• Applied Chemistry for Engineering
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• v.31 no.2
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• pp.187-192
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• 2020

(2S,3R)-3-hydroxyhomoserine lactone (HSL) has been used as a key intermediate for the synthesis of various biologically active compounds. In this study, we demonstrated an efficient synthesis of HSL via anti selective dihydroxylation of a protected vinyl glycine analog with an oxabicyclo[2.2.2]octyl orthoester (OBO) ester group. Because the acyclic conformation of the substrate was efficiently controlled by the bulky OBO ester group, a diastereoselectivity of > 10 : 1 was obtained in the dihydroxylation reaction without the use of a chiral reagent. By using this result, the target compound 1 can be obtained from commercially available N-Cbz-L-serine 2 in seven steps with an overall yeid of 34%. This result could be applied to the stereoselective synthesis of biologically active molecules containing a vicinal amino diol moiety.

• Journal of Nutrition and Health
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• v.4 no.4
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• pp.39-46
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• 1971

Since ${\beta}-aminoethylphosphonic$ acid was discovered in the living organism, the biosynthesis and biological function of aminophosphonic acids have been extensively studied. The purpose of this project consists in the two parts: 1)the preparation of DL-1-amino-2-phenylethylphosphonic acid (Phenylalanine aminophosphonic acid) and DL-1-amino-3-methylbutyl-phosphonic acid (Isoleucine aminophosphonic acid) by the method of Chamber and Isbell. 2) the study of metabolism and biological functions of those synthetic materials by the animal experiment (white rats) The importance of this project proved to be the first experience fed by animals for the elucidation of biochemical and metabolic functions in the animal body. The following organic synthesis of DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenylethylphosphonic acid are studied. 1)Synthesis of DL-1-amino-3-methylbutylphosphonic acid a) Synthesis of Iso-butylbromide b) Synthesis of Ethyl iso-butylmalonate c) Synthesis of Iso-caproic acid d) Synthesis of $Ethyl-{\alpha}-bromo$ iso-caproate e) Synthesis of $Triethyl-{\alpha}-phosphono$ iso-caproate f) Synthesis of DL-1-amino-3-methylbutylphosphonic acid 2)Synthesis of DL-1-amino-2-phenylethylphosphonic acid a) Synthesis of Diethyl phosphite b) Synthesis of Ethylchloro acetate c) Synthesis of Triethyl phospho acetate d) Synthesis of Triethyl benzyl phospho acetate e) Synthesis of DL-1-amino-2-phenylethylphosphonic acid The synthetic compounds; DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenyl ethylphosphonic acid which are essential amino acid (isoleucine, phenylalanine)analogue are supplemented to the animal diet at the level of 0.2% and 0.4% for isoleucine analogue and 0.35% and 0.7% for phenylalanine analogue. The plain isoleucine and phenylalanine at the same level in the diet are fercilitated as comparable groups in this study. Two sets of experience including 100 male rats were carried out for seven weeks each total 14 weeks. During this period, urine samples, and each big organs were collected for the analysis of total nitrogen, phosphorus, and glycogen contents in the individual samples by Micro Kjeldahl Fisk & Subbarow and Nelson Somogye, method. 1) The result of the project a) The yield of DL-1-amino-3-methylbutylphosphonic acid and DL-1-amino-2-phenylethylphosphonic acid showed low tendency at the level of 12.5% and 20% Melting point of those two compounds were very high and the ${\alpha}-amino$ group in the synthetic compounds showed positive reaction with ninhydrin in the violet color. b) Ail the experimental groups included in this study revealed statistically no significant difference in the organ weight, total body nitrogen retention and urinary phosphorus excretion This means isoleucine aminophosphonic acid and Phenylalanine aminophosphonic acid were utilized in the body as much as the plain amino acids, isoleucine and phenylalanine did. c) The glycogen contents in the liver of the phenylalaine aminophosphonic acid gruop showed higher statistically significant(p<0.05) in the comparision with the group of the Phenylalanine and the Standard-2. It was noteworthy that the higher glycogen content in the liver might indicate the significance in the incorporation of phenylalanine aminophosphonic acid into the intermediate of tricarboxylic acid cycle as activated state.

• Biomedical Science Letters
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• v.15 no.2
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• pp.105-112
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• 2009

The screening of the anti-cancer activity of the chemical library provided 2-thio-4-aminopyrimidine as the initial hit. The confirmation of structure and biological effect of hit was performed by synthesis and biological evaluation. The optimization of hit was performed by derivatization of substituents while keeping the core structure. The evaluation of growth inhibitory activity was carried out using SRB assay against 6 human cancer cell lines and human fibroblast. The growth inhibitory activity of compounds showed substituent dependency and more than 5 compounds showed complete growth inhibition of cancer cell lines at 10 ${\mu}M$ concentration. Chemical library screening followed by synthetic modification provided possibility that 2-thio-4-aminopyrimidine can be used as a new scaffold for the development of anti-cancer agent.

