Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-
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- 作者：Thomas B. Mercer ; Sarah F. Jenkinson ; Barbara Bartholomew ; Robert J. Nash ; Saori Miyauchi ; Atsushi Kato ; George W.J. Fleet
- 刊名：Tetrahedron: Asymmetry
- 出版年：2009
- 出版时间：20 October 2009
- 年：2009
- 卷：20
- 期：20
- 页码：2368-2373
- 全文大小：680 K
文摘
Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-l-lyxitol (LIL). DIL showed potent [Ki = 0.13 μM]—and LIL showed weak [Ki = 113 μM]—competitive inhibition of α-d-galactosidase. Both enantiomers N-benzyl-DIL [Ki = 64 μM] and N-benzyl-LIL [Ki = 13 μM] were moderate competitive inhibitors of naringinase, an α-l-rhamnosidase.