Kenji Mori

Kenji Mori
The University of Tokyo | Todai · Department of Applied Biological Chemistry

PhD

About

1,300
Publications
35,084
Reads
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22,169
Citations
Citations since 2017
7 Research Items
2445 Citations
20172018201920202021202220230100200300400
20172018201920202021202220230100200300400
20172018201920202021202220230100200300400
20172018201920202021202220230100200300400
Additional affiliations
March 2003 - March 2013
RIKEN
Position
  • Senior Researcher

Publications

Publications (1,300)
Article
The structure of the sex pheromone produced by the male sandfly Lutzomyia longipalpis, from the Lapinha Cave (Minas Gerais State) region of Brazil, previously proposed tentatively as the novel homosesquiterpene 9-methylgerma crene-B, is confirmed and the absolute stereochemistry defined as S by comparing physical and biological properties of the sy...
Article
The racemate and the enantiomers of (E)-cis-6,7-epoxy-2-nonenal, the male pheromone of Aromia bungii, were synthesized by olefin cross metathesis between crotonaldehyde and (±)-, (+)- and (-)-cis-3,4-epoxy-7-octene. The epoxide was prepared by the Grignard coupling between allylmagnesium bromide and (±)-, (+)- and (-)-cis-2,3-epoxypentyl triflate....
Article
Full-text available
Various generic transdermal formulations of tulobuterol containing rubber and acrylate base polymers are commercially available in Japan. However, none of the formulations have been compared directly with respect to the skin permeability of tulobuterol and to their follow ability. Tulobuterol Tape Sawai of rubber base and Tulobuterol Tape NP of acr...
Article
Full-text available
A mixture of (E,Z)-isomers of methyl 12-trishomofarnesoate (methyl 3,7,11-trimethyl-2,6,10-pentadecatrienoate), a juvenile hormone mimic, was synthesized in nine steps (32.6% overall yield) by starting from only four commercially available materials: 2-hexanone, vinylmagnesium bromide, methyl acetoacetate and trimethyl phosphonoacetate. The mimic i...
Article
The enantiomers of (anti-1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde, one of which is the female sex pheromone of the pineapple mealybug (Dysmicoccus brevipes), were synthesized. Chirality was introduced by means of lipase-catalyzed asymmetric acetylation of (±)-2,3-dimethyl-2-cyclopenten-l-ol. X-ray analysis of (-)-camphanate ester of (1. S,2...
Article
Four pyrazines were synthesized as sex specific volatiles of female Korean apricot wasp, Eurytoma maslovskii. They are 2,5-dimethyl-3-vinylpyrazine (1), 2,5-dimethyl-3-(2-methylpropyl)pyrazine (2), 2,5-dimethyl-3-(2-methylbutyl)pyrazine (3), and 2,5-dimethyl-3-(3-methylbutylpyrazine (4). They were synthesized in 74–85% yields by Pd- or Fe-catalyzed...
Article
Sex pheromones play a central role in intersexual communication for reproduction in many organisms. Particularly in insects, reproductive isolation that leads to speciation is often achieved by shifts of pheromone chemistries. However, the divergence and evolution of pheromones remain largely unknown. This study reveals a unique evolutionary conseq...
Article
(±)-(anti-1,2-Dimethyl-3-methylenecyclopentyl)acetaldehyde, the racemate of the female-produced sex pheromone of the pineapple mealybug, was synthesized in four different ways. Ireland-Claisen rearrangement or conjugate addition was employed for the construction of the quaternary carbon center, while ring-closing olefin metathesis or cationic cycli...
Article
Seven new methyl-branched hydrocarbons were synthesized, which were the pheromone candidates of the female Korean apricot wasp (_Eurytoma maslovskii_). They are (_Z_)-15-methyl-7-nonacosene (1), (_Z_)-17-methyl-7-hentriacontene (2), 3,7-dimethylheptacosane (3), 8,12-dimethyltriacontane (4), 8,18-dimethyltriacontane (5), 3,7,11-trimethylnonacosane (...
