Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine

AE Hakansson; J van Ameijde; G Horne; RJ Nash; MR Wormald; A Kato; Gurdyal Besra; Sudagar Gurcha; GWJ Fleet

doi:10.1016/j.tetlet.2007.10.142

Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine

AE Hakansson, J van Ameijde, G Horne, RJ Nash, MR Wormald, A Kato, Gurdyal Besra, Sudagar Gurcha, GWJ Fleet

Biosciences

Research output: Contribution to journal › Article

41 Citations (Scopus)

Abstract

Efficient syntheses are reported of the alpha-L-rhamnosidase inhibitors L-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine1,2,8-triol], (6R)-C-methyl-L-swainsonine (IR,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-L-swainsonine (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(IR,2S, 6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl- L-swainsonine [K-i=0.032 mu M] is a significantly more potent naringinase inhibitor than L-swainsonine [K-i = 0.45 mu M]. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	179-184
Number of pages	6
Journal	Tetrahedron Letters
Volume	49
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2007.10.142
Publication status	Published - 1 Jan 2008

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Hakansson, AE., van Ameijde, J., Horne, G., Nash, RJ., Wormald, MR., Kato, A., Besra, G., Gurcha, S., & Fleet, GWJ. (2008). Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine. Tetrahedron Letters, 49(1), 179-184. https://doi.org/10.1016/j.tetlet.2007.10.142

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title = "Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine",

abstract = "Efficient syntheses are reported of the alpha-L-rhamnosidase inhibitors L-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine1,2,8-triol], (6R)-C-methyl-L-swainsonine (IR,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-L-swainsonine (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(IR,2S, 6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl- L-swainsonine [K-i=0.032 mu M] is a significantly more potent naringinase inhibitor than L-swainsonine [K-i = 0.45 mu M]. (c) 2007 Elsevier Ltd. All rights reserved.",

author = "AE Hakansson and {van Ameijde}, J and G Horne and RJ Nash and MR Wormald and A Kato and Gurdyal Besra and Sudagar Gurcha and GWJ Fleet",

year = "2008",

month = jan,

day = "1",

doi = "10.1016/j.tetlet.2007.10.142",

language = "English",

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Hakansson, AE, van Ameijde, J, Horne, G, Nash, RJ, Wormald, MR, Kato, A, Besra, G , Gurcha, S & Fleet, GWJ 2008, 'Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine', Tetrahedron Letters, vol. 49, no. 1, pp. 179-184. https://doi.org/10.1016/j.tetlet.2007.10.142

Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine. / Hakansson, AE; van Ameijde, J; Horne, G et al.
In: Tetrahedron Letters, Vol. 49, No. 1, 01.01.2008, p. 179-184.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine

AU - Hakansson, AE

AU - van Ameijde, J

AU - Horne, G

AU - Nash, RJ

AU - Wormald, MR

AU - Kato, A

AU - Besra, Gurdyal

AU - Gurcha, Sudagar

AU - Fleet, GWJ

PY - 2008/1/1

Y1 - 2008/1/1

N2 - Efficient syntheses are reported of the alpha-L-rhamnosidase inhibitors L-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine1,2,8-triol], (6R)-C-methyl-L-swainsonine (IR,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-L-swainsonine (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(IR,2S, 6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl- L-swainsonine [K-i=0.032 mu M] is a significantly more potent naringinase inhibitor than L-swainsonine [K-i = 0.45 mu M]. (c) 2007 Elsevier Ltd. All rights reserved.

AB - Efficient syntheses are reported of the alpha-L-rhamnosidase inhibitors L-swainsonine [(1R,2S,8S,8aS)-octahydroindolizine1,2,8-triol], (6R)-C-methyl-L-swainsonine (IR,2S,6R,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol, (6S)-C-methyl-L-swainsonine (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol and related 6-C-methyl hydroxycastanospermines [(IR,2S, 6R,7R,8R,8aR)-6-methyl-octahydroindolizine-1,2,6,7,8-pentaol and (IR,2S,6S,8S,8aS)-6-methyloctahydro-indolizine-1,2,8-triol]. (6R)-C-Methyl- L-swainsonine [K-i=0.032 mu M] is a significantly more potent naringinase inhibitor than L-swainsonine [K-i = 0.45 mu M]. (c) 2007 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2007.10.142

DO - 10.1016/j.tetlet.2007.10.142

M3 - Article

VL - 49

SP - 179

EP - 184

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Hakansson AE, van Ameijde J, Horne G, Nash RJ, Wormald MR, Kato A et al. Synthesis of the naringinase inhibitors L-swainsonine and related 6-C-methyl-L-swainsonine analogues: (6R)-C-methyl-L-swainsonine is a more potent inhibitor of L-rhamnosidase by an order of magnitude than L-swainsonine. Tetrahedron Letters. 2008 Jan 1;49(1):179-184. doi: 10.1016/j.tetlet.2007.10.142