Indole 3 lactic acid

Indole-3-carboxylic acid (3ICA, 99%), indole-3-acetic acid (3IAA, 98%), indole-3-propionic acid (3IPA, 99%), indole-3-lactic acid (3ILA, 99%), 5-hydroxyindole-3-acetic acid (5HIAA, ≥98%), 2,3,4,5,6-D₅-benzoic acid (internal standard, D₅-BA, ≥99 atom % D, ≥99%), N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA, contains 1% trimethylchlorosilane, 99% BSTFA), N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide (MTBSTFA, >97%), formic acid (≥95%), hexane (≥97.0%), methanol (≥99.9%) were purchased from Sigma-Aldrich (Darmstadt, Germany); sulfuric acid, acetone, diethyl ether were Laboratory Reagent grade and obtained from Khimreactiv (Staryy Oskol, Russia).

¹³C₁₁-Trp and d₇-indole-3-acetic acid (d₇-IAA) were purchased from Cambridge Isotope Laboratories (Tewksbury, MA). Trp, indole-3-lactic acid (ILA), indole-3-ethanol (tryptophol, TOL), indole-3-acetic acid (IAA), indole-3-acetonitrile (IAN), indole-3-acetamide (IAM), tryptamine (TAM) were from Sigma-Aldrich (St. Louis, MO). HPLC grade water and acetonitrile were obtained from Fisher Scientific (Pittsburgh, PA). All other commercially available chemicals were either reagent grade or were of the highest quality.

Methanol (MeOH) of HPLC grade, 2-picolylamine
(2-PA), dipyridyl disulfide (DPDS), triphenylphosphine (TPP), acetic
acid, propionic acid, butyric acid, valeric acid, caproic acid, lactic
acid, succinic acid, isobutyric acid, isovaleric acid, 2-methylbutyric
acid, 3,3-dimethylbutyric acid, 2-methylvaleric acid, 3-methylvaleric
acid, 4-methylbutyric acid, indole-3-acetic acid, indole-3-butyric
acid, indole-3-lactic acid, 2-ethylbutyric acid (2-EtB), d⁴-acetic acid, glucose, galactose, fructose, arabinose, fucose, rhamnose,
glucuronic acid, galacturonic acid, Nacetylglucosamine, N-acetylgalactosamine, mannose, allose, ribose, 3-methyl-1-phenyl-2-
pyrazoline-5-one (PMP), trifluoroacetic acid (TFA), and ammonium acetate
were purchased from Sigma-Aldrich (St. Louis, MO). d²-indole-3-propionic
acid was purchased from Toronto Research Chemicals (Toronto, Canada).
Algal starch (U–¹³C, 98%+), ¹³C₆ glucose, and unlabeled algal starch were purchased from Cambridge
Isotope Laboratories (Tewksbury, MA). Isopropanol of LC/MS grade was
purchased from Fisher Scientific (Waltham, MA). Acetonitrile (HPLC-grade)
was purchased from Honeywell (Muskegon, MI).