Chapter
Many examples illustrate the application of lipases and esterases as user-friendly biocatalysts in natural products synthesis. Lipases and esterases are used for (i) desymmetrization of prochiral or meso-diols and diacetates, (ii) kinetic resolution of racemic alcohols, and (iii) preparation of enantiopure intermediates from a mixture of stereoisom...
Article
The cocoa weevil Conotrachelus humeropictus is an economically most important pest on cocoa (Theobroma cacao) and cupuaçu (Theobroma grandiflorum) cultures. Knowledge on the pheromone system of this insect is prerequisite for the development of an integrated pest management system. GC/MS-analysis of headspace volatiles revealed the presence of thre...
Article
The enantiomers of citronellal have been converted into the enantiomers of the following beetle pheromones: ethyl 4-methylheptanoate (produced by male Nicrophorus vespilloides), 4-methyloctanoic acid (produced by male Oryctes elegans), and 4-methyl-1-nonanol (produced by female Tenebrio molitor). The enantiomeric purities of the synthetic pheromone...
Article
Full-text available
To the human nose, mice produce unique, persistent and potent odour which is widely assumed to be derived mainly from their urine. In this review, we discuss why the mouse odour is so potent and long-lasting to the human nose. Sensory and chemical analyses have revealed that 2-sec-butyl-4,5-dihydrothiazole (SBT) was the major mousy odorant and pres...
Article
Unambiguous identification of isomeric lipids by mass spectrometry represents a significant analytical challenge in contemporary lipidomics. Herein, the combination of collision-induced dissociation (CID) with ozone-induced dissociation (OzID) on an ion-trap mass spectrometer is applied to the identification of triacylglycerol (TG) isomers that var...
Article
An asymmetric formal synthesis of azadirachtin, a potent insect antifeedant, was accomplished in 30 steps to Ley's synthetic intermediate (longest linear sequence). The synthesis features: 1) rapid access to the optically active right-hand segment starting from the known 5-hydroxymethyl-2-cyclopentenone scaffold; 2) construction of the B and E ring...
Article
Tandem Dess-Martin oxidation/Wittig reaction of (2Z,5Z)-2,5-octadien-1-ol yielded methyl (2E,4Z,7Z)-2,4,7-decatrienoate, a newly discovered pheromone component of the male dried bean beetle, while that of (±)-2,3-dodecadien-1-ol gave (±)-methyl (E)-2,4,5-tetradecatrienoate, the racemate of the known and major pheromone component. Methyl (2E,4E,7Z)-...
Article
Full-text available
The racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal 1, an odorant with a metallic blood smell, were synthesized. The detection threshold for humans was 0.019 ppb for (2E,4S,5S)-(−)-1 and 0.62 ppb for (2E,4R,5R)-(+)-1, respectively. The racemate (±)-1 made mice scared stiff at a dosage of approximately 1 mg, while the enantiomers were not...
Article
Male-specific volatile components, released by the dried bean beetle, Acanthoscelides obtectus, were identified as methyl (E,R)-2,4,5-tetradecatrienoate, methyl (2E,4Z,7Z)-2,4,7-decatrienoate, methyl (2E,4Z)-2,4-decadienoate, octadecanal and the sesquiterpenes (3Z,6E)- and (3E,6E)-α-farnesene. In olfactometer bioassays, pure methyl (E,R)-2,4,5-tetr...
Article
All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylh...
Article
Full-text available
Reproductive physiology in female mouse is profoundly affected by male odor. A well-known effect of male odor is the acceleration of puberty onset in prepubertal female mice exposed to male urine. Whether peripubertal exposure to male odor also influences female sexual behavior in adulthood is poorly known. Recently, we reported that female mice ex...
Article
Full-text available
Pheromonal communications are heavily dependent on the stereochemistry of pheromones. Their enantioselective syntheses could establish the absolute configuration of the naturally occurring pheromones, and clarified the unique relationships between absolute configuration and bioactivity. For example, neither the (R)- nor (S)-enantiomer of sulcatol,...
Patent
Full-text available
A compound represented by the following formula (1): wherein R1 is an aldopyranose residue wherein the 6-hydroxyl group is optionally alkylated, R2 is a C1-26 hydrocarbon group optionally having substituent(s), R3 is a hydrogen atom or a C1-26 hydrocarbon group optionally having substituent(s), R4 is a C1-21 hydrocarbon group optionally having sub...
