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Synthesis of biopterin and related pterin glycosides 査読

Tadashi Hanaya, Hiroshi Yamamoto

IUBMB Life 65 ( 4 ) 300 - 309 2013年4月

担当区分：筆頭著者記述言語：英語

Certain pterins having a hydroxyalkyl side chain at C-6 have been found as glycosidic forms in certain prokaryotes, such as 2'-O-(α-D-glucopyranosyl) biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium. Synthetic studies on glycosides of biopterin and related pterins have been made in view of the structural proof as well as for closer examination of their biological activities and functions. The syntheses of these natural pterin glycosides have effectively been achieved, mostly through appropriately protected N2-(N,N- dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl acceptors, and are reviewed here. © 2013 IUBMB Life.

DOI： 10.1002/iub.1137

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Inclusion complexation of 4′,6‑diamidino‑2‑phenylindole (DAPI) with cucurbit[7]uril and cyclodextrins (native β‑, 2,6‑di‑O‑methylated β‑, and γ‑cyclodextrin): characteristic inclusion behavior and fluorescence enhancement 査読

Y. Sueishi, S. Hagiwara, N. Inazumi, T. Hanaya

J. Incl. Phenom. Macrocycl. Chem. 99 ( 3-4 ) 209 - 216 2021年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：SPRINGER

Herein, we investigated the inclusion complexation of a fluorescent probe [4 ',6-diamidino-2-phenylindole (DAPI)] using various cyclodextrins (CDs) and cucurbit[7]uril (CB7). Using the continuous variation method, DAPI was found to form a 1:1 inclusion complex with CDs and CB7. H-1-NMR and 2D ROESY (H-1-H-1 rotating frame nuclear Overhauser effect) spectroscopy indicated that the inclusion of DAPI by the CDs and CB7 occurs via the encapsulation of the phenyl group and indole moiety of DAPI. The stability of the CB7 inclusion complex was higher than that of the CDs: the stability was attributed to the extra interaction formed between the dicationic dye (DAPI) and polar carbonyl groups at the portals of CB7. Furthermore, we determined the fluorescence quantum yield (phi) of the inclusion complexes. The phi values of DAPI were significantly enhanced upon its inclusion by CB7 and increased as the empirical solvent polarity parameter (E-T(30)) decreased. Based on these results, we concluded that the polarity of the microenvironment and protonation ability of the excited state of DAPI play important roles in emission efficiency.

DOI： 10.1007/s10847-020-01042-6

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Comparative study of inclusion complexation of tetraalkylphosphonium and ammonium salts with cucurbit[7]uril 査読

Y. Sueishi, S. Hagiwara, Y. Matsumoto, T. Hanaya

J. Incl. Phenom. Macrocycl. Chem. 98 117 - 122 2020年

Characterization of group‑inclusion complexations of rhodamine derivatives with native and 2,6‑di‑O‑methylated β‑cyclodextrins 査読

Y. Sueishi, Y. Matsumoto, Y. Kimata, Y. Osawa, N. Inazumi, T. Hanaya

J. Incl. Phenom. Macrocycl. Chem. 96 ( 3-4 ) 365 - 372 2020年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：SPRINGER

The inclusion complexations of rhodamine derivatives with native and 2,6-di-O-methylated beta-cyclodextrins (beta-CD and DM-beta-CD) were studied spectrophotometrically. Rhodamine derivatives were shown to form 1:1 inclusion complexes with beta-CDs by the continuous variation method. The structures of the inclusion complexes were characterized by H-1-H-1 rotating frame nuclear Overhauser effect spectroscopy (ROESY) NMR measurements. It was found that native beta-CD encapsulates the xanthenyl ring of rhodamines into the cyclodextrin cavity, while DM-beta-CD forms two group-in complexes (phenyl-in and xanthenyl-in (bidirectional (bimodal) inclusion complexes)) with rhodamines bearing moderately bulky functional groups. Furthermore, we demonstrated the unique thermodynamics for the group-inclusion complex formation by DM-beta-CD. The quantum yields for the inclusion complexes of rhodamines were determined using a quantum measurement apparatus equipped with a half-moon unit. The results indicated that the cyclodextrin inclusion of rhodamines with the bulky amino substituents on the xanthenyl ring largely decreases the quantum yield values. Based on these results, the substituent effects on the fluorescence process for the cyclodextrin inclusion complexes of rhodamines were discussed. This study provides useful insights for the functional group recognition of native and modified beta-CDs.

