12 oxo 9 z dodecenoic acid

Safflower oil was purchased from Gefro (Germany) and had a fatty acid composition of 77.2% linoleic acid, 13.3% oleic acid, 2.4% stearic acid, 6.7% palmitic acid, and 0.4% of other fatty acids [11 (link)]. 13S-HPODE, 12-oxo-9(Z)-dodecenoic acid, and 12-oxo-10(E)-dodecenoic acid standards were from Larodan (Sweden). Hexanal, hexanol, and 12-hydroxydodecanoic acid standards, Glycine max LOX-1, and P. fluorescens Amano lipase were obtained from Sigma-Aldrich (USA). linoleic acid was purchased from Thermo Fisher Scientific (USA), and δ-aminolevulinic acid (ALA), Triton X-100, isopropyl β-d-1-thiogalactopyranoside (IPTG), as well as kanamycin sulfate and ampicillin sodium salt were obtained from Carl Roth (Germany). All other solvents and chemicals were supplied by Carl Roth (Germany), Sigma-Aldrich (USA), or Thermo Fisher Scientific (USA). For PCR, Phusion Hot Start DNA polymerase with 5 × Phusion High-fidelity buffer and dNTPs were obtained from Thermo Fisher Scientific (USA). PageRuler™ Prestained Protein ladder, restriction enzymes, and the monoclonal AP-conjugated Anti-His (C-term) antibody (AB_2556555) were purchased from Thermo Fisher Scientific (USA) as well. Alkaline phosphatase was obtained from New England Biolabs GmbH (Germany).

The 12-aminododecanoic acid standard was purchased from Alfa Aesar (Haverhill, MA, USA), while the 12-oxo-9(Z)-dodecenoic acid and 12-oxo-10(E)-dodecenoic acid standards were purchased from Larodan (Solna, Sweden). Pyridoxal-5-phosphate monohydrate (PLP) was obtained from Acros Organics, Thermo Fisher Scientific (Waltham, MA, USA). Hexanal, hexylamine, soybean LOX-1, and L-lactate dehydrogenase (LDH) were supplied from Sigma Aldrich (St. Louis, MO, USA). Linoleic acid was obtained from Thermo Fisher Scientific (Waltham, MA, USA). β-Nicotine amide adenine dinucleotide disodium salt (NADH), isopropyl β-d-1-thiogalactopyranoside (IPTG), l-alanine, imidazole, ampicillin sodium salt, and kanamycin sulfate were purchased from Carl Roth (Karlsruhe, Germany). 13S-Hydroperoxy-9(Z),11(E)-octadecadienoic acid (13S-HPODE) was prepared from Linoleic acid by a peroxidation reaction with LOX-1 from Glycine max as described previously (Gala Marti et al. 2021 (link)). All other chemicals were from Sigma-Aldrich (St. Louis, MO, USA), Thermo Fisher Scientific (Waltham, MA, USA) or Carl Roth (Karlsruhe, Germany).