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

Abstract

An efficient, operationally simple synthetic approach to 1‐O‐([carbonyl‐13C]‐indole‐3′‐ylacetyl)‐β‐D‐glucopyranose is described. The synthesis was carried out by fusing a fully benzylated 1‐O‐glucosylpseudourea intermediate with [carbonyl‐13C]‐indole‐3‐acetic acid, followed by hydrogenolytic removal of the protective groups.

Bifunctional indole‐3‐acetyl transferase catalyses synthesis and hydrolysis of indole‐3‐acetyl‐myo‐inositol in immature endosperm of Zea mays

“…[ 14 C] myo ‐inositol was from Amersham Pharmacía Biotech ABSE 75184 (Uppsala, Sweden). 1‐ O ‐(indole‐3‐ylacetyl)‐ β ‐ d ‐glucose was synthesized by Dr Antoni Leźnicki using the method of Jakas et al (1993), IA‐ myo ‐inositol was chemically synthesized according to the method of Nowacki et al (1978).…”

Hydrophobic metabolites of 2,4-dichlorophenoxyacetic acid (2,4-D) in cultured coconut tissue

“…Both tetra-acetylated and tetrabenzoylated derivatives were synthesised but various attempts to remove the blocking groups, for instance by hydrogenolysis as described for indol-3-acetic acid (Jakas et al, 1993), also resulted in the hydrolysis of the glucose-2,4-D ester bond. In the end, a different approach was adopted in which the possible glucose ester metabolite was acetylated, and compared with a synthetic tetra-acetyl-glucose ester of 2,4-D.…”

A specific enzyme hydrolyzing 6-O(4-O)-indole-3-ylacetyl-β-d-glucose in immature kernels of Zea mays

“…1-O-IAGlc was synthesized by Dr Antoni Leźnicki using the method of Jakas et al (1993). IAA-myo-inositol was synthesized by the method of Nowacki et al (1978).…”