DOI： 10.1007/s10847-020-00979-y

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A comparative study on inclusion complexation of substituted anilinonaphthalene sulfonic acids with 1,6,20,25-tetraaza[6.1.6.1]-paracyclophane and β-cyclodextrin 査読

Y. Sueishi, A. Itoh, N. Inazumi, Y. Osawa, T. Hanaya

J. Incl. Phenom. Macrocycl. Chem. 91 ( 1-2 ) 1 - 7 2018年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：SPRINGER

The inclusion complexations of paracyclophane (CP44) and beta-cyclodextrin (beta-CD) with several anilinonaphthalene sulfonic acids (ANSs) have been characterized via the enhancement of fluorescence spectra upon inclusion. beta-CD and CP44 formed 1:1 inclusion complexes with ANSs, and the high stability of inclusion complexes of the latter was demonstrated. The thermodynamic parameters observed from the temperature dependence of the inclusion constants (van't Hoff analysis) showed that CP44 inclusion complexations with ANSs are enthalpy-driven. Furthermore, the structure of the inclusion complexes was discussed based on H-1- and 2D ROESY-NMR measurements. It was found that CP44 encapsulates the naphthalene moiety of ANSs. On the other hand, differences in the structures of the beta-CD inclusion complexes were observed for the 4-OH-substituted ANS. The molecular recognition for the inclusion of beta-CD was found to be sensitive compared with that of CP44. In addition, the local polarity inside the CP44 and beta-CD cavities was evaluated using ANSs as the fluorescence probe. Based on these results, we have suggested that the local polarity of ANSs in the hydrophobic cavities of CP44 and beta-CD plays an important role in quantum yield enhancement upon inclusion.

DOI： 10.1007/s10847-018-0790-4

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Characterization of inclusion complexation of various tetraalkylammonium chlorides with cucurbit[7]uril by external highpressure studies 査読

Y. Matsumoto, N. Inazumi, T, Hanaya, Y. Sueishi

J. Incl. Phenom. Macrocycl. Chem. 92 ( 1-2 ) 205 - 210 2018年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：SPRINGER

The inclusion constants of tetraalkylammonium salts (ASs) with cucurbit[7]uril (CB[7]) were determined at high-pressures using methylene blue as a chemical indicator. CB[7] formed 1:1 inclusion complexes with ASs. We found a characteristic dependence of the alkyl chain substituents in ASs on the inclusion equilibrium, which was responsible for the formation of clathrate hydrates of the AS in bulk. Furthermore, we examined the effects of external high pressures on the CB[7] inclusion complexations of ASs having different alkyl chain lengths. Pressure dependence experiments allowed us to calculate the reaction volume (Delta V) upon inclusion; i.e., the volume change (Delta V (desolv)) accompanying desolvation around the guest molecules and the volume change (Delta V (repel)) caused by the water molecules repelled from the CB[7] cavity. The volumetric study for the inclusion of ASs with CB[7] showed that in the tetraheptylammonium ion, one arm (alkyl chain) was encapsulated in the CB[7] cavity, while in other ASs, two arms were located in the cavity. NMR measurements of the complexes and pressure-dependent studies provided unique information on the structures of the inclusion complexes of ASs with CB[7].

DOI： 10.1007/s10847-018-0832-y

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Efficient Total Syntheses of Natural Neopterin Glycosides: Neopterin Glucronide and Solfapterin 査読

T. Hanaya, K. Iwasaki, K, Saeki, T. Hattori

Heterocycles 95 390 - 409 2017年

Inclusion complexation abilities of cucurbit[6]uril for various aromatic amines in the presence of alkali metal cations 査読

Yusaku Honda, Tadashi Hanaya, Yoshimi Sueishi

J. Incl. Phenom. Macrocycl. Chem. 88 253 - 257 2017年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：SPRINGER

The inclusion complexation of aromatic amines with cucurbit[6]uril (CB[6]) capped with alkali metal cations was studied spectrophotometrically. We showed that CB[6] capped with alkali metal cations forms a 1:1 inclusion complex with the aromatic amine guests (neutral organic molecules), independent of the length of guest molecules. The effects of salts on the inclusion constants of CB[6] in the presence of different alkali salts were examined and it was found that the inclusion constants increased in the order of alkali cation Cs+ < Na+ < K+, suggesting the interaction of amine guests with the capped alkali metal cation. Further, the structures of the inclusion complexation of aromatic amines with CB[6] were characterized by H-1 NMR measurements. Based on the results, the inclusion abilities of CB[6] capped with alkali metal cations are discussed.

