scholarly journals Photostable Abscisic Acid Agonists with a Geometrically Rigid Cyclized Side Chain

2022 ◽  
Author(s):  
Jun Takeuchi ◽  
Saya Mimura ◽  
Toshiyuki Ohnishi ◽  
Yasushi Todoroki
Keyword(s):  
Abscisic Acid ◽  
Side Chain

scholarly journals Abscisic acid analogs with a geometrically rigid conjugated acid side-chain.

1986 ◽  
Vol 50 (4) ◽  
pp. 1097-1100 ◽  
Author(s):  
S. C. CHEN ◽  
J. M. MACTAGGART
Keyword(s):  
Abscisic Acid ◽  
Side Chain

scholarly journals Synthesis of New Abscisic Acid (ABA) Analogs Possessing a Geometrically Rigid Cyclized Side Chain

1992 ◽  
Vol 56 (4) ◽  
pp. 624-629 ◽  
Author(s):  
Bum-Tae Kim ◽  
Tadao Asami ◽  
Kensuke Morita ◽  
Chang-Ho Soh ◽  
Noboru Murofushi ◽  
...  
Keyword(s):  
Abscisic Acid ◽  
Side Chain ◽  
Aba Analogs

Insights into the in Vitro and in Vivo SAR of Abscisic Acid - Exploring Unprecedented Variations of the Side Chain via Cross-Coupling-Mediated Syntheses

2018 ◽  
Vol 2018 (12) ◽  
pp. 1403-1415 ◽  
Author(s):  
Jens Frackenpohl ◽  
Erwin Grill ◽  
Guido Bojack ◽  
Rachel Baltz ◽  
Marco Busch ◽  
...  
Keyword(s):  
Abscisic Acid ◽  
Cross Coupling ◽  
Side Chain

Endogenous biosynthetic precursors of (+)-abscisic acid. VII. The 1′,4′-trans-diol is formed from ABA, it is not a precursor

1998 ◽  
Vol 25 (6) ◽  
pp. 729 ◽  
Author(s):  
B. V. Milborrow ◽  
H.-S. Lee
Keyword(s):  
Abscisic Acid ◽  
Mung Bean ◽  
Cold Trap ◽  
Hydroxyl Group ◽  
Side Chain ◽  
Plant Tissues ◽  
Bean Seedling ◽  
Avocado Fruit ◽  
In Trans ◽  
Reducing Potential

[14C]ABA fed to avocado fruit is known to be converted into the 1′,4′-trans-diol and [14C]1′,4′-trans-diol has been shown to be converted into ABA by several plant tissues. As a ‘cold trap’of trans-diol becomes labelled with 14C when [14C]mevalonate is converted into ABA, the trans-diol has been suggested to be the immediate precursor of ABA. This proposal has now been tested by feeding [5-14C,5-3H2]mevalonolactone to unripe avocado fruit and measuring the 3H :14C ratio in the ABA and in the 1′,4′-trans-diol isolated from the fruit after 16 h. Little labelled diol was present unless a ‘cold trap’ of unlabelled 1,4-trans-diol was added with the mevalonate. One 3H atom, derived from those at C-5 of mevalonate, would be expected at C-4′ of the diol, adjacent to the hydroxyl group, and another at C-5 of the side chain of the diol if the diol were a precursor of ABA (3H:14C ratio of 2:3). However, if the 4′-hydroxyl group had been oxidised to a ketone to form ABA, then the 3H atom at C-4′ of the diol would have been lost and the 3H:14C ratio would be expected to be 1:3. The normalised 3H : 14C ratios of ABA and 1′,4′-trans-diol biosynthesised from [14C,5-3H2]mevalonate were 0.915:3 and 0.844:3 respectively and after oxidation of the diol to ABA with MnO2 the ratio was 0.869:3 i.e. there was no 3H at C-4′ of the diol. These ratios are as expected for the trans-diol if it had been formed by reduction of ABA. This, and the absence of labelled diol in the fruit unless a ‘cold trap’was added, establishes that the 1′,4′-trans-diol is formed from ABA and it is not a precursor. The formation of the diols from newly synthesised labelled ABA in cell-free systems can be attributed to the addition to the homogenate of compounds with strong reducing potential. NADPH2+ (8.4 nmol) added to a mung bean seedling homogenate caused the reduction of (±)-[14C]ABA (0.37 nmol, 22.5 µCi/mol) to trans-diol (1189 dpm) whereas with NADP+ only 338 dpm were present in trans-diol. Glutathione (46 nmol) caused the formation of 1214 dpm while oxidised glutathione produced 638 dpm. Less 1′,4′-cis-diol was formed.