Article
Pheromonal triacylglycerols and their analogs, 1A, 1B, 2A, 2B, 3A, 3B, and 3C, of male Drosophila fruit flies were synthesized and analyzed by GC-MS. Their GC retention times were found to be a reliable measure to analyze and identify these triacylglycerols with acetyl, oleoyl and tigloyl groups, although the stereoand regioisomers of 1 (1A and 1B)...
Article
Noncytotoxic anticancer α-galactosphingolipid agelasphin-9b (1) was isolated in 1993 from an Okinawan marine sponge. Since then, a large number of natural and synthetic glycolipids were bioassayed as immunostimulants, which activate natural killer T cells to generate cytokines such as interferon γ (IFN-γ) and interleukin 4 (IL-4). Some of them (2-6...
Article
Six samples [(3R,14R,26R)-, (3R,14S,26R)-, (3S,14R,26S)-, and (3S,14S,26S)-1, a mixture of (3R,14R,26S)- and (3S,14R,26R)-1, and a mixture of (3R,14S,26S)- and (3S,14S,26R)-1] of miyakosyne A [1, (4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol] were synthesized starting from the enantiomers of citronellal (2), employing olefin cross meta...
Article
Full-text available
2-(4-Hydroxyphenyl)naphthalene-1,8-dicarboxylic anhydride, a component of the phytoalexin that has been isolated from the peel of unripe banana (Musa acuminata), was synthesized from 3-bromoacenaphthene.
Article
Full-text available
Significance How sexual features and preferences originate and evolve is one of the most important and contentious problems in evolutionary biology. In some species, females choose male traits that indicate genetic quality or confer benefits. Thus, male traits and female preferences are assumed to originate at the same time and to coevolve. In cont...
Article
RCAI-147 is one of the hydroxylated analogues of KRN7000 which is known as a ligand for the activation of CD1d mediated invariant natural killer T cells (iNKT cells) and releases both T helper 1 (Th1) cytokines such as IFN-γ and T helper 2 (Th2) cytokines such as IL-4. KRN7000 has been anticipated as an antitumor drug or an adjuvant for viral infec...
Article
Full-text available
The exoskeletons of insects are covered by complex mixtures of cuticular hydrocarbons (CHCs) which are involved in social and sexual communication. However, little is known about the relationship between the structures of CHCs and their behavioral activity. The key component of the contact sex pheromone of the parasitoid Lariophagus distinguendus i...
Article
RCAI-80 is one of the ester analogs of KRN7000 (α-galactosylceramide). This compound released mainly T helper 2 (Th2) cytokines, such as IL-4 rather than T helper 1 (Th1) cytokines, such as IFNγ from the invariant natural killer T (iNKT) cells. In addition, it has been known that some of the hydroxylated derivatives of KRN7000 make the cytokine sec...
Patent
Full-text available
The invention provides esterified α-galactosylceramides effective for cancer treatment and the like, and a medicament containing same. In particular, the invention relates to a compound represented by the formula (I): wherein R1 is a hydrocarbon group having a carbon number of 1 to 30, R2 is a hydrocarbon group having a carbon number of 1 to 20, R...
Patent
Full-text available
The invention provides a glycolipid effective for cancer treatment and the like and a synthetic intermediate therefor, as well as a medicament containing the glycolipid and the like. The glycolipid is represented by the formula (1) or a salt thereof
Article
Full-text available
Eight analogues of (3R,11Z,19Z)-CH503 (3-acetoxy-11,19-octacosadien-1-ol), the anti-aphrodisiac pheromone of male Drosophila melanogaster, were synthesized for a bioassay. These were the enantiomers of 3-acetoxy-11,19-octacosadiyn-1-ol (1), 3-acetoxyoctacosan-1-ol (2), (Z)-3-acetoxy-11-octacosen-1-ol (3), and (Z)-3-acetoxy-19-octacosen-1-ol (4). No...
