Synthesis of (±)-coronafacic acid

1977 ◽  
Vol 18 (49) ◽  
pp. 4331-4334 ◽  
Author(s):  
Akitami Ichihara ◽  
Ryoji Kimura ◽  
Koichi Moriyasu ◽  
Sadao Sakamura
Keyword(s):  
Coronafacic Acid

Similarities of the biological activities of coronatine and coronafacic acid to those of jasmonic acid

1996 ◽  
Vol 41 (1) ◽  
pp. 93-96 ◽  
Author(s):  
Yasunori Koda ◽  
Kiyoshi Takahashi ◽  
Yosio Kikuta ◽  
Friedemann Greulich ◽  
Hiroaki Toshima ◽  
...  
Keyword(s):  
Jasmonic Acid ◽  
Biological Activities ◽  
Coronafacic Acid

Total synthesis of d,l-coronafacic acid by an intermolecular Diels–Alder approach

1984 ◽  
Vol 62 (9) ◽  
pp. 1747-1750 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Montse Llinas-Brunet
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Keto Ester ◽  
Coronafacic Acid

An efficient total synthesis of d,l-coronafacic acid (2) has been achieved from 4-cyclopentene-1,3-dione (4). The synthesis involves keto ester 7 as a key intermediate that is conveniently prepared by the Diels–Alder addition of enedione 4 to ethyl 4-ethyl-2,4-pentadienoate (5).

ChemInform Abstract: Tandem Wessely Oxidation and Intramolecular Diels-Alder Reactions. Part 4. Synthesis of (.+-.)-Coronafacic Acid (XI).

ChemInform ◽  
2010 ◽  
Vol 24 (52) ◽  
pp. no-no
Author(s):  
P. YATES ◽  
N. K. BHAMARE ◽  
T. GRANGER ◽  
T. S. MACAS
Keyword(s):  
Diels Alder ◽  
Coronafacic Acid

scholarly journals Expedient Stereoselective Synthesis of Coronafacic Acid Through Intramolecular Diels—Alder Cyclization.

ChemInform ◽  
2007 ◽  
Vol 38 (26) ◽  
Author(s):  
Benoit Moreau ◽  
Maryon Ginisty ◽  
Dino Alberico ◽  
Andre B. Charette
Keyword(s):  
Stereoselective Synthesis ◽  
Diels Alder ◽  
Coronafacic Acid

Investigations of the biosynthesis of the phytotoxin coronatine

1994 ◽  
Vol 72 (1) ◽  
pp. 86-99 ◽  
Author(s):  
Ronald J. Parry ◽  
Sunil V. Mhaskar ◽  
Ming-Teh Lin ◽  
Alan E. Walker ◽  
Robson Mafoti
Keyword(s):  
Amino Acid ◽  
Pseudomonas Syringae ◽  
Cyclopropane Ring ◽  
Carbonyl Oxygen ◽  
Oxidative Cyclization ◽  
Amide Bond ◽  
Hydrogen Atoms ◽  
Coronafacic Acid ◽  
Polyketide Chain ◽  
Oxygen Atoms

The biosynthesis of the phytotoxin coronatine has been investigated by administration of isotopically labeled precursors to Pseudomonas syringae pv. glycinea. The structure of coronatine contains two moieties of distinct biosynthetic origin, a bicyclic, hydrindanone carboxylic acid (coronafacic acid) and a cyclopropyl α-amino acid (coronamic acid). Investigations of coronafacic acid biosynthesis have shown that this compound is a polyketide derived from three acetate units, one butyrate unit, and one pyruvate unit. The two carbonyl oxygen atoms of coronafacic acid were found to be derived from the oxygen atoms of acetate. Additional experiments are described that rule out some possible modes for assembly of the polyketide chain. Coronamic acid is shown to be derived from L-isoleucine via the intermediacy of L-alloisoleucine. Examination of the mechanism of the cyclization of L-alloisoleucine to coronamic acid revealed that the formation of the cyclopropane ring takes place with the removal of only two hydrogen atoms from the amino acid, one at C-2 and the other at C-6. The nitrogen atom at C-2 of L-alloisoleucine is shown to be retained. On the basis of these observations, a mechanism is postulated for the cyclization reaction that involves the diversion of an enzymatic hydroxylation reaction into an oxidative cyclization. Finally, a precursor incorporation experiment with deuterium-labeled coronamic acid demonstrated that free coronamic acid can be efficiently incorporated into coronatine. This observation indicates that the cyclization of L-alloisoleucine to coronamic acid can occur before formation of the amide bond between coronafacic acid and coronamic acid.

scholarly journals The structure-activity relationships in coronatine analogs and amino compounds derived from (+)-coronafacic acid.

1979 ◽  
Vol 43 (8) ◽  
pp. 1753-1757 ◽  
Author(s):  
Kunio SHIRAISHI ◽  
Keiichi KONOMA ◽  
Hiroji SATO ◽  
Akitami ICHIHARA ◽  
Sadao SAKAMURA ◽  
...  
Keyword(s):  
Structure Activity Relationships ◽  
Coronafacic Acid ◽  
Structure Activity ◽  
Amino Compounds

scholarly journals Pseudomonas syringae pv. tomato DC3000 CmaL (PSPTO4723), a DUF1330 Family Member, Is Needed To Produce l-allo-Isoleucine, a Precursor for the Phytotoxin Coronatine

2012 ◽  
Vol 195 (2) ◽  
pp. 287-296 ◽  
Author(s):  
Jay N. Worley ◽  
Alistair B. Russell ◽  
Aaron G. Wexler ◽  
Philip A. Bronstein ◽  
Brian H. Kvitko ◽  
...  
Keyword(s):  
Pseudomonas Syringae ◽  
Genomic Region ◽  
Tomato Dc3000 ◽  
Content Type ◽  
Type Iii Effectors ◽  
Type Iii ◽  
Coronafacic Acid ◽  
Feeding Experiments ◽  
Leaf Chlorosis

ABSTRACTPseudomonas syringaepv. tomato DC3000 produces the phytotoxin coronatine, a major determinant of the leaf chlorosis associated with DC3000 pathogenesis. The DC3000 PSPTO4723 (cmaL) gene is located in a genomic region encoding type III effectors; however, it promotes chlorosis in the model plantNicotiana benthamianain a manner independent of type III secretion. Coronatine is produced by the ligation of two moieties, coronafacic acid (CFA) and coronamic acid (CMA), which are produced by biosynthetic pathways encoded in separate operons. Cross-feeding experiments, performed inN. benthamianawithcfa,cma, andcmaLmutants, implicate CmaL in CMA production. Furthermore, analysis of bacterial supernatants under coronatine-inducing conditions revealed that mutants lacking either thecmaoperon orcmaLaccumulate CFA rather than coronatine, supporting a role for CmaL in the regulation or biosynthesis of CMA. CmaL does not appear to regulate CMA production, since the expression of proteins with known roles in CMA production is unaltered incmaLmutants. Rather, CmaL is needed for the first step in CMA synthesis, as evidenced by the fact that wild-type levels of coronatine production are restored to a ΔcmaLmutant when it is supplemented with 50 μg/mll-allo-isoleucine, the starting unit for CMA production.cmaLis found in all other sequencedP. syringaestrains with coronatine biosynthesis genes. This characterization of CmaL identifies a critical missing factor in coronatine production and provides a foundation for further investigation of a member of the widespread DUF1330 protein family.

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