Concise synthesis of artemisinin from a farnesyl diphosphate analogue

被引：24

作者：

Tang, Xiaoping ^{[1
]}

Demiray, Melodi ^{[1
]}

Wirth, Thomas ^{[1
]}

Allemann, Rudolf K. ^{[1
]}

机构：

[1] Cardiff Univ, Sch Chem, Pk Pl,Main Bldg, Cardiff CF10 3AT, S Glam, Wales

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2018年 / 26卷 / 07期

基金：

英国生物技术与生命科学研究理事会; 英国工程与自然科学研究理事会;

关键词：

Malaria; Artemisinin; Amorphadiene synthase; Dihydroartemisinic aldehyde; Dihydroartemisinic acid; Farnesyl diphosphate; ANTIMALARIAL-DRUG; AMORPHA-4,11-DIENE SYNTHASE; DIHYDROARTEMISINIC ACID; QINGHAOSU ARTEMISININ; MALARIA DRUG; CYCLIZATION; CONVERSION; MECHANISM; 5-EPI-ARISTOLOCHENE; PRECURSOR;

D O I：

10.1016/j.bmc.2017.03.068

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Artemisinin is one of the most potent anti-malaria drugs and many often-lengthy routes have been developed for its synthesis. Amorphadiene synthase, a key enzyme in the biosynthetic pathway of artemisinin, is able to convert an oxygenated farnesyl diphosphate analogue directly to dihydroartemisinic aldehyde, which can be converted to artemisinin in only four chemical steps, resulting in an efficient synthetic route to the anti-malaria drug. (C) 2017 The Authors. Published by Elsevier Ltd.

引用

页码：1314 / 1319

页数：6

共 50 条

[1] ON THE CONVERSION OF DIHYDROARTEMISINIC ACID INTO ARTEMISININ [J].

ACTON, N ;

ROTH, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3610-3614

[2]

Amara Z, 2015, NAT CHEM, V7, P489, DOI [10.1038/NCHEM.2261, 10.1038/nchem.2261]

[3]

[Anonymous], TRENDS PARASITOL, DOI DOI 10.1172/JCI200421682

[4]

BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3

[5] ENZYMATIC FORMATION OF SESQUITERPENES [J].

CANE, DE .

CHEMICAL REVIEWS, 1990, 90 (07) :1089-1103

[6] Efficient Terpene Synthase Catalysis by Extraction in Flow [J].

Cascon, Oscar ;

Richter, Gerald ;

Allemann, Rudolf K. ;

Wirth, Thomas .

CHEMPLUSCHEM, 2013, 78 (11) :1334-1337

[7] Chemoenzymatic preparation of germacrene analogues [J].

Cascon, Oscar ;

Touchet, Sabrina ;

Miller, David J. ;

Gonzalez, Veronica ;

Faraldos, Juan A. ;

Allemann, Rudolf K. .

CHEMICAL COMMUNICATIONS, 2012, 48 (78) :9702-9704

[8] Making artemisinin [J].

Covello, Patrick S. .

PHYTOCHEMISTRY, 2008, 69 (17) :2881-2885

[9] PHOSPHORYLATION OF ISOPRENOID ALCOHOLS [J].

DAVISSON, VJ ;

WOODSIDE, AB ;

NEAL, TR ;

STREMLER, KE ;

MUEHLBACHER, M ;

POULTER, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4768-4779

[10] An Efficient Chemoenzymatic Synthesis of Dihydroartemisinic Aldehyde [J].

Demiray, Melodi ;

Tang, Xiaoping ;

Wirth, Thomas ;

Faraldos, Juan A. ;

Allemann, Rudolf K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) :4347-4350

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