• Journal of the Korean Chemical Society
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• v.39 no.2
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• pp.123-126
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• 1995

• Bulletin of the Korean Chemical Society
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• v.30 no.1
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• pp.163-171
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• 2009

Few $\alpha$-Hydroxy-$\beta$-amino acids were synthesized via various nucleophilic addition of the epoxide and followed by stereoselective nucleophilic substitution reaction and eliminative cleavage of the acetal selectively in diacetal compound. One of the synthesized $\alpha$-Hydroxy-$\beta$-amino acid reacted with L-leucine methylester to give corresponding dipeptide in good yields.

• Microbiology and Biotechnology Letters
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• v.1 no.1
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• pp.43-50
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• 1973

Thirty-three Mannich bases of 2,2'-methylene bis (3,4, 6-trichlorophenoxy-acetic acid) were synthesized hexachlorophene as potential antimicrobial agents and tested against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Trichophyton rubrum, Microsporum gypseum, Epidermophyton floccosum, Aspergillus niger and Aspergillus oryzae in vitro. It was found that: 1) 2,2'-Methylene bis [${\alpha}$-(3, 4, 6-trichlorophenoxy)-${\beta}$- (N,N -diethylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(N, N-dimethynlamo) propionoic acid] were active against Staphylococcus aureus and Bacillus subtilis at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively; 2) 2,2'-Methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3, 4, 6-trichlorophenoxy)-${\beta}$-(cyclohexylamino) propionic acid] were active against Trichophyton-rubrum at the concn. of 2 $\mu\textrm{g}$/$m\ell$ respectively; 3) 2,2'-Methylene bis [${\alpha}$-3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenyl-amino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trcihlorophenoxy)-${\beta}$-(piperidino) propionic acid] were active against Microsporum gypseum at the concn. of 2 $\mu\textrm{g}$/$m\ell$ respectively; 4) 2,2'-Methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxyphenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3, 4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxy phenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(o-chlorophenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(o-chloro-p-nitrophenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$- (3,4,6-trichlorophenoxy)-${\beta}$-(methylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(hydroxylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(cyclohexylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorphenoxy)-${\beta}$-(morpholino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(p-sulfophenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(4-sulfu-l-nayphthlamino) aoi!c rppioncd (were active against Epidermophyton floccosum at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively; 5) 2,2'-Methlene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxyphenylamino) propionic acid], 2,2'-methylene bis (a-(3,4,6-trichlorophenoxy)-${\beta}$-(m-hydroxy-p-carboxyphenylamino) propionic acid], 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(p-methylphenylamino) propionic acid] and 2,2'-methylene bis [${\alpha}$-(3,4,6-trichlorophenoxy)-${\beta}$-(hydroxylamino) propionic acid] were active against Aspergillus niger and Aspergillus oryzae at the concn. of 1 $\mu\textrm{g}$/$m\ell$ respectively.

• Natural Product Sciences
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• v.20 no.3
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• pp.160-169
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• 2014

44 compounds and 9 minerals were isolated from and detected in the New Zealand deer velvet antler Cervus elaphus var. scoticus L$\ddot{o}$nnberg. The chemical structures of (1 - 26) were identified on the basis of the spectroscopic methods and comparisons with literature, respectively. The structures were identified as cholesterol (CS, 6), 7-keto-CS (7), $7{\beta}$-hydroxy-CS (8), and $7{\alpha}$-hydroxy-CS (9), and included 12 steroid $3{\beta}$-O-(palmitic/stearic/myristic acid esters; PM/SA/MS) [CS-$3{\beta}$-O-PM (1 - 1), CS-$3{\beta}$-O-SA (1 - 2), CS-$3{\beta}$-O-MR (1 - 3), 7-keto-CS-$3{\beta}$-O-PM (2 - 1), 7-keto-CS-$3{\beta}$-O-SA (2 - 2), 7-keto-CS-$3{\beta}$-O-MR (2 - 3), $7{\beta}$-hydroxy-CS-$3{\beta}$-O-SA (3 -1), $7{\beta}$-hydroxy-CS-$3{\beta}$-O-PM (3 - 2), $7{\beta}$-hydroxy-CS-$3{\beta}$-O-MR (3 - 3), $7{\alpha}$-hydroxy-CS-$3{\beta}$-O-SA (4 - 1), $7{\alpha}$-hydroxy-CS-$3{\beta}$-O-PM (4 - 2), and $7{\alpha}$-hydroxy-CS-$3{\beta}$-O-MR (4 - 3)], dinonyl phthalate (5), 8 nucleic acids analogues [uracil (10), deoxyguanosine (11), deoxyuridine (12), uridine (13), deoxyadenosine (14), adenosine (15), inosine (16), and guanosine (17)], and the 9 free amino acids [L-phenylalanine (18), L-isoleucine (19), L-leucine (20), L-tyrosine (21), L-valine (22), L-proline (23), L-threonine (24), L-alanine (25), and L-hydroxyproline (26)]. Also, there are 8 kinds of amino acids [asparagine, serine, glutamine, glycine, histidine, arginine, methionine, and lysine], 2 sialic acids [N-acetylneuraminic acid (27), ketodeoxynonulosonic acid (28)], and 9 minerals [Na > K > Ca > Mg > Fe > Zn > B > Al > Cu] were detected from the autoaminoacid analyzer and ICP spectrometer, HPAEC-PAD/HPLC-FLD, respectively. 9 kinds of oxycholesterol-$3{\beta}$-O-fatty acid ester (2 - 1, 2 - 2, 2 - 3, 3 - 1, 3 - 2, 3 - 3, 4 - 1, 4 - 2, and 4 - 3) and 3 nucleic acids (12, 14, and 15) were isolated from the velvet antler for the first time. 6 kinds of steroids (7, 8, 9, 2 - 1, 3 - 1, and 4 - 1) were examined for their anti-proliferative effects against L1210, P388D1, K562, MEG-01, KG-1, MOLT-4, A549, HepG2, MCF-7, SK-OV-3, and SW-620 cancer cell lines. They showed anti-proliferative effects with $IC_{50}$ values of 0.06, 2.16, 2.42, > 50.0, 1.66 and $8.31{\mu}M$ against L1210, while the values were 24.05, 9.44, 5.22, 0.25. 9.48 and $49.77{\mu}M$ against P388D1, respectively. The others were inactive.

