Synthesis of (R)- and (S)-10,16-dihydroxyhexadecanoic acid: Cutin stereochemistry and fungal activation

Phytochemistry

Volumn 63, Issue 1, 2003, Pages 47-52

  Ahmed, Aqeel ^a   Crawford, Terry ^a   Gould, Stephanie ^a   Ha, Y S ^a   Hollrah, Monica ^a   Noor E Ain, Farhana ^a   Dickman, Martin B ^a   Dussault, Patrick H ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

Asymmetric synthesis; Colletotrichum trifolii; Cutin monomers; DHPA; Dihydroxyhexadecanoic acid; Lycopersicon esculentum; Solonaceae; Tomato

Indexed keywords

10,16 DIHYDROXYHEXADECANOIC ACID; DECANOIC ACID DERIVATIVE; MONOMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLLETOTRICHUM; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; TOMATO;

BLOTTING, NORTHERN; CARBOXYLIC ESTER HYDROLASES; COLLETOTRICHUM; ENZYME ACTIVATION; GENE EXPRESSION REGULATION, FUNGAL; LYCOPERSICON ESCULENTUM; MEMBRANE LIPIDS; PALMITIC ACIDS; PROTEIN KINASES; RNA, FUNGAL; STEREOISOMERISM; TRANSCRIPTION, GENETIC;

COLLETOTRICHUM; COLLETOTRICHUM TRIFOLII; LYCOPERSICON; LYCOPERSICON ESCULENTUM;

EID: 0037403606     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(03)00003-7     Document Type: Article

References (16)

1. Blee, E., Schuber, F., 1993. Biosynthesis of cutin monomers: involvement of a lipoxygenase/peroxygenase pathway. Plant J. 4, 113-123. (Note: this work describes stereochemical analysis of trihydroxystearates).
2. Cho, S.C., Dussault, P.H., Lisec, A.D., Jensen, E.C., Nickerson, K.W., 1999. Metathesis-based synthesis of jasmonate and homojasmonate lactones, candidates for extracellular quorum sensing molecules in Candida albicans. J. Chem. Soc., Perkin Trans. 1, 193-196.
3. Dale, J.A., Mosher, H.S., 1973. Nuclear magnetic resonance enantiomer reagents, configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 95, 512-519.
4. Dickman, M.B., 2000. Colletotrichum. In: Kronstad, J.W. (Ed.), Fungal Pathology. Kluwer Academic, Dordrecht, pp. 127-148.
5. Dickman M.B., Ha Y.S., Yang Z., Adams B., Huang C., A protein kinase from Colletotrichum trifolii is induced by plant cutin and is Required for appressorium formation. Mol. Plant-Microbe Inter. (in press).
6. Espelie, K.E., Kolattukudy, P.E., 1978. The optical rotation of a major component of plant cutin. Lipids 13, 832-833.
7. Frantz, D.E., Fässler, R., Carreira, E.M., 2000. Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes. J. Am. Chem. Soc. 122, 1806. (Note: We were unsuccessful in applying this reported methodology to the synthesis of intermediate 2).
8. Gérard, H.C., Osman, S.F., Fett, W.F., Moreau, R.A., 1992. Separation, identification, and quantification of monomers from cutin polymers by high performance liquid chromatography and evaporative light scattering detection. Phytochemical Analysis 3, 139-144.
9. Kolattukudy, P.E., 2001. Polyester in higher plants. In: Babel, W., Steinbüchel, A. (Eds.), Advances in Biochemical Engineering/Biotechnology, Vol 71. Springer, Berlin, pp. 1-49.
10. Kolattukudy, P.E., Li, D., Hwang, C.-S., Flaishman, M.A., 1995a. Host signals in fungal gene expression involved in penetration into the host. Can. J. Biol. 73, S1160-1168.
11. Kolattukudy, P.E., Rogers, L.M., Li, D., Hwang, C.-S., Flaishman, M.A., 1995b. Surface signaling in pathogenesis. Proc. Nat. Acad. Sci., USA 92, 4080-4087.
12. Podilla, G., Dickman, M.B., Kolattukudy, P.E., 1988. Transcriptional activation of a cutinase gene in isolated fungal nuclei by plant cutin monomers. Science 242, 922-925.
13. Schreiber, S.L., Claus, R.E., Reagan, J., 1982. Ozonolytic cleavage of cycloalkenes to terminally differentiated products. Tetrahedron Lett. 23, 3867-3870.
14. Singh V. K., 1992. Practical and useful methods for the enantioselective reduction of unsymmetrical ketones. Synthesis: 607-617.
15. Sonnet, P.E., Osman, S.F., Gérard, H.C., Dudley, R.L., 1994. Synthesis and configurational analysis of 9,18- and 10,18-dihydroxystearic acid methyl esters. Chem. Phys. Lipids 69, 121-128.
16. Tulloch, A.P., 1980. Cutin acids: synthesis and mass spectrometry of methyl 16-hydroxy-7-oxo-, 16-hydroxy-8-oxo-, 16-hydroxy-9-oxo-, 16-hydroxy-10-oxo- and 7,16-, 8,16-, 9,16- and 10,16-dihydroxy- hexadecanoates. Lipids 15, 881-888.