) :979-990

[14] 2-ACETAMIDO-1,2-DIDEOXYNOJIRIMYCIN - AN IMPROVED SYNTHESIS [J].

FURNEAUX, RH ;

GAINSFORD, GJ ;

LYNCH, GP ;

YORKE, SC .

TETRAHEDRON, 1993, 49 (42) :9605-9612

[15] An approach to 8 stereoisomers of homonojirimycin from D-glucose via kinetic & thermodynamic azido-γ-lactones [J].

Glawar, Andreas F. G. ;

Jenkinson, Sarah F. ;

Newberry, Scott J. ;

Thompson, Amber L. ;

Nakagawa, Shinpei ;

Yoshihara, Akihide ;

Akimitsu, Kazuya ;

Izumori, Ken ;

Butters, Terry D. ;

Kato, Atsushi ;

Fleet, George W. J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (40) :6886-6899

[16] A novel approach to the 1-deoxynojirimycin system: Synthesis from sucrose of 2-acetamido-1,2-dideoxynojirimycin, as well as some 2-N-modified derivatives [J].

Gradnig, G ;

Legler, G ;

Stutz, AE .

CARBOHYDRATE RESEARCH, 1996, 287 :49-57

[17] Synthesis of 6,6′-ether linked disaccharides from D-allose, D-galactose, D-glucose and D-mannose;: evidence on the structure of coyolosa [J].

Haines, AH .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (16) :2352-2358

[18] An in-depth study on ring-closing metathesis of carbohydrate-derived α-alkoxyacrylates:: Efficient syntheses of DAH, KDO, and 2-deoxy-β-KDO [J].

Hekking, Koen F. W. ;

Moelands, Marcel A. H. ;

van Delft, Floris L. ;

Rutjes, Floris P. J. T. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6444-6450

[19] Iminosugar C-Glycoside Analogues of α-D-GlcNAc-1-Phosphate: Synthesis and Bacterial Transglycosylase Inhibition [J].

Hsu, Che-Hsiung ;

Schelwies, Mathias ;

Enck, Sebastian ;

Huang, Lin-Ya ;

Huang, Shih-Hsien ;

Chang, Yi-Fan ;

Cheng, Ting-Jen Rachel ;

Cheng, Wei-Chieh ;

Wong, Chi-Huey .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (18) :8629-8637

[20] GLYCOSYLATION INHIBITORS IN BIOLOGY AND MEDICINE [J].

JACOB, GS .

CURRENT OPINION IN STRUCTURAL BIOLOGY, 1995, 5 (05) :605-611

← 1 2 3 4 →