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Kobe Pharmaceutical University, Organic Chemistry for Life Science

ƐPUBLICATION

2017

Versatile Amine-Promoted Mild Methanolysis of 3,5-Dinitrobenzoates and Its Application to the Synthesis of Colorado Potato Beetle Pheromone
Yamano, Y.; Sasaki, H.; Wada, A.
Chem. Pharm. Bull.
2017, 65(10), 940-944.

3-Methylene-4-amido-1,2-diazetidine as a Formal 1,4-Dipole Precursor: Lewis Acid-Catalyzed Nucleophilic Addition with Silylated Nucleophiles
Okitsu, T.; Kobayashi, K.; Kan, R.; Yoshida, Y.; Matsu, Y.; Wada, A.
Org. Lett.
2017, 19(17), 4592-4595.

Visual adaptation in Lake Victoria cichlid fishes: depth-related variation of color and scotopic opsins in species from sand/mud bottoms
Terai, Y.; Miyagi, R.; Aibara, M.; Mizoiri, S.; Imai, H.; Okitsu, T.; Wada, A.; Takahashi-Kariyazono, S.; Sato, A.; Tichy, H.; Mrosso, H. D. J.; Mzighani, S. I.; Okada, N.
BMC Evol. Biol.
2017, 17:200.

Adaptation of cone pigments found in green rods for scotopic vision through a single amino acid mutation
Kojima, K.; Matsutani, Y.; Yamashita, T.; Yanagawa, M.; Imamoto, Y.; Yamano, Y.; Wada, A.; Hisatomi, O.; Nishikawa, K.; Sakurai, K.; Shichida, Y.
Proc. Natl. Acad. Sci. U. S. A.
2017, 114(21), 5437-5442.

Alternative Formation of Red-Shifted Channelrhodopsins: Noncovalent Incorporation with Retinal-Based Enamine-Type Schiff Bases and Mutated Channelopsin
Okitsu, T.; Matsuyama, T.; Yamashita, T.; Ishizuka, T.; Yawo, H.; Imamoto, Y.; Shichida, Y.; Wada, A.
Chem. Pharm. Bull.
2017, 65(4), 356-358.

Total synthesis of lycopene-5,6-diol and and -carotene-5',6'-diol stereoisomers and their HPLC separation
Yamano, Y.; Nishiyama, Y.; Aoki, A.; Wada, A.
Tetrahedron
2017,73(15), 2043-2052.

Synthesis of Novel Synthetic Vitamin K Analogues Prepared by Introduction of a Heteroatom and a Phenyl Group that Induce Highly Selective Neuronal Differentiation of Neuronal Progenitor Cells
Kimura, K.; Hirota, Y.; Kuwahara, S.; Takeuchi, A.; Tode, C.; Wada, A.; Osakabe, N.; Suhara, Y..
J. Med. Chem.
2017,60(6), 2591-2596.

Solid-State Nuclear Magnetic Resonance Structural Study of the Retinal-Binding Pocket in Sodium Ion Pump Rhodopsin
Shigeta, A.; Ito, S.; Inoue, K.; Okitsu, T.; Wada, A.; Kandori, H.; Kawamura, I.
Biochemistry
2017, 56(4), 543-550.

2016

Modulation of thermal noise and spectral sensitivity in Lake Baikal cottoid fish rhodopsins
Luk, H. L.; Bhattacharyya, N.; Montisci, F.; Morrow, J. M.; Melaccio, F.; Wada, A.; Sheves, M.; Fanelli, F.; Chang, B. S. W.; Olivucci, M.
Sci. Rep.
2016, 6, 38425.

Convergent Synthesis of Dronedarone: An Antiarrhythmic Agent
Okitsu, T.; Ogasahara, M.; Wada, A.
Chem. Pharm. Bull.
2016, 64(8), 1149-1153.

2015

Origin of the low thermal isomerization rate of rhodopsin chromophore
Yanagawa, M.; Kojima, K.; Yamashita, T.; Iwamoto, Y.; Matsuyama, T.; Nakanishi, K.; Yanamo, Y.; Wada, A.; Sako, Y.; Shichida, Y.
Sci. Rep.
2015, 5, 11081.

