- N-Phenylacetylation and Nonribosomal Peptide Synthetases with Substrate Promiscuity for Biosynthesis of Heptapeptide Variants, JBIR-78 and JBIR-95
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JBIR-78 (1) and JBIR-95 (2), both of which are heptapeptide derivatives isolated from Kibdelosporangium sp. AK-AA56, have the same amino acid sequences except for the second amino acid: phenylacetic acid (Paa)-l-Val-d-Asp (1)/d-cysteic acid (2)-l-Ala-(3S)-3-hydroxy-d-Leu-Gly-d-Ala-l-Phe. Heterologous expression of the biosynthetic gene cluster including genes encoding nonribosomal peptide synthetases (NRPS) and in vitro assays with recombinant Orf3, an l-cysteic acid synthase homologue, suggested the single A domain in module 2 activates both l-Asp and l-cysteic acid to yield 1 and 2, respectively, although the substrate specificities of the A domains of NRPSs are usually strict. Biosynthetic mechanism of introduction of N-terminal Paa was also investigated. Recombinant Orf1 and Orf2 similar to subunits of pyruvate dehydrogenase complex catalyzed the conversion of phenylpyruvate into phenylacetyl-CoA together with dihydrolipoyl dehydrogenase whose encoding gene is located outside of the gene cluster. Moreover, we showed that phenylacetyl-CoA was directly condensed with l-Val, which was tethered to a peptidyl carrier protein, at the first condensation domain in the NRPS.
- Takeda, Kunpei,Kemmoku, Kohei,Satoh, Yasuharu,Ogasawara, Yasushi,Shin-Ya, Kazuo,Dairi, Tohru
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p. 1813 - 1819
(2017/07/26)
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- Synthesis of sulfonyl chlorides and sulfonic acids in SDS micelles
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H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and di-sulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity. Georg Thieme Verlag Stuttgart · New York.
- Bahrami, Kiumars,Khodaei, Mohammad M.,Abbasi, Jamshid
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experimental part
p. 316 - 322
(2012/03/26)
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- Formation of the bisulfite anion (HSO3 -, m/z 81) upon collision-induced dissociation of anions derived from organic sulfonic acids
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In the negative-ion collision-induced dissociation mass spectra of most organic sulfonates, the base peak is observed at m/z 80 for the sulfur trioxide radical anion (SO3 -·). In contrast, the product-ion spectra of a few sulfonates, such as cysteic acid, aminomethanesulfonate, and 2-phenylethanesulfonate, show the base peak at m/z 81 for the bisulfite anion (HSO3 - ). An investigation with an extensive variety of sulfonates revealed that the presence of a hydrogen atom at the β-position relative to the sulfur atom is a prerequisite for the formation of the bisulfite anion. The formation of HSO3 - is highly favored when the atom at the β-position is nitrogen, or the leaving neutral species is a highly conjugated molecule such as styrene or acrylic acid. Deuterium-exchange experiments with aminomethanesulfonate demonstrated that the hydrogen for HSO3 - formation is transferred from the β-position. The presence of a peak at m/z 80 in the spectrum of 2-sulfoacetic acid, in contrast to a peak at m/z 81 in that of 3-sulfopropanoic acid, corroborated the proposed hydrogen transfer mechanism. For diacidic compounds, such as 4-sulfobutanoic acid and cysteic acid, the m/z 81 ion can be formed by an alternative mechanism, in which the negative charge of the carboxylate moiety attacks the α-carbon relative to the sulfur atom. Experiments conducted with deuterium-exchanged and deuterium-labeled analogs of sulfocarboxylic acids demonstrated that the formation of the bisulfite anion resulted either from a hydrogen transfer from the β-carbon, or from a direct attack by the carboxylate moiety on the α-carbon. Copyright
- Jariwala, Freneil B.,Wood, Ryan E.,Nishshanka, Upul,Attygalle, Athula B.
