The selective enzymatic synthesis of lipophilic esters of swainsonine

Gabriel G. Perrone; Kevin D. Barrow; Ian J. McFarlane

doi:10.1016/S0968-0896(98)00271-5

The selective enzymatic synthesis of lipophilic esters of swainsonine

Gabriel G. Perrone, Kevin D. Barrow, Ian J. McFarlane

University of New South Wales

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

13 Citations (Scopus)

Abstract

The potent and specific inhibitor of Golgi α-mannosidase II, swainsonine (SW) has been isolated in high yield from Swainsona procumbens and derivatised by regiospecific enzymatic reactions. In this study the regioselectivity of three commercially available enzymes, subtilisin Carlsberg, porcine pancreatic lipase (PPL) and Candida cylindracea lipase was determined for the acylation of swainsonine in predominantly anhydrous organic medium. The use of subtilisin in pyridine facilitated the single step synthesis of 2-O-butyryl-SW in a 23% yield, whilst catalysis by PPL in tetrahydrofuran gave 2-O-butyryl-SW (6%) and 1,2-di-O-butyryl-SW (31%). Copyright (C) 1999 Elsevier Science Ltd.

Original language	English
Pages (from-to)	831-835
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	7
Issue number	5
DOIs	https://doi.org/10.1016/S0968-0896(98)00271-5
Publication status	Published - May 1999
Externally published	Yes

Keywords

Enzymatic synthesis
Mannosidase inhibitor
Regioselective synthesis
Swainsona procumbens
Swainsonine

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10.1016/S0968-0896(98)00271-5

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title = "The selective enzymatic synthesis of lipophilic esters of swainsonine",

abstract = "The potent and specific inhibitor of Golgi α-mannosidase II, swainsonine (SW) has been isolated in high yield from Swainsona procumbens and derivatised by regiospecific enzymatic reactions. In this study the regioselectivity of three commercially available enzymes, subtilisin Carlsberg, porcine pancreatic lipase (PPL) and Candida cylindracea lipase was determined for the acylation of swainsonine in predominantly anhydrous organic medium. The use of subtilisin in pyridine facilitated the single step synthesis of 2-O-butyryl-SW in a 23% yield, whilst catalysis by PPL in tetrahydrofuran gave 2-O-butyryl-SW (6%) and 1,2-di-O-butyryl-SW (31%). Copyright (C) 1999 Elsevier Science Ltd.",

keywords = "Enzymatic synthesis, Mannosidase inhibitor, Regioselective synthesis, Swainsona procumbens, Swainsonine",

author = "Perrone, {Gabriel G.} and Barrow, {Kevin D.} and McFarlane, {Ian J.}",

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T1 - The selective enzymatic synthesis of lipophilic esters of swainsonine

AU - Perrone, Gabriel G.

AU - Barrow, Kevin D.

AU - McFarlane, Ian J.

PY - 1999/5

Y1 - 1999/5

N2 - The potent and specific inhibitor of Golgi α-mannosidase II, swainsonine (SW) has been isolated in high yield from Swainsona procumbens and derivatised by regiospecific enzymatic reactions. In this study the regioselectivity of three commercially available enzymes, subtilisin Carlsberg, porcine pancreatic lipase (PPL) and Candida cylindracea lipase was determined for the acylation of swainsonine in predominantly anhydrous organic medium. The use of subtilisin in pyridine facilitated the single step synthesis of 2-O-butyryl-SW in a 23% yield, whilst catalysis by PPL in tetrahydrofuran gave 2-O-butyryl-SW (6%) and 1,2-di-O-butyryl-SW (31%). Copyright (C) 1999 Elsevier Science Ltd.

AB - The potent and specific inhibitor of Golgi α-mannosidase II, swainsonine (SW) has been isolated in high yield from Swainsona procumbens and derivatised by regiospecific enzymatic reactions. In this study the regioselectivity of three commercially available enzymes, subtilisin Carlsberg, porcine pancreatic lipase (PPL) and Candida cylindracea lipase was determined for the acylation of swainsonine in predominantly anhydrous organic medium. The use of subtilisin in pyridine facilitated the single step synthesis of 2-O-butyryl-SW in a 23% yield, whilst catalysis by PPL in tetrahydrofuran gave 2-O-butyryl-SW (6%) and 1,2-di-O-butyryl-SW (31%). Copyright (C) 1999 Elsevier Science Ltd.

KW - Enzymatic synthesis

KW - Mannosidase inhibitor

KW - Regioselective synthesis

KW - Swainsona procumbens

KW - Swainsonine

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U2 - 10.1016/S0968-0896(98)00271-5

DO - 10.1016/S0968-0896(98)00271-5

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AN - SCOPUS:0033135759

SN - 0968-0896

VL - 7

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EP - 835

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 5

ER -

The selective enzymatic synthesis of lipophilic esters of swainsonine

Abstract

Keywords

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