Stereoselective enzymatic synthesis of cis-pellitorine, a taste active alkamide naturally occurring in tarragon

European Journal of Organic Chemistry

Volumn , Issue 24, 2004, Pages 5135-5140

  Ley, Jakob P ^a   Hilmer, Jens Michael ^a   Weber, Berthold ^a   Krammer, Gerhard ^a   Gatfield, Ian L ^a   Bertram, Heinz Jürgen ^a  

^a SYMRISE AG   (Germany)

Author keywords

Acylation; Alkamides; Biotransformations; Chemosensates; Diastereoselectivity

Indexed keywords

ENZYME; ESTER; ESTERASE; ETHYL 2,4 DECADIENOATE; NATURAL PRODUCT; PELLITORINE; PROTEINASE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTEMISIA; ARTEMISIA DRACUNCULUS; ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL REACTION; CONCENTRATION RESPONSE; ENZYME ACTIVITY; ENZYME MECHANISM; REACTION ANALYSIS; SENSATION; STEREOCHEMISTRY; SYNTHESIS; TASTE;

EID: 11144294155     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400403     Document Type: Article

References (15)

1. S. K. Adesina, J. Nat. Prod. 1986, 49, 715-716.
2. G. M. Strunz, Stud. Nat. Prod. Chem. 2000, 24 [Bioactive Natural Products (Part E)], 683-738.
3. B. Saadali, D. Boriky, M. Blaghen, M. Vanhaelen, M. Talbi, Phytochemistry 2001, 58, 1083-1086; in contrast to the opinion of the authors, the occurrence of the 2E,4Z-isomer of pellitorine was never described unequivocally in literature.
4. R. S. Ramsewak, A. J. Erickson, M. G. Nair, Phytochemistry 1999, 51, 729-732.
5. H. C. F. Su, R. Horvat, J. Agric. Food Chem. 1981, 29, 115-118.
6. Y. Tsukahara, H. Kinoshita, K. Inomata, H. Kotake, Bull. Chem. Soc., Jpn. 1984, 57, 3013-3014.
7. K. J. Liu, A. Nag, J.-F. Shaw, J. Agric. Food Chem. 2001, 49, 5761-5764.
8. R. Irimescu, K. Kato, Tetrahedron Lett. 2004, 45, 523-525.
9. M. C. de Zoete, A. C. Kock-van Dalen, F. van Rantwijk, R. A. Sheldon, J. Mol. Catal. B: Enzymatic 1996, 2, 141-145.
10. K. Kobata, M. Kobayashi, Y. Tamura, S. Miyoshi, S. Ogawa, T. Watanabe, Biotechnol Lett. 1999, 21, 547-550.
11. L. Crombie, J. Chem. Soc. 1955, 1007-1025.
12. Y. Cai, X.-F Sun, N. Wang, X.-F. Lin, Synthesis 2004, 671-674.
13. B. Bryant, I. Mezine in ACS Symposium Series, Vol. 825, Chemistry of Taste (Eds.: P. Given, D. Paredes), American Chemical Society, Washington D. C. (USA) 2002, pp. 202-212.
14. C. C. Galoph, S. M. Furrer, A. Goeke in ACS Symposium Series, Vol. 867, Challenges in Taste Chemistry and Biology (Eds.: T. Hofmann, C.-H. Ho, W. Pickenhagen), American Chemical Society, Washington D. C. (USA) 2003, pp. 139-152.
15. Anon., Biocatalysts for Industry, Technical Bulletin, Roche Diagnostics 2000/2001, http://indbio.roche.com//Indbio/Ind/CHIRAZYM/Czhfram.htm.