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experimental part
p. 529 - 538
(2012/08/28)
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- Thailandepsins: Bacterial products with potent histone deacetylase inhibitory activities and broad-spectrum antiproliferative activities
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Histone deacetylase (HDAC) inhibitors have emerged as a new class of anticancer drugs, with one synthetic compound, SAHA (vorinostat, Zolinza; 1), and one natural product, FK228 (depsipeptide, romidepsin, Istodax; 2), approved by FDA for clinical use. Our studies of FK228 biosynthesis in Chromobacterium violaceum no. 968 led to the identification of a cryptic biosynthetic gene cluster in the genome of Burkholderia thailandensis E264. Genome mining and genetic manipulation of this gene cluster further led to the discovery of two new products, thailandepsin A (6) and thailandepsin B (7). HDAC inhibition assays showed that thailandepsins have selective inhibition profiles different from that of FK228, with comparable inhibitory activities to those of FK228 toward human HDAC1, HDAC2, HDAC3, HDAC6, HDAC7, and HDAC9 but weaker inhibitory activities than FK228 toward HDAC4 and HDAC8, the latter of which could be beneficial. NCI-60 anticancer screening assays showed that thailandepsins possess broad-spectrum antiproliferative activities with GI50 for over 90% of the tested cell lines at low nanomolar concentrations and potent cytotoxic activities toward certain types of cell lines, particularly for those derived from colon, melanoma, ovarian, and renal cancers. Thailandepsins thus represent new naturally produced HDAC inhibitors that are promising for anticancer drug development.
- Wang, Cheng,Henkes, Leonhard M.,Doughty, Leah B.,He, Min,Wang, Difei,Meyer-Almes, Franz-Josef,Cheng, Yi-Qiang
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supporting information; experimental part
p. 2031 - 2038
(2011/12/15)
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- Grassypeptolides A-C, cytotoxic bis-thiazoline containing marine cyclodepsipeptides
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Grassypeptolides A-C (1-3), a group of closely related bis-thiazoline containing cyclic depsipeptides, have been isolated from extracts of the marine cyanobacterium Lyngbya confervoides. Although structural differences between the analogues are minimal, comparison of the in vitro cytotoxicity of the series revealed a structure-activity relationship. When the ethyl substituent of 1 is changed to a methyl substituent in 2, activity is only slightly reduced (3-4-fold), whereas inversion of the Phe unit flanking the bis-thiazoline moiety results in 16-23-fold greater potency. We show that both 1 and 3 cause G1 phase cell cycle arrest at lower concentrations, followed at higher concentrations by G2/M phase arrest, and that these compounds bind Cu2+ and Zn 2+. The three-dimensional structure of 2 was determined by MS, NMR, and X-ray crystallography, and the structure of 3 was established by MS, NMR, and chemical degradation. The structure of 3 was explored by in silico molecular modeling, revealing subtle differences in overall conformation between 1 and 3. Attempts to interconvert 1 and 3 with base were unsuccessful, but enzymatic conversion may be possible and could be a novel form of activation for chemical defense.
- Kwan, Jason C.,Ratnayake, Ranjala,Abboud, Khalil A.,Paul, Valerie J.,Luesch, Hendrik
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experimental part
p. 8012 - 8023
(2011/03/20)
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- Alotamide A, a novel neuropharmacological agent from the marine cyanobacterium Lyngbya bouillonii
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Alotamide A (1), a structurally Intriguing cyclic depsipeptide, was isolated from the marine mat-forming cyanobacterlum Lyngbya bouillonii collected In Papua New Guinea. It features three contiguous peptidic residues and an unsaturated heptaketide with oxidations and methylations unlike those found In any other marine cyanobacterial metabolite. Pure alotamide A (1) displays an unusual calcium influx activation profile In murine cerebrocortical neurons with an EC50 of 4.18 uU.
- Soria-Mercado, Irma E.,Pereira, Alban,Cao, Zhengyu,Murray, Thomas F.,Gerwick, William H.
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supporting information; experimental part
p. 4704 - 4707
(2009/12/26)
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- Kinetics of oxidation of L-cystine by pyridinium bromochromate
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The kinetics of oxidation of cystine by pyridinium bromochromate (PBC) was studied spcctrophotometrically under pseudo-first order conditions in perchloric acid medium at 370 nm. It was found that the reaction is first order in [PBC], fractional order in [cystine] and the reaction rate is increased with [H +] showing an order of more than unity. Product analysis confirmed cysteic acid as the final product of oxidation.
