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

Thomas B. Mercer; Sarah F. Jenkinson; Barbara Bartholomew; Robert J. Nash; Saori Miyauchi; Atsushi Kato; George W. J. Fleet

doi:10.1016/j.tetasy.2009.10.004

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

Thomas B. Mercer, Sarah F. Jenkinson, Barbara Bartholomew, Robert J. Nash, Saori Miyauchi, Atsushi Kato, George W. J. Fleet

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

44 Citations (Scopus)

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 [K(i) = 0.13 mu M]-and LIL showed weak [K(i) = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K(i) = 64 mu M] and N-benzyl-LIL [K(i) = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase.

Original language	English
Pages (from-to)	2368-2373
Number of pages	6
Journal	Tetrahedron: Asymmetry
Volume	20
Issue number	20
DOIs	https://doi.org/10.1016/j.tetasy.2009.10.004
Publication status	Published - 20 Oct 2009

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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. https://doi.org/10.1016/j.tetasy.2009.10.004

Mercer, Thomas B. ; Jenkinson, Sarah F. ; Bartholomew, Barbara 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. In: Tetrahedron: Asymmetry. 2009 ; Vol. 20, No. 20. pp. 2368-2373.

@article{750936b2fff44a4eb4de8c4b20285645,

title = "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",

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 [K(i) = 0.13 mu M]-and LIL showed weak [K(i) = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K(i) = 64 mu M] and N-benzyl-LIL [K(i) = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase. ",

author = "Mercer, {Thomas B.} and Jenkinson, {Sarah F.} and Barbara Bartholomew and Nash, {Robert J.} and Saori Miyauchi and Atsushi Kato and Fleet, {George W. J.}",

year = "2009",

month = oct,

day = "20",

doi = "10.1016/j.tetasy.2009.10.004",

language = "English",

volume = "20",

pages = "2368--2373",

journal = "Tetrahedron: Asymmetry",

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Mercer, TB, Jenkinson, SF, Bartholomew, B, Nash, RJ, Miyauchi, S, Kato, A & Fleet, GWJ 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, vol. 20, no. 20, pp. 2368-2373. https://doi.org/10.1016/j.tetasy.2009.10.004

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, Thomas B.; Jenkinson, Sarah F.; Bartholomew, Barbara et al.
In: Tetrahedron: Asymmetry, Vol. 20, No. 20, 20.10.2009, p. 2368-2373.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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

AU - Mercer, Thomas B.

AU - Jenkinson, Sarah F.

AU - Bartholomew, Barbara

AU - Nash, Robert J.

AU - Miyauchi, Saori

AU - Kato, Atsushi

AU - Fleet, George W. J.

PY - 2009/10/20

Y1 - 2009/10/20

N2 - 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 [K(i) = 0.13 mu M]-and LIL showed weak [K(i) = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K(i) = 64 mu M] and N-benzyl-LIL [K(i) = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase.

AB - 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 [K(i) = 0.13 mu M]-and LIL showed weak [K(i) = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K(i) = 64 mu M] and N-benzyl-LIL [K(i) = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase.

U2 - 10.1016/j.tetasy.2009.10.004

DO - 10.1016/j.tetasy.2009.10.004

M3 - Article

SN - 0957-4166

VL - 20

SP - 2368

EP - 2373

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 20

ER -

Mercer TB, Jenkinson SF, Bartholomew B, Nash RJ, Miyauchi S, Kato A 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. 2009 Oct 20;20(20):2368-2373. doi: 10.1016/j.tetasy.2009.10.004