Pinanediol

In the tested process, the following reagents were used for oxidation carried out with the use of titanium-silicate TS-1 catalysts: α-pinene (98%, Sigma Aldrich, Poznań, Poland), and oxygen (99.99%, Messer, Szczecin, Poland). Moreover, the following compounds were used as standards for chromatographic analyzes: α-pinene oxide (97%, Sigma Aldrich, Poznań, Poland), verbenol (95%, Sigma Aldrich, Poznań, Poland), verbenone (≥93%, Sigma Aldrich, Poznań, Poland), trans-pinocarveol (≥96%, Sigma Aldrich, Poznań, Poland), myrtenal (98%, Sigma Aldrich, Poznań, Poland), myrtenol (95%, Sigma Aldrich, Poznań, Poland), carveol (≥95%, Sigma Aldrich, Poznań, Poland), carvone (98%, Sigma Aldrich, Poznań, Poland), pinanediol (99%, Sigma Aldrich, Poznań, Poland). Campholenic aldehyde was identified by GC-MS method.

N-Boc-pyrrolidine, sec-butyllithium solution (1.4 M in cyclohexane), trimethyl borate, (1S,2S,3R,5S)-(+)-Pinanediol, Boc-Ala-OH, phenylboronic acid and Ethylenediamine-N,N′-diacetic acid (EDDA) were provided by Sigma-Aldrich Chemical Co. (St. Louis, MO, USA); succinimidyl-N-Boc-HYNIC was supplied by Synchem UG & Co (Felsberg-Altenburg, Germany); ^99mTc-pertechnetate was obtained from a ⁹⁹Mo/^99mTc generator (ININ, Mexico); DMEM-F12 culture media was provided by ATCC (Manassas, VA, USA) and the anti-FAP monoclonal antibody by Invitrogen (Waltham, MA, USA); all of the other reagents were of analytical grade and were provided by Merck Millipore Co. (Burlington, MA, USA) and Gibco (Grand Island, NY, USA), as mentioned in each case; the N30cell line was obtained in the Wake Forest School of Medicine, originally donated by Dr. Taylor (Department of Obstetrics and Gynecology, Winston Salem, NC, USA); the Hep-G2 was supplied from ATCC (Atlanta, GA, USA). The human dermal fibroblasts were donated by Dr. Martínez-Gutiérrez from the “Facultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Mexico”.