scholarly journals The conformation of abscisic acid by n.m.r. and a revision of the proposed mechanism for cyclization during its biosynthesis

1984 ◽  
Vol 220 (1) ◽  
pp. 325-332 ◽  
Author(s):  
B V Milborrow
Keyword(s):  
Abscisic Acid ◽  
Hydrogen Atom ◽  
Pulse Sequence ◽  
Chair Conformation ◽  
Crystalline Form ◽  
Side Chain ◽  
Hydrogen Atoms ◽  
Methyl Group ◽  
Nuclear Overhauser Enhancement ◽  
Nuclear Overhauser

The n.m.r. spectrum of abscisic acid (ABA) formed from [1,2-13C2]acetate by the fungus Cercospora rosicola shows 13C-13C coupling between C-6′ (41.7 p.p.m.; 36 Hz) and the downfield 6′-methyl group (6′-Me) (24.3 p.p.m, 36 Hz). This 6′-Me, therefore, is derived from C-3′ of mevalonate [Bennett, Norman & Maier (1981) Phytochemistry 20, 2343-2344]. An i.n.e.p.t. (insensitive nuclei enhanced by polarization transfer) pulse sequence demonstrated that the downfield 13C signal is produced by the 6′-Me that gives rise to the upfield 1H 6′-Me signal (23.1 d). The absolute configuration of this, the equatorial 6′-Me group, was determined as 6′-pro-R by decoupling and n.O.e. (nuclear-Overhauser-enhancement) experiments at 300 MHz using ABA, ABA in which the axial 6′-pro-S 5′-hydrogen atom had been exchanged with 2H in NaO2H and the 1′,4′-cis- and 1′,4′-trans-diols formed from these samples. The configuration at C-1′ and at C-6′ are now compatible with a chair-folded intermediate during cyclization, as proposed for beta- and epsilon-rings of carotenoids. ABA in solution exists, as in the crystalline form, with the ring in a pseudo-chair conformation. The side chain is axial and the C-3 Me and the C-5 hydrogen atoms are predominantly cis(Z).

Differential accumulation of methyl jasmonate-induced mRNAs in response to abscisic acid and desiccation in barley (Hordeum vulgare)

1992 ◽  
Vol 86 (1) ◽  
pp. 49-56 ◽  
Author(s):  
Steffen Reinbothe ◽  
Christiane Reinbothe ◽  
Jorg Lehmann ◽  
Benno Parthier
Keyword(s):  
Abscisic Acid ◽  
Hordeum Vulgare ◽  
Methyl Jasmonate

Antitranspirant action of abscisic acid and ten synthetic analogs in black spruce

1990 ◽  
Vol 80 (3) ◽  
pp. 365-370 ◽  
Author(s):  
Terence J. Blake ◽  
Weixing Tan ◽  
Suzanne R. Abrams
Keyword(s):  
Abscisic Acid ◽  
Black Spruce ◽  
Synthetic Analogs

Signalling gates in abscisic acid-mediated control of guard cell ion channels

1997 ◽  
Vol 100 (3) ◽  
pp. 481-490 ◽  
Author(s):  
Michael R. Blatt ◽  
Alexander Grabov
Keyword(s):  
Abscisic Acid ◽  
Ion Channels ◽  
Guard Cell
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