Asymmetric synthesis of potent glycosidase and very potent α-mannosidase inhibitors: 4-amino-4-deoxy-l-erythrose and 4-amino-4,5-dideoxy-l-ribose

作者: Jean-Bernard Behr , Carine Chevrier , Albert Defoin , Céline Tarnus , Jacques Streith

DOI: 10.1016/S0040-4020(02)01512-0

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摘要: Abstract Pyrrolidine amino-sugars, cyclic iminoalditols as well linear aminoalditols in 4-amino- l -erythrose and 4-amino-5-deoxy- -ribose series were synthesised by asymmetric hetero-Diels–Alder reaction followed chemical transformations. 4-Amino-4-deoxy- 4-amino-4,5-dideoxy- potent β- d -glucosidase, α- -mannosidase, -galactosidase inhibitors. We have shown that the ribose derivative was a very inhibitor of -mannosidase.

参考文章(43)
Yu-Teh Li, Studies on the Glycosidases in Jack Bean Meal I. ISOLATION AND PROPERTIES OF α-MANNOSIDASE Journal of Biological Chemistry. ,vol. 242, pp. 5474- 5480 ,(1967) , 10.1016/S0021-9258(18)99383-X
Seiichiro Ogawa, Takayuki Morikawa, Synthesis and biological evaluation of α-mannosidase inhibitory activity of three deoxy derivatives of mannostatin A Bioorganic & Medicinal Chemistry Letters. ,vol. 9, pp. 1499- 1504 ,(1999) , 10.1016/S0960-894X(99)00224-3
Bryan Winchester, George W.J. Fleet, Amino-sugar glycosidase inhibitors: versatile tools for glycobiologists Glycobiology. ,vol. 2, pp. 199- 210 ,(1992) , 10.1093/GLYCOB/2.3.199
Louis Provencher, Darryl H. Steensma, Chi-Huey Wong, Five-membered ring azasugars as potent inhibitors of α-L-rhamnosidase (naringinase) from Penicillium decumbens Bioorganic & Medicinal Chemistry. ,vol. 2, pp. 1179- 1188 ,(1994) , 10.1016/S0968-0896(00)82069-6
Eisaku Tsujii, Makoto Muroi, Nobue Shiragami, Akira Takatsuki, Nectrisine is a potent inhibitor of α-glucosidases, demonstrating activities similarly at enzyme and cellular levels Biochemical and Biophysical Research Communications. ,vol. 220, pp. 459- 466 ,(1996) , 10.1006/BBRC.1996.0427
Peter Bach, Mikael Bols, Synthesis of an 1-azaglucose analogue with ring-oxygen retained Tetrahedron Letters. ,vol. 40, pp. 3461- 3464 ,(1999) , 10.1016/S0040-4039(99)00423-2
Gary E. Keck, Travis T. Wager, Stanton F. McHardy, Reductive cleavage of NO bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide Tetrahedron. ,vol. 55, pp. 11755- 11772 ,(1999) , 10.1016/S0040-4020(99)00486-X
Jean-Bernard Behr, Albert Defoin, Naheed Mahmood, Jacques Streith, (±)-4-Amino-4,5-dideoxyribose, (±)-4-amino-4-deoxyerythrose, and (±)-dihydroxyproline derivatives from N-dienyl-γ-lactams Helvetica Chimica Acta. ,vol. 78, pp. 1166- 1177 ,(1995) , 10.1002/HLCA.19950780510
V. VanRheenen, R.C. Kelly, D.Y. Cha, An improved catalytic OsO4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant Tetrahedron Letters. ,vol. 17, pp. 1973- 1976 ,(1976) , 10.1016/S0040-4039(00)78093-2