Characterization of photo-intermediates in the photo-reaction pathways of bacteriorhodopsin Y185F mutant using in situ photo-irradiation solid-state NMR spectroscopy
Oshima, K.; Shigeta, A.; Makino, Y.; Kawamura, I.; Okitsu, T.; Wada, A.; Tuzi, S.; Iwasa, T.; Naito, A.
Photochem. Photobiol. Sci.
2015, 14(9), 1694-1702.

Identical Hydrogen-Bonding Strength of the Retinal Schiff Base between Primate Green- and Red-Sensitive Pigments: New Insight into Color Tuning Mechanism
Katayama, K.; Okitsu, T.; Imai, H.; Wada, A.; Kandori, H.
J. Phys. Chem. Lett.
2015, 6(7), 1130-1133.

Stereocontrolled First Total Synthesis of Salmoxanthin and Deepoxysalmoxanthin
Yamano, Y.; Eno, K.; Hikita, Y.; Kurimoto, H.; Wada, A.
Curr. Org. Synth. 2015, 12(2), 180-188.

Total Synthesis of gobiusxanthin stereoisomers and their application to determination of absolute configurations of epigobiusxanthin
Yamano, Y.; Ematsu, K.; Kuromoto, H.; Maoka, T.; Wada, A.
Mar. Drugs
2015, 13(1), 159-172.

Oxidative Metabolites of Lycopene and -Carotene in Gac (Momordica cochinchinensis)
Maoka, T.; Yamano, Y.; Wada, A.; Etho, T.; Terada, Y.; Tokuda, H.; Nishino, H.
J. Agric. Food Chem. 2015, 63(5), 1622-1630.


2014

Iodocyclization of ethoxyethyl ethers to ynamides: An immediate construction to benzo[b]furans
Okitsu, T.; Nakata, K.; Nishigaki, K.; Michioka, N.; Karatani, M.; Wada, A.
J. Org. Chem.
2014, 79(12), 5914-5920.

Color-discriminating retinal configurations of sensory rhodopsin I by photo-irradiation solid-state NMR spectroscopy
Yomoda, H.; Makino, Y.; Tomonaga, Y.; Hidaka, T.; Kawamura, I.; Okitsu, T.; Wada, A.; Sudo, Y.; Naito, A.
Angew. Chem. Int. Ed. 2014, 53(27), 6960-6964.

Synthesis of (3S,3S')- and meso-stereoisomers of alloxanthin and determination of absolute configuration of alloxanthin isolated from aquatic animals
Yamano, Y.; Maoka, T.; Wada, A.
Mar. Drugs
2014, 12(5), 2623-2632.

Single-molecule observation of the ligand-induced polulation shift of rhodopsin, a G-protein-coupled receptor
Maeda, R.; Hiroshima, M.; Yamashita, T.; Wada, A.; Nishimura, S.; Sako, Y. Shichida, Y.; Imamoto, Y.
Biophys. J. 2014, 106(4), 915-924.


Inhibition of lysine-specific demethylase 1 by the acyclic diterpenoid geranylgeranoic acid and its derivatives
Sakane, C.; Okitsu, T.; Wada, A.; Sagami, H.; Shidoji, Y.
Biochem. Biophys. Res. Commun. 2014, 444(1), 24-29.


2013

Substrate specificity and subcellular localization of the aldehyde-alcohol redox-coupling reaction in carp cones
Sato, S.; Fukagawa, T.; Tachibanaki, S.; Yamano, Y.; Wada, A.; Kawamura, S.
J. Biol. Chem. 2013, 288(51), 36589-36597.

Menadione (vitamin K3) is a catabolic product of oral phylloquinone (vitamin K1) in the intestine and a circulating precursor of tissue menaquinone-4 (vitamin K2) in rats
Hirota, Y.; Tsugawa, N.; Nakagawa, K.; Suhara, Y.; Tanaka, K.; Uchino, Y.; Takeuchi, A.; Sawada, N.; Kamao, M.; Wada, A.; Okitsu, T.; Okano, T.
J. Biol. Chem. 2013, 288(46), 33071-33080.

