The use of abscisic acid analogues to analyse the substrate selectivity of UGT71B6, a UDP-glycosyltransferase of Arabidopsis thaliana

FEBS Letters

Volumn 579, Issue 20, 2005, Pages 4454-4458

  Priest, David M ^a   Jackson, Rosamond G ^a   Ashford, David A ^a   Abrams, Suzanne R ^b   Bowles, Dianna J ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Abscisic acid; Analogues; Arabidopsis thaliana; Enantiomer; Glucose ester; Glycosyltransferase

Indexed keywords

ABSCISIC ACID; GLYCOSYLTRANSFERASE; KETONE; METHYL GROUP; PHYTOHORMONE; URIDINE DIPHOSPHATE;

ARABIDOPSIS; ARTICLE; CHEMICAL BOND; CHIRALITY; CONJUGATION; ENZYME ACTIVITY; ENZYME SUBSTRATE; GLYCOSYLATION; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

ABSCISIC ACID; ARABIDOPSIS; ARABIDOPSIS PROTEINS; GLYCOSYLTRANSFERASES; SUBSTRATE SPECIFICITY;

ARABIDOPSIS THALIANA;

EID: 23644433349     PISSN: 00145793     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.febslet.2005.06.084     Document Type: Article

References (27)

1. D.C. Walton, and Y. Li Abscisic acid biosynthesis and metabolism P.J. Davies Plant Hormones - Physiology, Biochemistry and Molecular Biology 1995 Kluwer Academic Publishers Dordrecht 140 157
2. R.R. Finkelstein, and C.D. Rock Abscisic acid biosynthesis and response C.R. Somerville E.M. Meyerowitz The Arabidopsis Book 2002 American Society of Plant Biologists Rockville, MD 1 48
3. J.D. Bewley Seed germination and dormancy Plant Cell 9 1997 1055 1066
4. A.J. Cutler, and J.E. Krochko Formation and breakdown of ABA Trends Plant Sci. 4 1999 472 478
5. J.A.D. Zeevaart Abscisic acid metabolism and its regulation P.J.J. Hooykaas M.A. Hall K.R. Libbenga Biochemistry and Molecular Biology of Plant Hormones 1999 Elsevier Science Amsterdam 189 207
6. L.I. Zaharia, Y.Z. Gai, K.M. Nelson, S.J. Ambrose, and S.R. Abrams Oxidation of 8′-hydroxy abscisic acid in Black Mexican Sweet maize cell suspension cultures Phytochemistry 65 2004 3199 3209
7. C.R. Hampson, M.J.T. Reaney, G.D. Abrams, S.R. Abrams, and L.V. Gusta Metabolism of (+)-abscisic acid to (+)-7′-hydroxyabscisic acid by Bromegrass cell-cultures Phytochemistry 31 1992 2645 2648
8. R. Zhou, A.J. Cutler, S.J. Ambrose, M.M. Galka, K.M. Nelson, T.M. Squires, M.K. Loewen, A.S. Jadhav, A.R.S. Ross, D.C. Taylor, and S.R. Abrams A new abscisic acid catabolic pathway Plant Physiol. 134 2004 361 369
9. K. Koshimizu, M. Inui, H. Fukui, and T. Mitsui Isolation of (+)-abscisylbeta-d-glucopyranoside from immature fruit of Lupinus luteus Agric. Biol. Chem. 32 1968 789 791
10. E.K. Lim, C.J. Doucet, B. Hou, R. Jackson, S.R. Abrams, and D.J. Bowles Resolution of (+)-abscisic acid using an Arabidopsis glycosyltransferase Tetrahedron: Asymm. 16 2005 143 147
11. L.I. Zaharia, M. Galka, S.J. Ambrose, and S.R. Abrams Preparation of deuterated ABA metabolites for mass spectrometry and feeding studies J. Labelled Compd. Radiopharm. 48 2005 435 445
12. H.J. Mayer, N. Rigassi, U. Schwieter, and B.C.L. Weedon Synthesis of abscisic-acid Helv. Chim. Acta 59 1976 1424 1427
