Synthesis of 1-O-(indol-3-ylacetyl)-α-D-glucopyranose and its rearrangement into 2-O-(indol-3-ylacetyl)-D-glucopyranose

Partial Purification and Characterization of Indol-3-Ylacetylglucosemyo-Inositol Indol-3-Ylacetyltransferase (Indoleacetic Acid-Inositol Synthase)

“…In aqueous solution, especially at a pH of 7 or above, the IAA moiety migrates to the position farthest from the carbonyl, that is, the 4-0 and 6-0 position. Owing to this facile acyl migration (1 1, 13,19,20,[25][26][27]) the bond energy of the acyl alkyl acetal is not readily determined but the equilibrium of the reaction:…”

“…In aqueous solution, especially at a pH of 7 or above, the IAA moiety migrates to the position farthest from the carbonyl, that is, the 4-0 and 6-0 position. Owing to this facile acyl migration (1 1, 13,19,20,[25][26][27]) the bond energy of the acyl alkyl acetal is not readily determined but the equilibrium of the reaction:is of the order of Keq = 10-' (27) thus placing the free energy of hydrolysis of IAA glucose at about 1400 calories above that ofthe phosphato glucose bond of UDPG and many thousands of calories above that of an ester bond.These observations concerning energetics may explain the thermodynamics of the manner in which liquid endosperm of maize can contain 0.1 mm IAA ester. Once 1-0-IAGlu is synthesized, even with a large positive free energy change, the IAA may be transacylated to an acceptor alcohol such as myoinositol with a large negative free energy change.…”

Enzymic synthesis of 1-O-indol-3-ylacetyl-β-d-glucose and indol-3-ylacetyl-myo-inositol

“…The arabinose or galactose residue of the IAA-myo-inositol glycosides is linked to the 5-0-position of myo-inositol (Ueda et al, 1970;Ueda & Bandurski, 1974). Trace amounts of the 2-0-, 4-0-and 6-0-esters of glucose with IAA-OH are also found (Ehmann, 1974), but the isolation conditions used would have precluded detection of the 1-0-ester, if present (Keglevic, 1971; the present paper).…”

“…Unlabelled ATP, GTP, CTP, UTP, UDP-galactose, UDP-glucose, ADP-glucose, CDP-glucose, GDP-glucose, reduced glutathione and myo-inositol were from Sigma Chemical Co. (St. Louis, MO, U.S.A.). 1-0-IAA-J-D-glucose was a gift from Dr. Dina Keglevic (Keglevic, 1971). (NH4)2SO4 (enzyme grade) was from Mann Research Laboratories (New York, NY, U.S.A.).…”

Synthesis of the β‐D‐glucosyl ester of [carbonyl‐13C]‐indole‐3‐acetic acid

“…Its homogeneity was confirmed by thin-layer chromatography and analytical HPLC. These methods are appropriate to detect products of aCyl migration, 2-0, 4-0, and 6 -0 esters of IAA and glucose, as the most critical contaminants (13,23). Such impurities would also reveal themselves by additional HI-NMR signals in the region characteristic for the anomeric sugar proton H-1 (23) …”