title: Synthesis and Applications of (ONO Pincer)Ruthenium-Complex-Bound Norvalines.
abstract: Two (ONO pincer)ruthenium-complex-bound norvalines, Boc-[Ru(pydc)(terpy)]Nva-OMe (1; Boc=tert-butyloxycarbonyl, terpy=terpyridyl, Nva=norvaline) and Boc-[Ru(pydc)(tBu-terpy)]Nva-OMe (5), were successfully synthesized and their molecular structures and absolute configurations were unequivocally determined by single-crystal X-ray diffraction. The robustness of the pincer Ru complexes and norvaline scaffolds against acidic/basic, oxidizing, and high-temperature conditions enabled us to perform selective transformations of the N-Boc and C-OMe termini into various functional groups, such as alkyl amide, alkyl urea, and polyether groups, without the loss of the Ru center or enantiomeric purity. The resulting dialkylated Ru-bound norvaline, n-C11 H23 CO-l-[Ru(pydc)(terpy)]Nva-NH-n-C11 H23 (l-4) was found to have excellent self-assembly properties in organic solvents, thereby affording the corresponding supramolecular gels. Ru-bound norvaline l-1 exhibited a higher catalytic activity for the oxidation of alcohols by H2 O2 than parent complex [Ru(pydc)(terpy)] (11 a).
authors.affiliation: International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan), Fax: (+81) 774-38-3186. kisozaki@scl.kyoto-u.ac.jp.|Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan. kisozaki@scl.kyoto-u.ac.jp.|JST CREST, Japan. kisozaki@scl.kyoto-u.ac.jp.
authors.forename: Katsuhiro
authors.initials: K
authors.lastname: Isozaki
authors.affiliation: International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan), Fax: (+81) 774-38-3186.|Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Tomoya
authors.initials: T
authors.lastname: Yokoi
authors.affiliation: International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan), Fax: (+81) 774-38-3186.|Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Ryota
authors.initials: R
authors.lastname: Yoshida
authors.affiliation: International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan), Fax: (+81) 774-38-3186.|Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
authors.forename: Kazuki
authors.initials: K
authors.lastname: Ogata
authors.affiliation: Materials Characterization Support Unit, RIKEN Center for Emergent Matter Science (CEMS), Wako, Saitama, 351-0198, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Hashizume
authors.affiliation: JASRI (SPring-8), 1-1 Koto, Sayo, Hyogo, 679-5198, Japan.
authors.forename: Nobuhiro
authors.initials: N
authors.lastname: Yasuda
authors.affiliation: Department of Biomedical Information Faculty of Life and Medical Sciences, Doshisha University, 1-3 Tatara Miyakotani, Kyotanabe, Kyoto, 610-0321, Japan.
authors.forename: Koichiro
authors.initials: K
authors.lastname: Sadakane
authors.affiliation: International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan), Fax: (+81) 774-38-3186. takaya@scl.kyoto-u.ac.jp.|Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan. takaya@scl.kyoto-u.ac.jp.
authors.forename: Hikaru
authors.initials: H
authors.lastname: Takaya
authors.affiliation: International Research Center for Elements Science, Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan), Fax: (+81) 774-38-3186. masaharu@scl.kyoto-u.ac.jp.|Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan. masaharu@scl.kyoto-u.ac.jp.
authors.forename: Masaharu
authors.initials: M
authors.lastname: Nakamura
mesh_terms: D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D055664:Electrochemical Techniques; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry*; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000438:Alcohols; D007659:Ketones; D009942:Organometallic Compounds; D012428:Ruthenium; C005313:norvaline; D014633:Valine
keywords: amino acids; gels; ruthenium; self-assembly; supramolecular chemistry