Stereocontrolled first total synthesis of Amarouciaxanthin A and B
Yamano, Y.; Chary, M. V.; Wada, A.
Org. Lett.
2013, 15(20), 5310-5313.

Solid-state NMR spectroscopy structure determination of a lipid-embedded heptahelical membrane protein
Wang, S; Munro, R. A.; Shi, L.; Kawamura, I.; Okitsu, T.; Wada, A.; Kim, S.-Y.; Jung, K.-H.; Brown, L. S.; Ladizhansky, V.
Nature Methods
2013, 10(10), 1007-1012.

Solid-state NMR 13C and 15N resonance assignments of a seven-transmembrane helical protein Anabaena Sensory Rhodopsin
Wang, S; Shi, L.; Okitsu, T.; Wada, A.; Brown, L. S.; Ladizhansky, V.
Biomol. NMR Assign. 2013, 7(2), 253-256.

Large spectral change due to amide modes of a -sheet upon the formation of an early photointermediate of middle rhodopsin
Furutani, Y.; Okitsu, T.; Reissig, L.; Mizuno, M.; Homma, M.; Wada, A.; Mizutani, Y.; Sudo, Y.
J. Phys. Chem.
B 2013, 117(13), 3449-3458.

Substituent effect of bis(pyridines)iodonium complexes as iodinating reagents: Control of the iodocyclization/oxidation process
Okitsu, T.; Yumitate, S.; Sato, K.; In, Y.; Wada, A.
Chem. Eur. J.
2013, 19(16), 4992-4996.

2012

Correlation between nuptial colors and visual sensitivities tuned by opsins leads to species richness in sympatric Lake Victoria cichild fishes
Miyagi, R.; Terai, Y.; Aibara, M.; Sugawara, T.; Imai, H.; Tachida, H.; Mzighani, S. I.; Okitsu, T.; Wada, A.; Okada, N.
Mol. Biol. Evol.
2012, 29(11), 3281-3296.

Stereoselective total synthesis of the acetylenic carotenoids alloxanthin and triophaxanthin
Yamano, Y.; Chary, M. V.; Wada, A.
Org. Biomol. Chem.
2012, 10(20), 4103-4108.

Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase
Yamano, Y.; Tsuboi, K.; Hozaki, Y.; Takahashi, K.; Jin, X.-H.; Ueda, N.; Wada, A.
Bioorg. Med. Chem.
2012, 20(11), 3658-3665.


Structure-activity relationship of novel menaquinone-4 analogues: Modification of the side chain affects their biological activities
Suhara, Y.; Hanada, N.; Okitsu, T.; Sakaki, M.; Watanabe, M.; Nakagawa, K.; Wada, A.; Takeda, K.; Takahashi, K.; Tokiwa, H.; Okano, T.
J. Med. Chem.
2012, 75(4),1553-1558.

Tandem migration-carboalkoxylation of o-isocyanopheny acetals leading to benzoxazoles
Okitsu, T.; Nagase, K.; Nishio, N.; Wada, A.
Org. Lett.
2012, 14(3), 708-711.

Reaction of acetals with various carbon nucleophiles under non-acidic conditions: C-C bond formation via a pyridinium-type salt
Fujioka, H.; Yahata, K.; Hamada, T.; Okitsu, T.; Sawama, Y.; Ohnaka, T.; Maegawa, T.; Kita, Y.
Chem. Asian J.
2012, 7(2), 367-373.

2011

UV-sensitive photoreceptor protein OPN5 in Humans and mice
Kojima, D.; Mori, S.; Torii, M.; Wada, A.; Morishita, R.; Fukuda, Y.
PLoS One
2011, 6(10), e26388.

An active photo-receptor intermediate revealed by in-situ photo-irradiated solid-state NMR spectroscopy
Tomonaga, Y.; Hidaka, T.; Kawamura, I.; Nishio, T.; Ohsawa, K.; Okitsu, T.; Wada, A.; Sudo, Y.; Kamo, N.; Ramamoorthy, A.; Naito, A.
Biophys. J.
2011, 101(19), L50-52.

