Enzymatic catalysis of the Diels-Alder reaction in the biosynthesis of natural products

被引:217
作者
Oikawa, H [1 ]
Tokiwano, T [1 ]
机构
[1] Hokkaido Univ, Div Chem, Grad Sch Sci, Kita Ku, Sapporo, Hokkaido 0600810, Japan
关键词
D O I
10.1039/b305068h
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
Recent studies on enzymes catalyzing the Diels-Alder reaction, often named "Diels-Alderases", clearly demonstrated the involvement of this synthetically useful reaction in the biosynthesis of natural products. This review covers natural Diels-Alder type cycloadducts, synthetic efforts on the chemical feasibility of the biosynthetic Diels-Alder reaction and a brief history of studies on Diels-Alderases. In addition, reaction mechanisms of artificial and natural Diets-Alderases are discussed.
引用
收藏
页码:321 / 352
页数:32
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共 300 条
[81]   TOTAL SYNTHESIS OF (-)-BETAENONE-C+ [J].
ICHIHARA, A ;
MIKI, S ;
KAWAGISHI, H ;
SAKAMURA, S .
TETRAHEDRON LETTERS, 1989, 30 (34) :4551-4554
[82]   ABSOLUTE-CONFIGURATION OF (-)-SOLANAPYRONE-A [J].
ICHIHARA, A ;
MIKI, M ;
SAKAMURA, S .
TETRAHEDRON LETTERS, 1985, 26 (20) :2453-2454
[83]   A PHYTOTOXIN, BETAENONE C, AND ITS RELATED METABOLITES OF PHOMA-BETAE FR [J].
ICHIHARA, A ;
OIKAWA, H ;
HASHIMOTO, M ;
SAKAMURA, S ;
HARAGUCHI, T ;
NAGANO, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1983, 47 (12) :2965-2967
[84]   STRUCTURES OF BETAENONE-A AND BETAENONE-B, NOVEL PHYTOTOXINS FROM PHOMA BETAE FR [J].
ICHIHARA, A ;
OIKAWA, H ;
HAYASHI, K ;
SAKAMURA, S ;
FURUSAKI, A ;
MATSUMOTO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2907-2908
[85]   SYNTHESIS OF (+)-SOLANAPYRONE-A [J].
ICHIHARA, A ;
MIKI, M ;
TAZAKI, H ;
SAKAMURA, S .
TETRAHEDRON LETTERS, 1987, 28 (11) :1175-1178
[86]  
Ichihara A, 1998, CURR ORG CHEM, V2, P365
[87]  
Ichihara A, 1999, COMPREHENSIVE NATURA, V1, P367
[88]   Tubelactomicin A, a novel 16-membered lactone antibiotic, from Nocardia sp.: I.: Taxonomy, production, isolation and biological properties [J].
Igarashi, M ;
Hayashi, C ;
Homma, Y ;
Hattori, S ;
Kinoshita, N ;
Hamada, M ;
Takeuchi, T .
JOURNAL OF ANTIBIOTICS, 2000, 53 (10) :1096-1101
[89]   Tubelactomicin A, a novel 16-membered lactone antibiotic, from Nocardia sp.: II.: Structure elucidation [J].
Igarashi, M ;
Nakamura, H ;
Naganawa, H ;
Takeuchi, T .
JOURNAL OF ANTIBIOTICS, 2000, 53 (10) :1102-1107
[90]  
IGUCHI K, 2003, P 45 S CHEM NAT PROD, P347