- Annapurna,Kumar, A. Kalyan,Vani,Rao, G. Nageswara
-
body text
p. 542 - 545
(2009/07/18)
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- Functional group requirements within the peptide H-Pro-Pro-Asp-NH2 as a catalyst for aldol reactions
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H-Pro-Pro-Asp-NH2 1 is a versatile catalyst for asymmetric aldol reactions. In this work, the functional group tolerance within the catalyst structure has been examined. Several analogs of H-Pro-Pro-Asp-NH2 in which the N-terminal secondary amine or the carboxylic acid in the side chain of the aspartic acid residue is replaced by different functional groups were prepared. Evaluation of their catalytic properties revealed that both the N-terminal secondary amine and the carboxylic acid are important for catalysis. The implications for the reaction mechanism are discussed.
- Revell, Jefferson D.,Wennemers, Helma
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p. 8420 - 8424
(2008/02/08)
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- Synthesis of L-cysteine and L-cysteic acid by paired electrolysis method
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L-Cysteine and L-cysteic acid were synthesized by paired eletrolysis method. A high purity over 98% and high yield over 90% of both products were gained. When current density was 7 A/dm2 and concentration of L-cysteine was 0.6 mol/dm3, the highest current efficiency of anode and cathode was achieved. Total current efficiency was over 180%. The cyclic voltammetry behaviors of hydrobromic acid and cystine showed that a typical EC reaction took place in the anodic cell. The anode reaction and successive chemical reaction accelerated each other to get a high speed and current efficiency.
- Wang, Xixin,Zhao, Jianling
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p. 332 - 333
(2007/10/03)
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- Antioxidant chemistry: Oxidation of L-cysteine and its metabolites by chlorite and chlorine dioxide
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The oxidation of L-cysteine and its metabolites cystine and L-cysteinesulfinic acid by chlorite and chlorine dioxide has been studied in unbuffered neutral and slightly acidic media. The stoichiometry of the oxidation of L-cysteine was deduced to be 3ClO2- + 2H 2NCH(COOH)CH2SH → 3Cl- + 2H 2NCH(COOH)CH2SO3H with the final product as cysteic acid. The stoichiometry of the chlorite-cysteinesulfinic acid gave a ratio of 1:2, ClO2- + 2H2NCH(COOH)CH 2SO2H → Cl- + 2H2NCH(COOH) CH2SO3H. There was no further oxidation past cysteic acid, and there was no evidence of sulfate formation which would have indicated the cleavage of the carbon-sulfur bond. The reaction is oligooscillatory in chlorine dioxide formation. In conditions of excess oxidant, the reaction is characterized by a short induction period followed by a rapid and autocatalytic formation of chlorine dioxide. Chlorine dioxide is formed by the reaction of intermediate HOCl with the excess chlorite: 2ClO2- + 2HOCl + H- → 2ClO2(aq) + Cl- + H2O. Oligooscillations observed in chlorine dioxide formation result from the competition between this pure oxyhalogen reaction and reactions that consume chlorine dioxide. The rate of the reaction of chlorine dioxide with cysteine and its metabolites is fast and is of comparable magnitude with the reactions that form chlorine dioxide. The reaction of chlorine dioxide with L-cysteine is first order in both oxidant and substrate, retarded by acid, and has a lower-limit bimolecular rate constant of 405 ± 50 M-1 s-1, while for the reaction with L-cysteinesulfinic acid the rate constant is 210 ± 15 M-1 s-1. It would appear that the existence of a zwitterion on the asymmetric carbon atom precludes the formation of N-chloramines as has been observed with taurine and aminomethanesulfonic acid. The mechanism for the reaction is satisfactorily described by a network of 28 elementary reactions which include autocatalysis by HOCl.
- Darkwa, James,Olojo, Rotimi,Chikwana, Edward,Simoyi, Reuben H.
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p. 5576 - 5587
(2007/10/03)
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- Chemical properties of N-chlorotaurine sodium, a key compound in the human defence system
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N-Chlorotaurine (NCT) is known to play an important role in the human defence system. The already proved utility of the sodium salt as a disinfectant in human medicine suggested a thorough investigation of its chemical properties. Chlorine transfer to N-H groups (transhalogenation) and oxidation of thio and aromatic compounds represent its main reactions. Auto-chlorination causes disproportionation forming N,N-dichlorotaurine (NDCT) with Kd = [NDCT][taurine]/fa[NCT]2 aH+ = (4.5 ± 0.8) times; 106, while the reaction with ammonium releasing NH2Cl is characterised by KNHC2 = [NH2Cl][taurine]/[NCT][NH4+] fa2 = 0.02 ± 0.004. The verified unique stability and low-level reactivity of NCT are considered essential for its function in the mammalian defence system and its practical applicability, which manifests itself in an optimal compromise between microbicidal activity and toxicity.