Novel iodocyclization method based on the controlling of oxidative aromatization
Okitsu, T.
Yakugaku Zasshi.
2011, 131(9), 1323-1327.

Synthesis of new vitamin K analogues as steroid and xenobiotic receptor (SXR) agonists: Insights into the biological role of the side chain part of vitamin K
Suhara, Y.; Watanabe, M.; Motoyoshi, S.; Nakagawa, K.; Wada, A.; Takeda, K. Takahashi, K.; Tokiwa, H.; Okano, T.
J. Med. Chem.
2011, 54(13), 4918-4922.

Synthesis of novel vitamin K2 analogues with modification at the -terminal position and their biological evaluation as potent steroid and xenobiotic receptor (SXR) agonists
Suhara, Y.; Watanabe, M.; Nakagawa, K.; Wada, A.; Ito, Y.; Takeda, K.; Takahashi, K.; Okano, T.
J. Med. Chem.
2011, 54(12), 4269-4273.

Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2,5-dihydroisoxazoles and isoxazoles
Okitsu, T.; Sato, K.; Potewar, T. M.; Wada, A.
J. Org. Chem.
2011, 76(9), 3438-3449.

Replacement of the hydrophobic part of 9-cis-retinoic acid with cyclic terpenoid moiety results in RXR-selective agonistic activity
Okitsu, T.; Sato, K.; Iwatsuka, K.; Sawada, N.; Nakagawa, K.; Okano, T.; Yamada, S.; Kakuta, H.; Wada, A.
Bioorg. Med. Chem.
2011, 19(9), 2939-2949.

2010

Carotenoid and related polyenes, part 12 First total synthesis and absolute configuration of 3'-deoxycapsanthin and 3,4-dehydroxy-3'-deoxycapsanthin
Yamano, Y.; Chary, M. V.; Wada, A.
Chem. Pharm. Bull.
2010, 58(10), 1362-1365.

Reagent-controlled oxidative aromatization in iodocyclization: Switchable access to dihydropyrazoles and pyrazoles
Okitsu, T.; Sato, K.; Wada, A.
Org. Lett.
2010, 12(15), 3506-3509.

Efficinet synthesis and biological evaluation of demethyl geranylgeranioc acid derivatives
Wada, A.; Wang, F.; Suhara, Y.; Yamana, Y.; Okitsu, T.; Nakagawa, K.; Okano, T.
Bioorg. Med. Chem.
2010, 18(16), 5795-5806.

Structure-activity relationships in the conversion of vitamin K analogs into menquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines
Suhara, Y.; Wada, A.; Tachibana, Y.; Watanabe, M.; Nakagawa, K.; Okano, T.
Bioorg. Med. Chem.
2010, 18(9), 3116-3124.


Synthesis and biological evaluation of 9Z-retinoic acid analogs having 2-substituted benzo[b]furan
Okitsu, T.; Nakazawa, D.; Nakagawa, K.; Okano, T.; Wada, A.
Chem. Pharm. Bull.
2010, 58(3), 418-422.

ipso-Iodocyclization of ethoxyethyl ethers to alkynes at the ortho-position: An efficient synthesis of functionalized spiro compounds
Okitsu, T.; Nakazawa, D.; Kobayashi, A.; Mizohata, M.; In, Y.; Ishida, T.; Wada, A.
Synlett
2010, (2), 203-206.

2009

Carotenoid synthesis: Retrospect and recent progress
Ito, M.; Yamano, Y.; Tode, C.; Wada, A.
Arch. Biochem. Biophys.
2009, 483(2), 224-228.


Organic chemistry using weakly electrophilic salts: The reaction with nitrogen nucleophiles
Fujioka, H.; Kubo, O.; Senami, K.; Okamoto, K.; Okitsu, T.; Kita, Y
Heterocycles
2009, 79(1), 1113-1120.

