Nobuhiro Kanomata
Waseda University
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Featured researches published by Nobuhiro Kanomata.
Proceedings of the National Academy of Sciences of the United States of America | 2015
Tomohiko Matsuo; Tatsuya Hattori; Akari Asaba; Naokazu Inoue; Nobuhiro Kanomata; Takefumi Kikusui; Reiko Kobayakawa; Ko Kobayakawa
Significance It is now widely accepted that the range of pheromones that control social behaviors are processed by both the vomeronasal system (VNS) and the main olfactory system (MOS). However, the functional contributions of each subsystem in social behavior remain unclear. Here, we showed that mice with loss-of-function confined to the dorsal MOS maintained innate odor recognition and VNS activity, but failed to demonstrate multiple male and female social behaviors. Functional dissociation of the MOS and VNS enabled the identification of an MOS-mediated processing of semiochemical information, independent of the VNS. Most mammals have two major olfactory subsystems: the main olfactory system (MOS) and vomeronasal system (VNS). It is now widely accepted that the range of pheromones that control social behaviors are processed by both the VNS and the MOS. However, the functional contributions of each subsystem in social behavior remain unclear. To genetically dissociate the MOS and VNS functions, we established two conditional knockout mouse lines that led to either loss-of-function in the entire MOS or in the dorsal MOS. Mice with whole-MOS loss-of-function displayed severe defects in active sniffing and poor survival through the neonatal period. In contrast, when loss-of-function was confined to the dorsal MOB, sniffing behavior, pheromone recognition, and VNS activity were maintained. However, defects in a wide spectrum of social behaviors were observed: attraction to female urine and the accompanying ultrasonic vocalizations, chemoinvestigatory preference, aggression, maternal behaviors, and risk-assessment behaviors in response to an alarm pheromone. Functional dissociation of pheromone detection and pheromonal induction of behaviors showed the anterior olfactory nucleus (AON)-regulated social behaviors downstream from the MOS. Lesion analysis and neural activation mapping showed pheromonal activation in multiple amygdaloid and hypothalamic nuclei, important regions for the expression of social behavior, was dependent on MOS and AON functions. Identification of the MOS-AON–mediated pheromone pathway may provide insights into pheromone signaling in animals that do not possess a functional VNS, including humans.
Tetrahedron Letters | 2001
Nobuhiro Kanomata; Yoshiharu Ochiai
Abstract Stereocontrol of cyclophane-type planar chirality was achieved by spontaneous dynamic resolution via crystallization-induced asymmetric transformation. Simply heating a 1/1 mixture of the solid and the liquid diastereoisomers of bridged nicotinamides ( S ,3′ S )- 1a – f and ( R ,3′ S )- 2a – f accelerated their rope-skipping isomerization with precipitation of the solid ( S ,3′ S )- 1a – f , completing the disequilibriation to ( S ,3′ S )- 1a – f with up to 99% de.
Journal of the American Chemical Society | 2011
Ryo Maeda; Takehiko Wada; Tadashi Mori; Shigeyuki Kono; Nobuhiro Kanomata; Yoshihisa Inoue
Photochemical planar-to-planar chirality transfer was effected by using (R)-[10]paracyclophane-12-carboxylates as a planar-chiral sensitizer and (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene as prochiral substrates to give a planar-chiral (E)- and (E,Z)-isomer in up to 44% and 87% enantiomeric excess, respectively, the latter of which being the highest ever reported for a sensitized photochirogenic reaction.
Tetrahedron Letters | 2003
Nobuhiro Kanomata; Satoshi Maruyama; Katsuhito Tomono; Shinnosuke Anada
A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide–carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.
Tetrahedron Letters | 1988
Nobuhiro Kanomata; Makoto Nitta
Abstract The facile synthesis of [n](2,4)pyridinophane ring system (n = 9–6) was accomplished by the reaction of N-(1-phenylvinyl)iminophosphorane with cyclic α, β-unsaturated ketones. The chain flipping was studied by 1H NMR spectra at various temperatures.
Tetrahedron Letters | 1992
Makoto Nitta; Hiroyuki Kawaji; Nobuhiro Kanomata
The title compound was synthesized by thermal reaction of 3-phosphoranylidene-amino-1,6-methano[10]annulene with 2-chlorotropone in a single step. The examination of 1H NMR spectrum revealed that there is little contribution of peripheral 18-π electron conjugation, but it is rather composed of 1-azaazulene and methano[10]annulene moieties.
Angewandte Chemie | 1998
Nobuhiro Kanomata; Masayuki Suzuki; Mamiko Yoshida; Tadashi Nakata
Just like in biological systems, the GAPDH-catalyzed oxidation of aldehyde to carboxylate proceeds in conjunction with 1,4-selective reduction of NAD+ to NADH model compounds [Eq. (1)]. The combination of GAPDH- and LDH-type transfer reactions is also described here as a system mimic for the NAD+ /NADH redox cycle in anaerobic glycolysis. GAPDH=D-glyceraldehyde-3-phosphate dehydrogenase, LDH=L-lactate dehydrogenase.
Tetrahedron Letters | 2003
Nobuhiro Kanomata
Stereocontrol of cyclophane-type planar chirality was investigated via adsorption-induced asymmetric transformation (AIAT) on a series of inorganic porous adsorbents. The rope-skipping equilibria between bridged nicotinamides (S,3′S)-1 and (R,3′S)-2 shifted preferentially to (R,3′S)-2 to accumulate (R)-configuration of planar chirality with up to 61% de (ca. 4/1 ratio) on alumina. The results are in good contrast to accumulation of the corresponding (S)-configuration via conventional crystallization-induced asymmetric transformation (CIAT) to the solid (S,3′S)-1a–d.
Organic Letters | 2011
Yuko Izuchi; Hiroyuki Koshino; Yayoi Hongo; Nobuhiro Kanomata; Shunya Takahashi
Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.
Journal of The Chemical Society-perkin Transactions 1 | 1990
Nobuhiro Kanomata; Makoto Nitta
A short new synthesis of the [n](2,4)pyridinophane ring system (n= 9–6) consists of allowing N-vinyl- and N-(1-phenylvinyl)iminophosphoranes to react with cyclic α,β-unsaturated ketones. Structural studies of the compounds prepared were based on spectroscopic measurements and MNDO calculations. The 1H and 13C NMR spectra at various temperatures showed dynamic behaviour for the oligomethylene chains of [7]- and [6]-(2,4)pyridinophane derivatives (8c,d). The energy barriers ΔGc‡ of the bridge flipping are 12–13 kcal mol–1(Tc, 20 °C) for (8c) and 21–22 kcal mol–1 kcal mol–1(Tc, 150° C) for (8d). The lower-energy process of the oligomethylene chain in (8d) is the pseudorotation with Ea= 10.3 ± 0.2 kcal mol–1, ΔH‡= 9.8 ± 0.2 kcal mol–1, and ΔS‡=–4.8 cal mol–1 deg–1. Two stable conformations of the hexamethylene bridge of (8d) were unambiguously determined by low-temperature NMR. The strain of the [n](2,4)pyridinophane ring system was found to increase as the chain length becomes shorter. Remarkable deformation of the pyridine rings of (8c,d) was suggested by the geometrical optimization by MNDO calculation and the red shift of the UV spectrum.