The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

被引:60
作者
Lin, Chia-I. [1 ,2 ]
McCarty, Reid M. [1 ,2 ]
Liu, Hung-wen [1 ,2 ]
机构
[1] Univ Texas Austin, Div Chem Biol & Med Chem, Coll Pharm, Austin, TX 78731 USA
[2] Univ Texas Austin, Dept Chem, Austin, TX 78731 USA
基金
美国国家卫生研究院;
关键词
biosynthesis; catalysis; enzymes; name reaction; reaction mechanisms; ANAEROBIC BENZOATE DEGRADATION; METHYLERYTHRITOL PHOSPHATE-PATHWAY; PHENYLALANINE AMMONIA-LYASE; CATALYZED 4+2 CYCLOADDITION; BAEYER-VILLIGER OXIDATION; BIOSYNTHETIC GENE-CLUSTER; DIELS-ALDER REACTION; INDUCED DNA CLEAVAGE; POLYKETIDE SYNTHASE; STRICTOSIDINE SYNTHASE;
D O I
10.1002/anie.201603291
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chemical reactions that are named in honor of their true, or at least perceived, discoverers are known as "name reactions". This Review is a collection of biological representatives of named chemical reactions. Emphasis is placed on reaction types and catalytic mechanisms that showcase both the chemical diversity in natural product biosynthesis as well as the parallels with synthetic organic chemistry. An attempt has been made, whenever possible, to describe the enzymatic mechanisms of catalysis within the context of their synthetic counterparts and to discuss the mechanistic hypotheses for those reactions that are currently active areas of investigation. This Review has been categorized by reaction type, for example condensation, nucleophilic addition, reduction and oxidation, substitution, carboxylation, radical-mediated, and rearrangements, which are subdivided by name reactions.
引用
收藏
页码:3446 / 3489
页数:44
相关论文
共 416 条
[81]   Specificity and Reactivity in Menaquinone Biosynthesis: The Structure of Escherichia coli MenD (2-Succinyl-5-Enolpyruvyl-6-Hydroxy-3-Cyclohexadiene-1-Carboxylate Synthase) [J].
Dawson, Alice ;
Fyfe, Paul K. ;
Hunter, William N. .
JOURNAL OF MOLECULAR BIOLOGY, 2008, 384 (05) :1353-1368
[82]   Purification and characterization of deacetylipecoside synthase from Alangium lamarckii Thw. [J].
De-Eknamkul, W ;
Suttipanta, N ;
Kutchan, TM .
PHYTOCHEMISTRY, 2000, 55 (02) :177-181
[83]   CHARACTERIZATION OF THE INVITRO CYCLIZATION CHEMISTRY OF CALICHEAMICIN AND ITS RELATION TO DNA CLEAVAGE [J].
DEVOSS, JJ ;
HANGELAND, JJ ;
TOWNSEND, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4554-4556
[84]   STRUCTURE OF STIPITATIC ACID [J].
DEWAR, MJS .
NATURE, 1945, 155 (3924) :50-51
[85]  
Dewick P., 2002, Medicinal Natural Products. A Biosynthetic Approach
[86]  
Dieckmann W., 1894, CHEM BER-RECL, V27, P102, DOI DOI 10.1002/CBER.18940270126
[87]   Coping with toxic plant compounds - The insect's perspective on iridoid glycosides and cardenolides [J].
Dobler, Susanne ;
Petschenka, Georg ;
Pankoke, Helga .
PHYTOCHEMISTRY, 2011, 72 (13) :1593-1604
[88]   A global assembly line for cyanobactins [J].
Donia, Mohamed S. ;
Ravel, Jacques ;
Schmidt, Eric W. .
NATURE CHEMICAL BIOLOGY, 2008, 4 (06) :341-343
[89]   PURIFICATION AND PROPERTIES OF CYCLOHEXANONE OXYGENASE FROM NOCARDIA-GLOBERULA CL1 AND ACINETOBACTER NCIB-9871 [J].
DONOGHUE, NA ;
NORRIS, DB ;
TRUDGILL, PW .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1976, 63 (01) :175-192
[90]   The biosynthesis of the thiazole phosphate moiety of thiamin (Vitamin B1):: The early steps catalyzed by thiazole synthase [J].
Dorrestein, PC ;
Zhai, HL ;
Taylor, SV ;
McLafferty, FW ;
Begley, TP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3091-3096