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 [J].
Bebbington, D ;
Monck, NJT ;
Gaur, S ;
Palmer, AM ;
Benwell, K ;
Harvey, V ;
Malcolm, CS ;
Porter, RHP .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (15) :2779-2782
[2]   Immobilization of antioxidants via ADMET polymerization for enhanced long-term stabilization of polyolefins [J].
Beer, Stephan ;
Teasdale, Ian ;
Brueggemann, Oliver .
EUROPEAN POLYMER JOURNAL, 2013, 49 (12) :4257-4264
[3]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
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 [J].
Chavan, Subhash P. ;
Khatod, Harshali S. .
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 [J].
Giuffredi, Guy T. ;
Gouverneur, Veronique ;
Bernet, Bruno .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) :10524-10528
[7]   THE FLUORINATED NATURAL-PRODUCTS [J].
HARPER, DB ;
OHAGAN, D .
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 [J].
Jaivel, Nanjundan ;
Uvarani, Chokkalingam ;
Rajesh, Ramasamy ;
Velmurugan, Devadasan ;
Marimuthu, Ponnusamy .
JOURNAL OF NATURAL PRODUCTS, 2014, 77 (01) :2-8
[10]   Dual role of phenols as fragrances and antioxidants: mechanism, kinetics and drastic solvent effect [J].
Marteau, Clementine ;
Nardello-Rataj, Veronique ;
Favier, Dominique ;
Aubry, Jean-Marie .
FLAVOUR AND FRAGRANCE JOURNAL, 2013, 28 (01) :30-38