- Gottardi, Waldemar,Nagl, Markus
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p. 411 - 421
(2007/10/03)
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- A new and expeditious asymmetric synthesis of (R)- and (S)-2-aminoalkanesulfonic acids from chiral amino alcohols
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The mechanism for the transformation of β-amino alcohol methanesulfonate hydrochlorides into sodium β-amino alkanesulfonates using sodium sulfite was investigated. The results show that sodium sulfite initially neutralizes the β-amino alcohol methanesulfonate hydrochloride to give a free β-amino alcohol methanesulfonate, which then cyclizes to a 2-alkylaziridine. Attack by the previously formed sodium bisulfite at the less hindered carbon atom of the aziridine ring then yields a β-amino alkanesulfate sodium salt. Based on this mechanistic proposal, a new and rapid asymmetric synthesis of (R)- and (S)-2-aminoalkanesulfonic acids from chiral amino alcohols was developed. Chiral amino alcohols were converted to chiral aziridines through the Wenker method or Mitsunobu reaction and the resulting aziridines were reacted with sodium bisulfite to produce chiral β-amino alkanesulfonic acids.
- Xu, Jiaxi
-
p. 1129 - 1134
(2007/10/03)
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- First steps in the oxidation of sulfur-containing amino acids by hypohalogenation: Very fast generation of intermediate sulfenyl halides and halosulfonium cations
-
Sulfur-containing amino acids show an extraordinary binding towards HOCl/ClO-. During the process, the Cl is transferred from the O to the S of the amino acid. Met reacts with HOCl one order of magnitude faster than the non-S containing amino acids (k((Met+HOCl))=8.7 · 108 mol-1 dm3 s-1). Instead, Cys reacts as its thiolate (RS-), two orders-of-magnitude faster (k((RS- +HOCl))=1.2 · 109 mol-1 dm3 s-1). Cys reacts also with ClO- (k((RS- +ClO-))=1.9 · 105 mol-1 dm3 s-1). Such processes take place much more readily than the corresponding N-halogenation of the non-sulfur containing amino acids. To our knowledge, these are the first kinetic measurements of the rate of formation of sulfenyl halides and halosulfonium cations in aqueous solution. Sulfenyl chlorides and chlorosulfonium ions derived from amino acids are elusive, and sulfide-type amino acids (Met) eventually yield sulfoxides (MetO), while thiol-type amino acids (Cys) lead to disulfides (Cys/Cys) and sulfonic acids (Cya). The fate of sulfur- containing amino acids upon oxidation with HOCl/ClO- seems to be related to their mutagen-inactivation ability. (C) 2000 Elsevier Science Ltd.
- Armesto,Canle L.,Fernández,García,Santaballa
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p. 1103 - 1109
(2007/10/03)
-
- Kinetics and mechanism of the reactions of superoxochromium(III) ion with biological thiols
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The kinetics of the oxidation of three biological thiols (L-cysteine, glutathione, and DL-penicillamine) to their sulfinic and sulfonic acid derivatives by CrOO2+ in aqueous perchloric acid and in the presence of 2-propanol have been studied spectrophotometrically with the aid of the initial-rates method. The kinetic order of the oxidant is 2, whereas that of the reductant is not defined. The acidity of the medium has a slight effect on the initial rates (acid catalysis for both L-cysteine and DL-penicillamine and base catalysis for glutathione). An increase of the ionic strength leads to a rise of the initial rate for both L-cysteine and DL-penicillamine, whereas the initial rate for glutathione is insensitive to the ionic strength. The reactions are inhibited by both 2-propanol and dissolved O2 and catalyzed by Mn2+, whereas Ce3+ has almost no effect on them. At low 2-propanol concentration and in the absence of Mn2+ the initial rate vs temperature plots have a minimum at around 20 °C, whereas in the presence of either concentrated 2-propanol or Mn2+ the Arrhenius law is fulfilled. A single mechanism is proposed for the three reactions involving a CrOO2+/thiol complex, CrOOH2+, and CrO2+ as intermediates. The bimolecular rate constants for the reactions of the intermediate CrO2+ with L-cysteine and DL-penicillamine at 25.0 °C have been obtained (around 103 M-1 s-1 in both cases). Some kinetic data for the decomposition of CrOO2+ in the absence of thiol are also given.