DOI： 10.1007/s10847-017-0727-3

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Influence of Counter Anions on Inclusion Complexation of p-Sulfonatocalix[6] arene with 1-Butyl-3-methylimidazolium Salts (Ionic Liquids) 査読

Yusaku Honda, Shono Fujitani, Sho Tamaki, Naoya Inazumi, Tadashi Hanaya, Yoshimi Sueishi

ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-INTERNATIONAL JOURNAL OF RESEARCH IN PHYSICAL CHEMISTRY & CHEMICAL PHYSICS 230 ( 8 ) 1153 - 1164 2016年8月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：WALTER DE GRUYTER GMBH

Using the inclusion complexation of methylene blue with p-sulfonatocalix[ 6] arene (Calix-S6) as a chemical indicator, the association constants of inclusion complexes of Calix-S6 with visible-spectroscopically inert 1-butyl-3-methylimidazolium salts (ionic liquids (IL): counter anions BF4-, PF6-, and Cl-) were determined. It was found that the experimentally observed association constants of IL with Calix-S6 in a water-methanol mixture increased in the order of counter anion Cl- < BF4- < PF6-. The F-19 NMR signals of counter anions BF4- and PF6- shift upfield upon addition of Calix-S6. From the F-19 NMR chemical shifts, we suggested that Calix-S6 forms weak 1 : 1 complexes with the BF4- and PF6- anions. The binding constants and their thermodynamic parameters for the complexation of the BF4- and PF6- anions with Calix-S6 were evaluated in a water-methanol mixture (6 : 4 (V/V)) at 298 K:K-A = 26.2M (-1) for BF4- and 106 M-1 for PF6 (-). Based on the results, the characteristics for the complexation of the counter anions with Calix-S6 were discussed and the inclusion constants of Calix-S6 with the cationic ringmoiety of 1-butyl-3-methyl-imidazolium salts were determined.

DOI： 10.1515/zpch-2015-0611

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Investigation of inclusion complexation of imidazolium and pyrrolidinium chlorides with water-soluble p-sulfonatocalix[6]arene: characteristic effects of external pressure, temperature, and substituents 査読

Yoshimi Sueishi, Yusaku Honda, Shono Fujitani, Naoya Inazumi, Tadashi Hanaya

J. Incl. Phenom. Macrocycl. Chem. 86 255 - 261 2016年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：SPRINGER

Using the inclusion complexation of methylene blue as a chemical indicator, the inclusion constants of imidazolium and pyrrolidinium chlorides (ionic liquids (IL)) with p-sulfonatocalix[6]arene (Calix-S6) were determined in a water-methanol mixture. In the inclusion of imidazolium chlorides, we found the characteristic inclusion constants, dependent on the length of the alkyl side chain. From the temperature effect on the inclusion, the differences in the inclusion interactions of imidazolium and pyrrolidinium ring moiety with the sulfonate groups of the Calix-S6's portal were observed. Further, from high-pressure studies on the inclusion complexation, the volume changes caused by the conformational changes of Calix-S6 and desolvation around the guest and host molecules upon inclusion were evaluated. Based on the results, we demonstrated that the volume change related to desolvation upon inclusion plays an important role in the reaction volume for the inclusion equilibrium of IL with Calix-S6. The structures of the inclusion complexes were established from 2D ROESY NMR measurements and a volumetric study of the inclusion complexation with p-sulfonated Calix-S6 having a flexible cavity was performed.

DOI： 10.1007/s10847-016-0660-x

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Characteristically Steric Effects of Substituent on Bidirectional Inclusion Complexation of α-Substituted Phenyl-2,4,6-trimethoxybenzyl(t-butyl)nitroxides with β-Cyclodextrins 査読

K. Miyazono, T. Hanaya, Y. Sueishi

J. Incl. Phenom. Macrocycl. Chem. 83 ( 1-2 ) 193 - 197 2015年10月

Characteristic effects of substituent and external pressure on group- inclusion complexation with p-sulfonatocalix[8]arene and gamma-cyclodextrin 査読

Keitaro Miyazono, Tadashi Hanaya, Yoshimi Sueishi

HIGH PRESSURE RESEARCH 34 ( 3 ) 337 - 344 2014年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：TAYLOR & FRANCIS LTD

By synthesizing unique nitroxide probes (alpha-substituted phenyl-2,4,6-trimethoxybenzyl(t-butyl) nitroxide), we have shown that p-sulfonatocalix[8]arene (Calix-S8) and gamma-cyclodextin (gamma-CD) form electron spin resonance spectroscopically separable group-inclusion complexes (alpha-substituted phenyl-in (R-in) and t-butyl-in complexes) and determined the group-inclusion constants of Calix-S8 and gamma-CD. Using nitroxide probes, we have examined the effects of substituent and external pressure on group-inclusion complexation with Calix-S8 and gamma-CD. Experiments on pressure dependence enabled us to calculate the reaction volume (Delta V) for R-in and t-butyl-in complex formations. Delta V for group-in complexation with Calix-S8 had negative values. In contrast, Delta V values for gamma-CD showed positive values, which is responsible for the repelled water molecules in the CD cavity. The characteristic pressure effects on group-in complexation suggest that group recognition by gamma-CD is sensitive when compared with that by Calix-S8.