13. M.K. Walker-Simmons, R.J. Anderberg, P.A. Rose, and S.R. Abrams Optically pure abscisic acid analogs - tools for relating germination inhibition and gene expression in wheat embryos Plant Physiol. 99 1992 501 507
14. B. Lei, S.R. Abrams, B. Ewan, and L.V. Gusta Achiral cyclohexadienone analogs of abscisic-acid - synthesis and biological-activity Phytochemistry 37 1994 289 296
15. P.A. Rose, B. Lei, A.C. Shaw, M.K. WalkerSimmons, S. Napper, J.W. Quail, and S.R. Abrams Chiral synthesis of (+)-8′-dimethyl abscisic acid Can. J. Chem. 74 1996 1836 1843
16. M.K. Walker-Simmons, P.A. Rose, A.C. Shaw, and S.R. Abrams The 7′-methyl group of abscisic-acid is critical for biological-activity in wheat embryo germination Plant Physiol. 106 1994 1279 1284
17. P.A. Rose, A.J. Cutler, N.M. Irvine, A.C. Shaw, T.M. Squires, M.K. Loewen, and S.R. Abrams 8′-acetylene ABA: an irreversible inhibitor of ABA 8′-hydroxylase Bioorg. Med. Chem. Lett. 7 1997 2543 2546
18. A.J. Cutler, P.A. Rose, T.M. Squires, M.K. Loewen, A.C. Shaw, J.W. Quail, J.E. Krochko, and S.R. Abrams Inhibitors of abscisic acid 8′-hydroxylase Biochemistry 39 2000 13614 13624
19. E.K. Lim, Y. Li, A. Parr, R. Jackson, D.A. Ashford, and D.J. Bowles Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis J. Biol. Chem. 276 2001 4344 4349
20. E.K. Lim, R.G. Jackson, and D.J. Bowles Identification and characterisation of Arabidopsis glycosyltransferases capable of glucosylating coniferyl aldehyde and sinapyl aldehyde FEBS Lett. 579 2005 2802 2806
21. R.G. Jackson, E.K. Lim, Y. Li, M. Kowalczyk, G. Sandberg, J. Hoggett, D.A. Ashford, and D.J. Bowles Identification and biochemical characterization of an Arabidopsis indole-3-acetic acid glucosyltransferase J. Biol. Chem. 276 2001 4350 4356
22. Z.J. Xu, M. Nakajima, Y. Suzuki, and I. Yamaguchi Cloning and characterization of the abscisic acid-specific glucosyltransferase gene from Adzuki bean seedlings Plant Physiol. 129 2002 1285 1295
23. T. Kushiro, M. Okamoto, K. Nakabayashi, K. Yamagishi, S. Kitamura, T. Asami, N. Hirai, T. Koshiba, Y. Kamiya, and E. Nambara The Arabidopsis cytochrome P450CYP707A encodes ABA 8′-hydroxylases: key enzymes in ABA catabolism EMBO J. 23 2004 1647 1656
24. S. Saito, N. Hirai, C. Matsumoto, H. Ohigashi, D. Ohta, K. Sakata, and M. Mizutani Arabidopsis CYP707As encode (+)-abscisic acid 8′-hydroxylase, a key enzyme in the oxidative catabolism of abscisic acid Plant Physiol. 134 2004 1439 1449
25. R.G. Jackson, M. Kowalczyk, Y. Li, G. Higgins, J. Ross, G. Sandberg, and D.J. Bowles Over-expression of an Arabidopsis gene encoding a glucosyltransferase of indole-3-acetic acid: phenotypic characterisation of transgenic lines Plant J. 32 2002 573 583
26. K. Ueno, Y. Araki, N. Hirai, S. Saito, M. Mizutani, K. Sakata, and Y. Todoroki Differences between the structural requirements for ABA 8′-hydroxylase inhibition and for ABA activity Bioorg. Med. Chem. 13 2005 3359 3370
27. Y. Todoroki, M. Sawada, M. Matsumoto, S. Tsukada, K. Ueno, M. Isaka, M. Owaki, and N. Hirai Metabolism of 5′[alpha],8′-cycloabscisic acid, a highly potent and long-lasting abscisic acid analogue, in radish seedlings Bioorg. Med. Chem. 12 2004 363