Mild and efficient deprotection of acetal-type protecting groups of hydroxyl functions by triethylsilyl triflate-2,4,6-collidine combination
Fujioka, H.; Kubo, O.; Okamoto, K.; Senami, K.; Okitsu, T.; Ohnaka, T.; Sawama, Y.; Kita, Y.

Heterocycles 2009, 77(2), 1089-1103.

Elucidation of the mechanism producing menaquinone-4 in osteoblasic cells
Suhara, Y.; Wada, A.; Okano, T.
Bioorg. Med. Chem. Lett. 2009, 19(4), 1054-1057.

2008

Caesium fluoride-promoted Stille coupling reaction: An efficient synthesis of 9Z-retinoic acid and its analogues using a practical building block
Okitsu, T.; Iwatsuka, K.; Wada, A.
Chem. Commun. 2008, (47), 6330-6332.

Iodocyclization of ethoxyethyl ethers to alkynes: A broadly applicable synthesis of 3-iodobenzo[b]furans
Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A.
Org. Lett. 2008, 10(21), 4967-4970.

Total synthesis of cucurbitaxanthin A, cycloviolaxanthin and capsanthin 3,6-epoxide by applying a regioselective ring opening of tetrasubstituted epoxides
Yamano, Y.; Ito, M.; Wada, A.
Org. Biomol. Chem. 2008, 6(18), 3421-3427.

Preparation and biological evaluation of 5-substituted retinoic acids
Wada, A.; Matsuura, N.; Mizuguchi, Y.; Nakagawa, K.; Ito, M.; Okano, T.
Bioorg. Med. Chem. 2008, 16(18), 8471-8481.

Interacting targets of the farnesyl of transducin -subunit
Katadae, M.; Hagiwara, K.; Wada, A.; Ito, M.; Umeda, M.; Casey, P. J.; Fukada, Y.
Biochemistry 2008, 47(23), 8424-8433.

Steric constraint in the primary photoproduct of sensory rhodopsin II is a prerequisite for light-signal transfer to HtrII
Ito, M.; Sudo, Y.; Furutani, Y.; Okitsu, T.; Wada, A.; Homma, M.; Spudich, J. L.; Kandori, H.
Biochemistry 2008, 47(23), 6208-6215.

Excitation followed by stimulated-emission from diabatic levels in all-trans- and 15-cis-- carotenes: Effects of molecular symmetry and solvent polarity
Bialek-Bylka, G. E.; Kakitani, Y.; Li, C.; Koyama, Y.; Kuki, M.; Yamano, Y.; Nagae, H
Chem. Phys. Lett. 2008, 454(4-6), 367-373.

Stabilization of liposomal membranes by carotenoids: Zeaxanthin, zeaxanthin glucoside and thermozeaxanthin
Hara, M.; Yamano, Y.; Sakai, Y.; Kodama, E.; Hoshino, T.; Ito, M.; Miyake, J.
Materials Science & Engineering, C 2008, 28(2), 274-279.

A convenient and stereoselective synthesis of 11Z-3,4-didehydroretinal by Horner-Emmons reaction using diphenyl phosphonate
Wada, A.; Wang, F.; Ito, M.
Chem. Pharm. Bull. 2008, 56(1), 112-114.

2007

Concise asymmetric total synthesis of scyphostatin, a potent inhibitor of neutral sphingomyelinase
Fujioka, H.; Sawama, Y.; Kotoku, N.; Ohnaka, T.; Okitsu, T.; Murata, N.; Kubo, O.; Li, R.; Kita, Y.
Chem. Eur. J. 2007, 13(36), 10225-10238.

Organic chemistry using weakly electrophilic salts: Efficient formation of O,O-mixed, O,S- and N,O-acetals
Fujioka, H.; Okitsu, T.; Ohnaka, T.; Li, R.; Kubo, O.; Okamoto, K.; Sawama, Y.; Kita, Y.
J. Org. Chem. 2007, 72(21), 7898-7902.

Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides
Yamano, Y.; Ito, M.
Org. Biomol. Chem. 2007, 5(19), 3207-3212.