DOI： 10.1080/08957959.2014.947605

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Selective Preparation of 6- and 7-(Polyhydroxypropyl)pterins from Pentos-2-uloses 査読

T. Hanaya, K. Ito

Heterocycles 88 1491 - 1499 2014年

First synthesis of asperopterin A, an isoxanthopterin glycoside from Aspergillus oryzae 査読

Tadashi Hanaya, Hiroshi Yamamoto

PTERIDINES 24 ( 1 ) 3 - 6 2013年6月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：INT SOC PTERIDINOLOGY

The key precursor, N-2-(N,N -dimethylaminomethylene)-6-hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (16) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (5) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (12), followed by the protection of the pteridine ring. Glycosylation of 16 with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (18) in the presence of tin(IV) chloride yielded the corresponding beta-D-ribofuranoside. Successive removal of the protecting groups of the resulting D-ribofuranoside provided asperopterin A (4b).

DOI： 10.1515/pterid-2013-0005

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SYNTHESIS OF 2-ACETAMIDO-2,5-DIDEOXY-5-PHOSPHORYL-D-GLUCOPYRANOSE DERIVATIVES: NEW PHOSPHA-SUGAR ANALOGS OF N-ACETYL-D-GLUCOSAMINE 査読

Tadashi Hanaya, Masahiro Kawaguchi, Masakazu Sumi, Kazuo Makino, Keiko Tsukada, Hiroshi Yamamoto

HETEROCYCLES 86 ( 2 ) 1147 - 1165 2012年12月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).

DOI： 10.3987/COM-12-S(N)69

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SYNTHETIC STUDIES ON NATURAL PTERIN GLYCOSIDES 招待査読

Tadashi Hanaya, Hiroshi Yamamoto

Heterocycles 85 2375 - 2390 2012年

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

Some pterins having various kind of sugars attached to the hydroxyalkyl side-chain at C-6 are known to occur in certain prokaryotes as exemplified by 2'-O-(alpha-D-glucopyranosyl)biopterin isolated from various kinds of cyanobacteria. A synthetic exploration of various types of glycosides of biopterin and related pterins has been undertaken owing to a marked interest in their physiological functions and biological activities as well as the structural proof of those natural products. This review summarizes our synthetic studies on natural pterin glycosides by employing the appropriately protected N-2-(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]pterin derivatives as glycosyl accepters.

DOI： 10.3987/REV-12-742

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FIRST SYNTHESIS OF A NATURAL ISOXANTHOPTERIN GLYCOSIDE, ASPEROPTERIN-A 査読

Tadashi Hanaya, Kazumasa Ejiri, Hiroshi Yamamoto

HETEROCYCLES 84 801 - 813 2012年

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

The key precursor, N-2-(N,N-dimethylaminomethylene)-6-hydroxymethy1-8-methyl-3[2-(4-nitrophenypethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylam1no-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5-tri-O-benzoy1-beta-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.

DOI： 10.3987/COM-11-S(P)57

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AN EFFICIENT SYNTHESIS OF ANTIBIOTIC SF-2312 (3-DIHYDROXYPHOSPHORYL-1,5-DIHYDROXY-2-PYRROLIDONE) 査読

Tadashi Hanaya, Chika Itoh

Heterocycles 82 1675 - 1683 2011年

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：PERGAMON-ELSEVIER SCIENCE LTD

N-Benzyloxy-2-(diethoxyphosphoryl)pent-4-enamide (6) was prepared from ethyl diethoxyphosphorylacetate in a 3-step sequence. Oxidative cleavage of the terminal olefin of 6 with osmium tetroxide and sodium periodate afforded 1-benzyloxy-3-diethoxyphosphoryl-5-hydroxy-2-pyrrolidone (7). The first synthesis of racemic SF-2312 was achieved by treatment of 7 with trimethylsilyl bromide, followed by hydrogenolysis.

DOI： 10.3987/COM-10-S(E)80

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Synthesis of 6-hydroxymethylpterin α- and β-D-glucosides 査読

T. Hanaya, H. Baba, K. Ejiri, H. Yamamoto

Heterocycles 80 1013 - 1025 2010年

First Synthesis of a Natural Neopterin Glycoside: 3’-O-(β-D-Glucopyranosyluronic acid)neopterin 査読

T. Hanaya, T. Hattori, D. Takayama, H. Yamamoto

Pteridines 21 79 - 83 2010年

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