Conference Paper
Puberty onset in female mice is accelerated by male phero- mones. Whether peripubertal exposure to male odors also influences female sexual behavior in adulthood is at present unclear. We provide evidence that females exposed to male odors and thus showing puberty acceleration, displayed a preference for intact male over female or castrated mal...
Article
Full-text available
We synthesized seven new analogues of KRN7000: RCAI-133 and 154–159. RCAI-154, 156 and 158 are secondary-amide analogues having a hydroxy, a methyl or two methyl groups at the α-position of a linear C18-acyl chain, respectively. RCAI-155, 157 and 159 are corresponding N-methylated tertiary amide analogues, and RCAI-133 is the N-methylated KRN7000....
Article
KRN7000 is one of the α-galactosylceramides, which has a 2-hexacosanoylamino-3,4-dihydroxyoctadecyl group. This compound, known as a ligand for the activation of CD1d mediated invariant natural killer T cells (iNKT cells) which release both T helper 1 (Th1) cytokines such as IFNγ and Th2 cytokines such as IL-4, has been anticipated as an antitumor...
Article
We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by α-selective galactosylation of ceramide 9 with the 6-modified d-galactopyranosyl fluorides (8a-8f) or l-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demon...
Article
The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three well-established procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis,...
Article
The racemates and enantiomers of triglycerides 1a–e (2,3-ditigloyloxypropyl esters of palmitic, palmitoleic, stearic, oleic, and linoleic acids) of male Drosophila fruit flies were synthesized in three steps from the racemate and enantiomers of 2,3-acetoneglycerol (2) via 1-monoglycerides 4a–e derived from the above fatty acids. Appropriate conditi...
Article
Full-text available
Esterified ceramides, (2S,3R,4E)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3-diol (2) and (2S,3R,4E,6R)-2-[(30'-stearoyloxy)triacontanamido]octadec-4-ene-1,3,6-triol (4), are minor components of the human stratum corneum. We synthesized these ceramides by employing olefin cross metathesis as the key reaction for constructing their ω-hydro...
Article
Full-text available
The surface of insects is covered by a complex mixture of cuticular hydrocarbons (CHCs) to prevent desiccation. In many species these lipids also have communicative functions, but often it is unknown which components are crucial for the behavioural response. Furthermore, it is often ignored that polar lipids also occur on the insects' cuticle and m...
Article
Full-text available
(1R,7Z)-1-Methyl-7-hexadecenyl acetate (1), the female sex pheromone of the honey locust gall midge (Dasineura gleditchiae), was synthesized from 6-hepten-1-ol in an 8.9% overall yield (eight steps). Hydrolytic kinetic resolution of (±)-1,2-epoxy-8-heptadecyne was the key step in the synthesis.
Article
RCAI-84, 91, and 105-108 (1-6), the analogs of KRN7000 (A) with a ureido or a thioureido linkage instead of a carboxamido bond, were synthesized to examine their immunostimulatory activity against mouse lymphocytes. According to their bioassay, the ureido analog of KRN7000 [RCAI-105 (1)] and its 6'-O-methylated derivative [RCAI-106 (4)] induced a l...
Article
Full-text available
All the eight stereoisomers of 3-acetoxy-11,19-octacosadien-1-ol (1), the male sex pheromone (CH503) of Drosophila melanogaster, were synthesized from two acetylenic starting materials and the enantiomers of 3,4-epoxy-1-butanol PMB ether. Complete separation of the eight isomers of 1 by reversed phase HPLC at −20 °C was achieved after their esterif...
Article
(R)-10-Methyl-2-tridecanone, the female sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi Barber), was synthesized in 9 steps from methyl (S)-3-hydroxy-2-methylpropanoate in a 15.7% overall yield. Olefin cross metathesis between (R)-6-methyl-1-nonene and 5-hexen-2-one employing Grubbs' first-generation catalyst was the...
Article
The enantiomers of methyl (E)-2,4,5-tetradecatrienoate (1), a component of the male pheromone of Acanthoscelides obtectus, were synthesized from the enantiomers of 1-undecyn-3-ol (6), which were obtained via asymmetric acetylation of (±)-1-trimethylsilyl-1-undecyn-3-ol (4) with vinyl acetate as catalyzed by lipase PS (Amano). The ortho ester Claise...
