Natural Diels-Alderases: Elusive and Irresistable

被引：89

作者：

Klas, Kimberly ^{[1
]}

Tsukamoto, Sachiko ^{[2
]}

Sherman, David H. ^{[3
,4
,5
,6
]}

Williams, Robert M. ^{[1
,7
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80524 USA

[2] Kumamoto Univ, Grad Sch Pharmaceut Sci, Kumamoto 8620973, Japan

[3] Univ Michigan, Inst Life Sci, Ann Arbor, MI 48109 USA

[4] Univ Michigan, Dept Med Chem, Ann Arbor, MI 48109 USA

[5] Univ Michigan, Dept Microbiol & Immunol, Ann Arbor, MI 48109 USA

[6] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

[7] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 23期

基金：

美国国家卫生研究院;

关键词：

TRANSITION-STATES; MACROPHOMATE SYNTHASE; SOLANAPYRONE SYNTHASE; STEPWISE MECHANISMS; ENZYMATIC-ACTIVITY; BIOSYNTHESIS; CATALYSIS; CYCLOADDITION; BUTADIENE; ETHYLENE;

D O I：

10.1021/acs.joc.5b01951

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Eight examples of biosynthetic pathways wherein a natural enzyme has been identified and claimed to function as a catalyst for the [4 + 2] cycloaddition reaction, namely, Diels-Alderases, are briefly reviewed. These are discussed in the context of the mechanistic challenges associated with the technical difficulty of proving that the net formal [4 + 2] cydoaddition under study indeed proceeds through a synchronous mechanism and that the putative biosynthetic enzyme deploys the pericyclic transition state required for a Diels-Alder cycloaddition reaction.

引用

页码：11672 / 11685

页数：14

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