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2005
Carbohydrates
U 0500
α-1-C-Alkyl-1-deoxynojirimycin Derivatives as Potent and Selective Inhibitors of
Isomaltase: Remarkable Effect of the Alkyl Chain Length on Glyco15- 183 Intestinal
sidase Inhibitory Profile. — Cross-metathesis reaction, cf. (I)—(III), as the key step
provides the nonyldeoxynojirimycin (V). The key step yields the iminoglycolipid (III)
with excellent stereoselectivity as the only isomer. A marked dependence of the selectivity and potency of the inhibitors on the position of the alkyl chain (α-1, β-1 or
N-alkyl) is observed. α-1-Nonyl derivative (V) is a potent and selective inhibitor of intestinal isomaltase. — (GODIN, G.; COMPAIN*, P.; MARTIN, O. R.; IKEDA, K.; YU,
L.; ASANO, N.; Bioorg. Med. Chem. Lett. 14 (2004) 24, 5991-5995; Inst. Chim. Org.
Anal., CNRS, Fac. Sci., Univ. Orleans, F-45067 Orleans, Fr.; Eng.) —
H. Hoennerscheid
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