• Journal of Microbiology and Biotechnology
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• v.13 no.6
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• pp.833-840
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• 2003

Sperm motility of salmonid fishes is suppressed by external $K^{+}$ and initiated by decrease of $K^{+}$ concentration surrounding the sperm. It was shown that the decrease in external $K^{+}$ concentration induced not only the initiation of sperm motility, but also hyperpolarization of the plasma membrane and synthesis of cAMP in the sperm of rainbow trout, steelhead trout, and masu salmon. Inhibitors of $K^{+}$ channels, especially voltage-dependent $K^{+}$ channels, inhibited these three reactions, and the inhibitions were abolished by subsequent addition of a $K^{+}$ ionophore, valinomycin, suggesting that $K^{+}$ efflux through the $K^{+}$ channel contributes to rapid changes in the membrane potential of sperm and cAMP synthesis, thereby resulting in the initiation of sperm motility of salmonid fishes.

• Applied Biological Chemistry
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• v.31 no.4
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• pp.371-375
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• 1988

Streptomycetes are attractive microorganisms for their production of various secondary metabolites such as antibiotics. Now, the development of gene manipulation in this microorganisms enables the cloning and analysis of the genes which coding for antibiotic biosynthesis and resistance to the drug. In this article, we reviewed the studies with respect to the mechanisms of self-protection and cloning of the genes cloning for antibiotic biosynthesis, particularly, in microorganisms which produce antibiotic inhibitors of protein synthesis.

• Bulletin of the Korean Chemical Society
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• v.29 no.10
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• pp.1946-1950
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• 2008

The synthesis of new 5-cyano-1,1-disubstituted phthalans having aromatic and aminoalkyl groups at C-1 position of phthalan ring and their biological evaluation are described. Most compounds exhibited comparable ejaculation-retarding effects to citalopram. Of these compounds, 3a, e showed excellent efficacy in delaying ejaculation.

• Bulletin of the Korean Chemical Society
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• v.31 no.9
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• pp.2467-2472
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• 2010

Twenty novel tetramic acid derivatives (E)-3-(1-(alkyloxyamino)ethylidene)-1-alkylpyrrolidine-2,4-diones were synthesized by the reaction of 3-(1-hydroxyethylidene)pyrrolidine-2,4-diones with O-alkyl hydroxylamines. The title compounds were confirmed by IR, $^1H$ NMR, MS and elemental analysis. The structure of compound 6r was further verified by X-ray diffraction crystallography. The bioassays showed that most of the title compounds exhibited noticeable herbicidal and fungicidal activities.

• Journal of the Korean Chemical Society
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• v.57 no.4
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• pp.455-460
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• 2013

A novel and simple method for the synthesis of 2-amino-4H-pyran-3,4,5-tricarboxylate derivative and the evaluation of their antibacterial activity against Pseudomonas syringae, Xanthomonas citi and Pectobacterium carotovorum are reported. The structure of the isolated compounds has been determined by means of $^1H/^{13}C$ NMR and FT-IR Spectroscopy. The reaction of alkyl isocyanides with acetylenic esters in the presence of dimethyl acetone-1,3-dicarboxylate in the present of $BF_3.SiO_2$ at ambient temperature. Some of the compound showed significant inhibition to growth of bacteria.

• Journal of Applied Biological Chemistry
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• v.43 no.2
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• pp.101-103
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• 2000

The synthesis and resolution of ($\pm$)-10,11-dihydroxydibenzosuberenone 3, a potential pharmaceutical compound, is described. It was synthesized from the 5H-dibenzo[a,d]cycloheptene-5-one (dibenzosuberenone) 1, and converted to diastereomeric isomers using (R)-(+)-$\alpha$-methylbenzylamine. Optical resolution of ($\pm$)-10,11-dihydroxydibenzosuberenone 3 was possible by fractional recrystallization of the diastereomer formed in ethanol. The optical resolution of 10,11-dihydroxydibenzosuberenone through formation of its phosphoamidates 5 using the (R)-(+)-$\alpha$-methylbenzylamine was achieved. These compounds provided the optical rotation of [${\alpha}]=-64.3$ for (-)-10,11-dihydroxy-dibenzosuberenone and [${\alpha}]=+61.3$ for (+)-10,11-dihydroxydibenzosuberenone. The (-)- and (+)-enantiomers were prepared in five steps from dibenzosuberenone with overall yields of 11.66% and 9.38%, respectively.

• Applied Biological Chemistry
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• v.40 no.6
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• pp.588-592
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• 1997

The new type ligand, bisphosphonites, were easily prepared through ligand exchange reaction of bis (diethylamino)phosphine with diols. These bisphosphonites reacted with $(COD)^2Rh^+BF_4\;^-$ to corresponding bisphosphonite-rhodium(I) comlexes, of which X-ray crystallography was for the first time investigated. This organometallic compound was applicated in hydroformylation reaction as catalyst, and proved to be very effective one.