Two isoforms of chicken melanopsins show blue light sensitivity
Torii, M.; Kojima, D.; Okano, T.; Nakamura, A.; Terakita, A.; Shichida, Y.; Wada, A.; Fukuda, Y.
FEBS Lett. 2007, 581(27), 5327-5331.

Synthesis of -hydroxybutenolides applying crossed aldol condensation in the presence of a bulky Lewis acid and their anti-tumor activity
Yamano, Y.; Fujita, Y.; Mizuguchi, Y.; Nakagawa, K.; Okano T.; Ito, M.; Wada, A.
Chem. Pharm. Bull. 2007, 55(9), 1365-1370.

Alkyl- and arylation of oxacyclic ethers with triethylsilyl triflate-2,4,6-collidine-Gilman reagent combination reaction: Remarkable discrimination of two ether oxygens
Fujioka, H.; Ohnaka, T.; Okitsu, T.; Kubo, O.; Okamoto, K.; Sawama, Y.; Kita, Y.
Heterocycles 2007, 72(1), 529-540.

Reaction of tetrahydropyranyl ethers with triethylsilyl trifluoromethanesulfonate-2,4,6-collidine combination: Speculation on the intermediate, efficient deprotection, and application to efficient ring-closing metathesis
as a tether
Fujioka, H.; Okitsu, T.; Ohnaka, T.; Sawama, Y.; Kubo, O.; Okamoto K.; Kita, Y.
Adv. Synth. Catal. 2007, 349(4-5), 636-646.

Quantification of fat-soluble vitamins in human breast milk by liquid chromatography-tandem mass spectrometry
Kamao, M.; Tsugawa, N.; Suhara, Y.; Wada, A.; Mori, T.; Murata, K.; Nishino, R.; Ukita, T.; Uenishi, K.; Tanaka, K.; Okano T.
J. Chromatogr. B 2007, 859(2), 192-200.

Preparation and biological activities of heteroarotinoids
Wada, A.; Mizuguchi, Y.; Miyake, H.; Niihara, M.; Ito, M.; Nakagawa, K.; Okano, T.
Lett. Drug Des. Disc. 2007, 4(6), 442-445.

2006

Assignment of the hydrogen-out-of-plane and -in-plane vibrations of the retinal chromophore in the K intermediate of pharaonis phoborhodoposin
Furutani, Y.; Sudo, Y.; Wada, A.; Ito, M.; Shimono, K.; Kamo, N; Kandori, H.
Biochemistry 2006, 45(39), 11836-11843.

Highly chemoselective alkylation of acetals using TESOTf-2,4,6-collidine-Gilman reagent combination
Fujioka, H.; Okitsu, T.; Sawama, Y.; Ohnaka, T.; Kita, Y.
Synlett 2006, (18), 3077-3080.

Reaction of the acetals with TESOTf-base combination; Speculation of the intermediates and efficient mixed acetal formation
Fujioka, H.; Okitsu, T.; Sawama, Y.; Murata, N.; Li, R.; Kita, Y.
J. Am. Chem. Soc. 2006, 128(17), 5930-5938.

A novel synthesis of 2-substituted indole derivatives: A palladium catalyzed cross-coupling reaction of enol triflate derived from N-methyl-2-indolone with (alkenyl)tributylstannane and acetylene
Wada, A.; Shinmen, M.; Uenishi, J.; Ito, M.
Lett. Org. Chem. 2006, 3(11), 817-819.

Antitumoral activity of 13-demethyl or 13-substituted analogues of all-trans retinoic acid and 9-cis retinoic acid in the human myeloid leukemia cell line HL-60
Mizuguchi, Y.; Wada, A.; Nakagawa, K.; Ito, M.; Okano, T.
Biol. Pharm. Bull. 2006, 29(9),1803-1809.

Preparation and biological activity of retinoic acid analogs containing an aromatic ring.
Wada, A.; Mizuguchi, Y.; Shinmen, M.; Ito, M.; Nakagawa, K.; Okano, T.
Lett. Drug Des. Disc. 2006, 3(2),118-122.

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