- Perez-Benito, Joaquin F.,Arias, Conchita
-
p. 5837 - 5845
(2007/10/03)
-
- Studies on the aerobic photooxidation of cysteine using riboflavin as a sensitizer: Evidence for the photogeneration of a superoxide anion and hydrogen peroxide
-
The riboflavin sensitized oxidation of cysteine under an aerobic condition was investigated. The effects of various scavengers, such as superoxide dismutase, catalase, mannitol, sodium azide and potassium ferrocyanide (an electron donor), on the photooxidation were determined. A reaction mechanism involving the superoxide anion is proposed for the photooxidation of cysteine to cysteic acid.
- Sarkar, Biswajit,Das, Utpal,Bhattacharyya, Subirnath,Bose, Swapan K.
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p. 910 - 912
(2007/10/03)
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- Homogeneous Aqueous Oxidation of Organic Molecules by OxoneR and Catalysis by a Water-Soluble Manganese Porphyrin Complex
-
Peroxymonosulfate (KHSO5) oxidizes a wide variety of water-soluble organic molecules in aqueous solutions, and the reactions are generally more rapid in phosphate buffer (pH 6-7) than in pure water.A water-soluble porphyrin complex, meso-tetrakis(4-N-methylpyridyl)porphyrinatomanganese(III) chloride, catalyzes epoxidation and hydroxylation under neutral pH conditions.
- Zheng, Tu-Cai,Richardson, David E.
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p. 833 - 836
(2007/10/02)
-
- Manganese Porphyrin Catalyzed Homogeneous Aqueous Oxidation of Organic Molecules by Magnesium Monoperoxyphthalate (MMPP)
-
Magnesium monoperoxyphthalate (MMPP) oxidizes a variety of organic molecules in neutral homogeneous aqueous solutions at room temperature.A water-soluble porphyrin complex, meso-tetrakis-(4-N-methylpyridyl)porhyrinatomanganese(III) chloride, Mn(III)TMPyP(4) Cl, acts as an efficient catalyst for the epoxidation and hydroxylation of water-soluble hydrocarbons.
- Zheng, Tu-Cai,Richardson, David E.
-
p. 837 - 840
(2007/10/02)
-
- Synthesis of l-cysteic acid by indirect electrooxidation and an example of paired synthesis: L-cysteic and l-cysteine from l-cystine
-
This paper studies the synthesis of 1-cysteic acid from 1-cystine by oxidation with electrochemically generated bromine in aqueous-HBr solution. High current efficiency and material yield were obtained. A very interesting process of paired synthesis has been proposed to obtain 1-cysteic acid and 1-cysteine from cystine that improves notably the economical parameters.
- Sanchez-Cano,Montiel,Aidaz
-
p. 877 - 886
(2007/10/02)
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- Formaldehyde Dehydrogenase from Pseudomonas putida: The Role of A Cysteinyl Residue in the Enzyme Activity
-
Formaldehyde dehydrogenase from Pseudomonas putida C-83 was found to contain 7 half-cystine residues per subunit monomer, as checked by the method of performic acid oxidation.Approximately 7 sulfhydryl groups per subunit monomer were titrated with 5,5'-dithiobis(2-nitrobenzoic acid) (DTNB) after denaturation with 8 M urea.In the native enzyme, modification of three sulfhydryl groups per subunit with p-chloromercuribenzoate (PCMB) led to the complete loss of enzyme activities for both formaldehyde and n-butanol.Hydrogen-peroxyde competitively inhibited the enzyme activity for formaldehyde, while it was only slightly inhibitory to the activity for n-butanol.Both formaldehyde and hydrogen-peroxide protected one sulfhydryl group per subunit monomer from modification with PCMB.Moreover, hydrogen-peroxide was hardly reactive to the enzyme which was preincubated with formaldehyde.From these observations, we conclude that one of three PCMB-reactive sylfhydryl groups is essential for the binding of formaldehyde, and hydrogen-peroxide modifies this sulfhydryl group.