Article
Full-text available
Colorado potato beetle, Leptinotarsa decem-lineata, is attracted to (S)-3,7-dimethyl-2-oxo-oct-6-ene-1,3-diol [(S)-CPB I], a male-produced aggregation pheromone. Pitfall trap studies were conducted to assess the relative attraction of L. decemlineata adults to synthetic mixtures of the (S)-and (R)-enantiomers of the phero-mone. Of the following ble...
Article
Full-text available
We report that the abdominal epidermis and associated tissues are the predominant sources of male-produced pheromones in the red flour beetle, Tribolium castaneum and, for the first time, describe the stereoisomeric composition of the natural blend of isomers of the aggregation pheromone 4,8-dimethyldecanal (DMD) in this important pest species. Qua...
Article
α-Galactosphingolipid analogues of KRN7000 with a sulfonamide (RCAI-39), a carbamate (RCAI-41), an α,α-difluorocarboxamide (RCAI-100) or an N-methylcarboxamide linkage (RCAI-127) instead of a carboxamide bond of KRN7000 were synthesized. Their bioactivities for mouse natural killer T cells were examined. Bioactivities of truncated analogues, OCH an...
Article
Contrary to the conventional wisdom that only pure enantiomers are bioactive, natural products with bioactivities are not always enantiomerically pure. For example, tribolure (4,8-dimethyldecanal), the aggregation pheromone of the red flour beetle, is a mixture of all the four stereoisomers in a ratio of (4R,8R)/.(4R,8S)/ (4S,8R)/ (4S,8S)= 4:4:1:1....
Article
Mori's synthetic works on bioactive natural products in general and pheromones in particular started about 40 years ago to establish their absolute configurations and also to clarify their stereochemistry-bioactivity relationships. Results indicate that bioactive natural products are not always enantiomerically pure, and the stereochemistry-bioacti...
Article
Full-text available
Protective group-free syntheses of four racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring were achieved in five or six steps from commercially available (±)-3-butyn-2-ol (6) and 2-alkenyl halides or 2-alken-1-ol by employing Lewis acid-catalyzed acetalization of δ, ε-epoxy ketones as the key reaction. (±)-Frontalin (1) was prepared in a...
Article
Both the crystalline enantiomers of 13-methylheptacosane, the female sex pheromone of Cacopsylla pyricola, were synthesized in gram quantities by starting from the enantiomers of citronellal, 1-bromodecane and 1-bromoundecane in 23–28% overall yield (eight steps).
Article
Chemistry of sphingolipids and glycosphingolipids is discussed with main emphasis on their synthetic methods. Microbial, plant, animal and marine sphingolipids and glycosphingolipids with the following biological roles are treated in this review: (i) inducers of fruiting body formation in Basidiomycetes, (ii) water barrier and supporting material o...
Article
Full-text available
The male-produced bicyclic acetal endo-brevicomin is a component of the pheromone blend that mediates colonization of host pines by the bark beetle Dendroctonus frontalis Zimmermann. Efforts to identify its behavioral function have been complicated by contrasting reports that it either enhances or reduces attraction of flying beetles. Our studies f...
Data
Full-text available
The banded pine weevil, Pissodes castaneus (De Geer, 1775) (Coleoptera, Curculionidae) is a forest pest recorded in Brazil since 2001, which is already distributed in the three states of the Southern Region, causing great concern to the forestry sector. Objectives of our study were to isolate, identify, and assess the behavioral activity of male-pr...
Article
All four stereoisomers of 4,8-dimethyldecanal (1) were synthesized from the enantiomers of 2-methyl-1-butanol and citronellal. Enantioselective GC analysis enabled separation of (4R,8R)-1 and (4R,8S)-1 from a mixture of (4S,8R)-1 and (4S,8S)-1, when octakis-(2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl)-γ-cyclodextrin was employed as a chiral...
Article
The racemate as well as both the enantiomers of sordidin (1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1]octane, 1) were synthesized, and the natural pheromone was shown to be (1S,3R,5R,7S)-(+)-1.