Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

Ahmad Ghavami; Blair D. Johnston; Matthew D. Maddess; Sarah M. Chinapoo; Morten T. Jensen; Birte Svensson; B. Mario Pinto

doi:10.1139/V02-078

Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

Ahmad Ghavami, Blair D. Johnston, Matthew D. Maddess, Sarah M. Chinapoo, Morten T. Jensen, Birte Svensson, B. Mario Pinto

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-Xylitol at the least-hindered carbon of 2,4- O-benzylidene-L-erythritol-1, 3 -cyclic sulfate. The sulfonium ion 8 inhibited barley-alpha-amylase (AMY1) and porcine pancreatic-alpha-amylase (PPA), with K-i values of 109 +/- 11 and 55 +/- 5 muM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.

Original language	English
Journal	Canadian Journal of Chemistry
Volume	80
Issue number	8
Pages (from-to)	932-947
ISSN	0008-4042
DOIs	https://doi.org/10.1139/V02-078
Publication status	Published - 2002
Externally published	Yes

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@article{1d63cd979d304e7b950329132545d9c1,

title = "Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors",

abstract = "The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-Xylitol at the least-hindered carbon of 2,4- O-benzylidene-L-erythritol-1, 3 -cyclic sulfate. The sulfonium ion 8 inhibited barley-alpha-amylase (AMY1) and porcine pancreatic-alpha-amylase (PPA), with K-i values of 109 +/- 11 and 55 +/- 5 muM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase. ",

author = "Ahmad Ghavami and Johnston, {Blair D.} and Maddess, {Matthew D.} and Chinapoo, {Sarah M.} and Jensen, {Morten T.} and Birte Svensson and Pinto, {B. Mario}",

year = "2002",

doi = "10.1139/V02-078",

language = "English",

volume = "80",

pages = "932--947",

journal = "Canadian Journal of Chemistry",

issn = "0008-4042",

publisher = "NRC Research Press",

number = "8",

}

Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors. / Ghavami, Ahmad; Johnston, Blair D.; Maddess, Matthew D. et al.
In: Canadian Journal of Chemistry, Vol. 80, No. 8, 2002, p. 932-947.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

AU - Ghavami, Ahmad

AU - Johnston, Blair D.

AU - Maddess, Matthew D.

AU - Chinapoo, Sarah M.

AU - Jensen, Morten T.

AU - Svensson, Birte

AU - Pinto, B. Mario

PY - 2002

Y1 - 2002

N2 - The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-Xylitol at the least-hindered carbon of 2,4- O-benzylidene-L-erythritol-1, 3 -cyclic sulfate. The sulfonium ion 8 inhibited barley-alpha-amylase (AMY1) and porcine pancreatic-alpha-amylase (PPA), with K-i values of 109 +/- 11 and 55 +/- 5 muM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.

AB - The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-Xylitol at the least-hindered carbon of 2,4- O-benzylidene-L-erythritol-1, 3 -cyclic sulfate. The sulfonium ion 8 inhibited barley-alpha-amylase (AMY1) and porcine pancreatic-alpha-amylase (PPA), with K-i values of 109 +/- 11 and 55 +/- 5 muM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.

U2 - 10.1139/V02-078

DO - 10.1139/V02-078

M3 - Journal article

SN - 0008-4042

VL - 80

SP - 932

EP - 947

JO - Canadian Journal of Chemistry

JF - Canadian Journal of Chemistry

IS - 8

ER -

Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally-occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

Abstract

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