Enantiomeric Natural Products: Occurrence and Biogenesis

被引:230
作者
Finefield, Jennifer M. [1 ]
Sherman, David H. [2 ,3 ,4 ,6 ]
Kreitman, Martin [5 ]
Williams, Robert M. [1 ,7 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[2] Univ Michigan, Inst Life Sci, Ann Arbor, MI 48109 USA
[3] Univ Michigan, Dept Med Chem, Ann Arbor, MI 48109 USA
[4] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
[5] Univ Chicago, Dept Ecol & Evolut, Chicago, IL 60637 USA
[6] Univ Michigan, Dept Microbiol & Immunol, Ann Arbor, MI 48109 USA
[7] Univ Colorado, Ctr Canc, Aurora, CO 80045 USA
基金
美国国家卫生研究院;
关键词
biosynthesis; enantioselectivity; isolation; natural products; STREPTOMYCES-COELICOLOR A3(2); PRENYLATED INDOLE ALKALOIDS; BIOSYNTHETIC GENE-CLUSTER; SAGE SALVIA-OFFICINALIS; MARINE-DERIVED FUNGUS; PYRAN RING FORMATION; FIR ABIES-GRANDIS; MEDICAGO-SATIVA L; SPONGE-IRCINIA SP; CDNA ISOLATION;
D O I
10.1002/anie.201107204
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In nature, chiral natural products are usually produced in optically pure formhowever, occasionally both enantiomers are formed. These enantiomeric natural products can arise from a single species or from different genera and/or species. Extensive research has been carried out over the years in an attempt to understand the biogenesis of naturally occurring enantiomers; however, many fascinating puzzles and stereochemical anomalies still remain.
引用
收藏
页码:4802 / 4836
页数:35
相关论文
共 338 条
[41]   Synergy and contingency as driving forces for the evolution of multiple secondary metabolite production by Streptomyces species [J].
Challis, GL ;
Hopwood, DA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2003, 100 :14555-14561
[42]   AEGELINOL, A MINOR LACTONIC CONSTITUENT OF AEGLE-MARMELOS [J].
CHATTERJEE, A ;
SEN, R ;
GANGULY, D .
PHYTOCHEMISTRY, 1978, 17 (02) :328-329
[43]   Optimized conditions for the extraction of secondary volatile metabolites in Angelica roots by accelerated solvent extraction [J].
Cho, S.-K. ;
Abd El-Aty, A. M. ;
Choi, J.-H. ;
Kim, M. R. ;
Shim, J. H. .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2007, 44 (05) :1154-1158
[44]   Antinociceptive mechanisms of orally administered decursinol in the mouse [J].
Choi, SS ;
Han, KJ ;
Lee, JK ;
Lee, HK ;
Han, EJ ;
Kim, DH ;
Suh, HW .
LIFE SCIENCES, 2003, 73 (04) :471-485
[45]  
CIMINO G, 1975, TETRAHEDRON LETT, P1425
[46]   ENT-CHROMAZONAROL, A CHROMAN-SESQUITERPENOID FROM SPONGE DISIDEA-PALLESCENS [J].
CIMINO, G ;
DESTEFANO, S ;
MINALE, L .
EXPERIENTIA, 1975, 31 (10) :1117-1118
[47]   Lessons from natural molecules [J].
Clardy, J ;
Walsh, C .
NATURE, 2004, 432 (7019) :829-837
[48]   Germacrene C synthase from Lycopersicon esculentum cv. VFNT Cherry tomato:: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase [J].
Colby, SM ;
Crock, J ;
Dowdle-Rizzo, B ;
Lemaux, PG ;
Croteau, R .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (05) :2216-2221
[49]  
COLBY SM, 1993, J BIOL CHEM, V268, P23016
[50]   BIOSYNTHESIS OF THE ANTIBIOTIC ACTINORHODIN - ANALYSIS OF BLOCKED MUTANTS OF STREPTOMYCES-COELICOLOR [J].
COLE, SP ;
RUDD, BAM ;
HOPWOOD, DA ;
CHANG, CJ ;
FLOSS, HG .
JOURNAL OF ANTIBIOTICS, 1987, 40 (03) :340-347