Total Synthesis of a Reported Fluorometabolite from Streptomyces sp TC1 Indicates an Incorrect Assignment. The Isolated Compound Did Not Contain Fluorine

被引:14
作者
Ayoup, Mohammed Salah [1 ,2 ]
Cordes, David B. [1 ]
Slawin, Alexandra M. Z. [1 ]
O'Hagan, David [1 ]
机构
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Alexandria, Fac Sci, Dept Chem, Ibrahimia, Egypt
来源
JOURNAL OF NATURAL PRODUCTS | 2014年 / 77卷 / 06期
基金
英国生物技术与生命科学研究理事会;
关键词
ANTIOXIDANTS; ACCEPTOR; POTENT;
D O I
10.1021/np500260z
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
3,5-Di-tert-butyl-4-fluorophenylpropionic acid (1) was recently reported as a natural product from Streptomyces sp. TC1. This was a notable disclosure because fluorinated natural products are exceedingly rare, and in this case it suggested that the bacterium had the capacity to mediate an enzymatic aryl fluorination reaction. However, a synthesis of the putative metabolite 1 demonstrates that the spectroscopic data are inconsistent with the proposed structure. There is no evidence that the isolated compound contained a fluorine atom.
引用
收藏
页码:1249 / 1251
页数:3
相关论文
共 17 条
  • [1] 3,5-disubstituted-4-hydroxyphenyls linked to 3-hydroxy-2-methyl-4(1H)-pyridinone:: Potent inhibitors of lipid peroxidation and cell toxicity
    Bebbington, D
    Monck, NJT
    Gaur, S
    Palmer, AM
    Benwell, K
    Harvey, V
    Malcolm, CS
    Porter, RHP
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (15) : 2779 - 2782
  • [2] Immobilization of antioxidants via ADMET polymerization for enhanced long-term stabilization of polyolefins
    Beer, Stephan
    Teasdale, Ian
    Brueggemann, Oliver
    [J]. EUROPEAN POLYMER JOURNAL, 2013, 49 (12) : 4257 - 4264
  • [3] VAN DER WAALS VOLUMES + RADII
    BONDI, A
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) : 441 - +
  • [4] Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach
    Chavan, Subhash P.
    Khatod, Harshali S.
    [J]. TETRAHEDRON-ASYMMETRY, 2012, 23 (18-19) : 1410 - 1415
  • [5] G W., 1985, TETRAHEDRON LETT, V26, P3779
  • [6] Intramolecular OH•••FC Hydrogen Bonding in Fluorinated Carbohydrates: CHF is a Better Hydrogen Bond Acceptor than CF2
    Giuffredi, Guy T.
    Gouverneur, Veronique
    Bernet, Bruno
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) : 10524 - 10528
  • [7] THE FLUORINATED NATURAL-PRODUCTS
    HARPER, DB
    OHAGAN, D
    [J]. NATURAL PRODUCT REPORTS, 1994, 11 (02) : 123 - 133
  • [8] Hill R. A., 2014, NAT PROD REP, V31, P414
  • [9] Natural Occurrence of Organofluorine and Other Constituents from Streptomyces sp TC1
    Jaivel, Nanjundan
    Uvarani, Chokkalingam
    Rajesh, Ramasamy
    Velmurugan, Devadasan
    Marimuthu, Ponnusamy
    [J]. JOURNAL OF NATURAL PRODUCTS, 2014, 77 (01): : 2 - 8
  • [10] Dual role of phenols as fragrances and antioxidants: mechanism, kinetics and drastic solvent effect
    Marteau, Clementine
    Nardello-Rataj, Veronique
    Favier, Dominique
    Aubry, Jean-Marie
    [J]. FLAVOUR AND FRAGRANCE JOURNAL, 2013, 28 (01) : 30 - 38