Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol [a potent competitive inhibitor of alpha-D-galactosidase] and of 1,4-dideoxy-1,4-imino-L-lyxitol [a weak competitive inhibitor of alpha-D-galactosidase] inhibit naringinase, an alpha-L-rhamnosidase competitively

Mercer, TB; Jenkinson, SF; Bartholomew, B; Nash, RJ; Miyauchi, S; Kato, A; Fleet, GWJ

Abstract:

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. © 2009 Elsevier Ltd. All rights reserved.

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APA Style

Mercer, T. B., Jenkinson, S. F., Bartholomew, B., Nash, R. J., Miyauchi, S., Kato, A., & Fleet, G. W. J. (2009). Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol [a potent competitive inhibitor of alpha-D-galactosidase] and of 1,4-dideoxy-1,4-imino-L-lyxitol [a weak competitive inhibitor of alpha-D-galactosidase] inhibit naringinase, an alpha-L-rhamnosidase competitively. TETRAHEDRON-ASYMMETRY, 20(20), 2368–2373.

MLA Style

Mercer, T. B., et al. “Looking Glass Inhibitors: Both Enantiomeric N-Benzyl Derivatives of 1,4-Dideoxy-1,4-Imino-D-Lyxitol [a Potent Competitive Inhibitor of Alpha-D-Galactosidase] and of 1,4-Dideoxy-1,4-Imino-L-Lyxitol [a Weak Competitive Inhibitor of Alpha-D-Galactosidase] Inhibit Naringinase, an Alpha-L-Rhamnosidase Competitively.” TETRAHEDRON-ASYMMETRY, vol. 20, no. 20, 2009, pp. 2368–73.

Chicago Style

Mercer, TB, SF Jenkinson, B Bartholomew, RJ Nash, S Miyauchi, A Kato, and GWJ Fleet. 2009. “Looking Glass Inhibitors: Both Enantiomeric N-Benzyl Derivatives of 1,4-Dideoxy-1,4-Imino-D-Lyxitol [a Potent Competitive Inhibitor of Alpha-D-Galactosidase] and of 1,4-Dideoxy-1,4-Imino-L-Lyxitol [a Weak Competitive Inhibitor of Alpha-D-Galactosidase] Inhibit Naringinase, an Alpha-L-Rhamnosidase Competitively.” TETRAHEDRON-ASYMMETRY 20 (20): 2368–73.
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