Enantiomeric Natural Products: Occurrence and Biogenesis

被引:226
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
  • [11] BIOSYNTHESIS OF THE MACROTETROLIDE ANTIBIOTICS - THE INCORPORATION OF C-13 AND O-18 LABELED ACETATE, PROPIONATE, AND SUCCINATE
    ASHWORTH, DM
    ROBINSON, JA
    TURNER, DL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1719 - 1727
  • [12] ON THE BIOSYNTHETIC ORIGINS OF THE HYDROGEN-ATOMS IN THE MACROTETROLIDE ANTIBIOTICS - AND THEIR MODE OF ASSEMBLY CATALYZED BY A NONACTIN POLYKETIDE SYNTHASE
    ASHWORTH, DM
    CLARK, CA
    ROBINSON, JA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08): : 1461 - 1467
  • [13] Orange/lemon-scented beetles: opposite enantiomers of limonene as major constituents in the defensive secretion of related carabids
    Attygalle, Athula B.
    Wu, Xiaogang
    Maddison, David R.
    Will, Kipling W.
    [J]. NATURWISSENSCHAFTEN, 2009, 96 (12) : 1443 - 1449
  • [14] Bae FA, 1998, BIOL PHARM BULL, V21, P990, DOI 10.1248/bpb.21.990
  • [15] Baerson S. R., 2005, ACS SYM SER, V995, P2
  • [16] TERPENE BIOSYNTHESIS .3. BIOSYNTHESIS OF (+)-CAMPHOR AND (-)-CAMPHOR IN ARTEMISIA, SALVIA, AND CHRYSANTHEMUM SPECIES
    BANTHROP.DV
    BAXENDAL.D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (19): : 2694 - &
  • [17] Antimicrobial and Antioxidant Activities of Coumarins from the Roots of Ferulago campestris (Apiaceae)
    Basile, Adriana
    Sorbo, Sergio
    Spadaro, Vivienne
    Bruno, Maurizio
    Maggio, Antonella
    Faraone, Nicoletta
    Rosselli, Sergio
    [J]. MOLECULES, 2009, 14 (03): : 939 - 952
  • [18] BIOSYNTHESIS .19. CONCERNING BIOSYNTHESIS OF (-)-CAMPHOR AND (-)-BORNEOL IN SALVIA-OFFICINALIS
    BATTERSBY, AR
    LAING, DG
    RAMAGE, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (21): : 2743 - +
  • [19] FORMATION OF (R)-CONFIGURATED TETRAHYDROPROTOBERBERINE ALKALOIDS INVIVO AND INVITRO
    BAUER, W
    ZENK, MH
    [J]. TETRAHEDRON LETTERS, 1991, 32 (04) : 487 - 490
  • [20] Antibacterial metabolites from Australian macrofungi from the genus Cortinarius
    Beattie, Karren D.
    Rouf, Razina
    Gander, Louisa
    May, Tom W.
    Ratkowsky, David
    Donner, Christopher D.
    Gill, Melvyn
    Grice, I. Darren
    Tiralongo, Evelin
    [J]. PHYTOCHEMISTRY, 2010, 71 (8-9) : 948 - 955