- Ogushi, Susumu,Ando, Makoto,Tsuru, Daisuke
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p. 2503 - 2508
(2007/10/02)
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- Oxidation of Thiols by Superoxide Ion
-
Superoxide ion oxidizes aromatic thiols to disulfides or sulfonic acids.Benzene-1,2-dithiol and its 4-methyl analogue formed the cyclic disulfides dibenzotetrathiocins.Aliphatic thiols gave disulfides, and ethane-1,2-dithiol and propane-1,3-dithiol formed the cyclic disulfides 1,2,5,6- tetrathiocan and 1,2,6,7-tetrathiecan respectively.Butane-1,4-dithiol underwent an intramolecular cyclization to 1,2-dithian.Cysteine was oxidized by O2 anion radical to cysteic acid.
- Crank, George,Makin, Mohammad I. H.
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p. 2331 - 2337
(2007/10/02)
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- Etude cinetique des reactions du vanadium (V) avec la cysteine
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Vanadium V(V) is reduced to V(IV) with the production of cystine in the presence of thioaminoacid if this is in excess.If this is not the case, two successive reactions are observed leading to the formation of sulfinic and sulfonic acid derivative of cysteine.Kinetic investigation suggests the existence of several unstable intermediate complexes V(V)-cysteine whose rate of reduction may be considered to be the kinetic rate determining step.In particular, in an acidic medium, the similarity of their rate constants suggest that cystine or sulfinic acid are formed from the same transient species possessing 2 V(V) atoms for each ligand.In an ammonical medium, with an excess of the thioaminoacid, a red 1:1 complex V(V)-cystein readily appears.An investigation of this equilibrium has been carried out using stopped flow method.This reaction is followed by slower step involving electronic transfer again suggesting the existence of transient condensed compounds.
- Paumard, Jean-Paul,Cadiot, Michelle
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p. 441 - 447
(2007/10/02)
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- Kinetics of Chromic Acid Oxidation of Serine, Methionine and Cysteine
-
Oxidation of serine, methionine and cysteine was carried out in perchloric acid media by chromic acid.The reactions were found to be first order each in oxidant, reducing substrate and perchloric acid concentrations.Thus the rate of the reaction is given by the unified expression Added salts, viz., MnCl2, MnSO4, CoCl2, ZnSO4, generally retard the reaction rate with the exception of CoCl2 which accelerates the reaction rate.This accelerating effect is attributed to the electrophilic nature of the salt.Pyridine base has no effect on the reaction.Activation parameters were calculated in each case.Area/volume ratio has no effect on rates and thereby show the non-chair character of the reactions.Main reaction products were identified by preparing derivatives or chromatographically.Mechanisms proposed and rate expressions derived are consistent with the experimental results.Serine oxidation involves a rate determining hydride ion loss with a consequent production of electron deficient transition state which leads to a ready decarboxylation, whereas, methionine and cysteine oxidations involve the steps in which the attacks on sulphur atom are encountered, as sulphur is more nucleophilic than nitrogen.
- Goswami, K. B.,Chandra, G.,Srivastava, S. N.
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p. 252 - 258
(2007/10/02)
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- STUDIES ON PEPTIDES. XCVI. BEHAVIOR OF S-ACETAMIDOMETHYLCYSTEINE SULFOXIDE UNDER DEPROTECTING CONDITIONS IN PEPTIDE SYNTHESIS
-
The sulfoxide of Boc-Cys(S-acetamidomethyl)-OH was prepared by oxidation with sodium perborate.Mercuric acetate and iodine failed to cleave the S-protecting group from sulfoxide.Hydrogen fluoride and methanesulfonic acid partially converted the sulfoxide to S-p-methoxyphenylcysteine in the presence of anisole.A reducing reagent, thiophenol, converted the sulfoxide to acetamidomethyl phenyl sulfide and Nα-Boc-S-(phenylthio)cysteine.Keywords - S-acetamidomethylcysteine sulfoxide; mercuric acetate treatment; iodine treatment; hydrogen fluoride treatment; methanesulfonic acid treatment; thiophenol treatment
- Yajima, Haruaki,Akaji, Kenichi,Funakoshi, Susumu,Fujii, Nobutaka,Irie, Hiroshi
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p. 1942 - 1945
(2007/10/02)
-