• Bulletin of the Korean Chemical Society
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• v.27 no.8
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• pp.1211-1218
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• 2006

The enantiomerically pure (2R,3S)- and (2R,3R)-3-amino-2-hydroxy-4-phenylbutanoic acids (AHPBA) 1 and 3 are readily obtained from D-glucono-a-lactone. Both AHPBAs are the structural key units of KMI derivatives which are the potent inhibitors of BACE 1 ($\beta$-secretase) and HIV protease. Additionally, the obtained AHPBAs 1 and 3 are converted to dipeptides of bestatin stereoisomers 2 and 4.

• Applied Chemistry for Engineering
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• v.26 no.1
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• pp.111-115
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• 2015

Two new analogs of bestatin were prepared from $\small{D}$-leucine and $\small{D}$-valine in a stereoselective and efficient way. An aminopeptidase inhibitor bestatin shows significant biological effects on immunomodulation and is marketed for the treatment of acute myelocytic leukemia. The key intermediates, trans-oxazolidine methyl esters 2a and 2b, were obtained with more than 20 to 1 stereoselectivity in a one-pot procedure by the three cascade reactions between N-hydroxymethyl protected ${\alpha}$-amino aldehydes (4a and 4b) and phenylsulfonylnitromethane ($PhSO_2CH_2NO_2$) and the following in-situ ozonolysis. Basic hydrolysis of 2a and 2b, and then the peptide coupling with $\small{L}$-Leu-OMe produced the protected derivatives of two new bestatin analogs, 3a and 3b, respectively. The new isobutyl and isopropyl analogs of bestatin (1a and 1b) were produced in overall 51% and 38% yields, respectively, with high stereoselectivity from the corresponding protected ${\alpha}$-amino aldehydes 4 in a six-step process.

• Proceedings of the Korean Society of Crop Science Conference
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• 2017.06a
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• pp.36-36
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• 2017

Out of twenty common protein amino acids, there are many kinds of non protein amino acids (NPAAs) that exist as secondary metabolites and exert ecological functions in plants. Mimosine (Mim), one of those NPAAs derived from L. leucocephala acts as an iron chelator and reversely block mammalian cell cycle at G1/S phases. Cysteine (Cys) is decisive for protein and glutathione that acts as an indispensable sulfur grantor for methionine and many other sulfur-containing secondary products. Cys biosynthesis includes consecutive two steps using two enzymes-serine acetyl transferase (SAT) and O-acetylserine (thiol)lyase (OASTL) and appeared in plant cytosol, chloroplast, and mitochondria. In the first step, the acetylation of the ${\beta}$-hydroxyl of L-serine by acetyl-CoA in the existence of SAT and finally, OASTL triggers ${\alpha}$, ${\beta}$-elimination of acetate from OAS and bind $H_2S$ to catalyze the synthesis of Cys. Mimosine synthase, one of the isozymes of the OASTLs, is able to synthesize Mim with 3-hydroxy-4-pyridone (3H4P) instead of $H_2S$ for Cys in the last step. Thus, the aim of this study was to clone and characterize the cytosolic (Cy) OASTL gene from L. leucocephala, express the recombinant OASTL in Escherichia coli, purify it, do enzyme kinetic analysis, perform docking dynamics simulation analysis between the receptor and the ligands and compare its performance between Cys and Mim synthesis. Cy-OASTL was obtained through both directional degenerate primers corresponding to conserved amino acid region among plant Cys synthase family and the purified protein was 34.3KDa. After cleaving the GST-tag, Cy-OASTL was observed to form mimosine with 3H4P and OAS. The optimum Cys and Mim reaction pH and temperature were 7.5 and $40^{\circ}C$, and 8.0 and $35^{\circ}C$ respectively. Michaelis constant (Km) values of OAS from Cys were higher than the OAS from Mim. Inter fragment interaction energy (IFIE) of substrate OAS-Cy-OASTL complex model showed that Lys, Thr81, Thr77 and Gln150 demonstrated higher attraction force for Cys but 3H4P-mimosine synthase-OAS intermediate complex showed that Gly230, Tyr227, Ala231, Gly228 and Gly232 might provide higher attraction energy for the Mim. It may be concluded that Cy-OASTL demonstrates a dual role in biosynthesis both Cys and Mim and extending the knowledge on the biochemical regulatory mechanism of mimosine and cysteine.

• Journal of Animal Science and Technology
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• v.63 no.6
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• pp.1386-1396
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• 2021

Copper is an essential mineral for pigs, thus it is used as a feed additive in the forms of copper sulfate. Therefore, this study aimed at characterizing the fecal microbiota shifts in pigs as fed by different forms of copper supplementation. 40 growing pigs aged 73 ± 1 days with an average weight of 30.22 ± 1.92kg were randomly divided into 5 groups. The control group (CON) fed with basal diet, while treatment groups were fed a basal diet supplemented with 100 ppm/kg of copper sulfate (CuSO₄), Cu-glycine complex (CuGly), Cu-amino acid complex (CuAA), and Cu-hydroxy(4methylthio)butanoate chelate complex (CuHMB) for 28 days of trial, respectively. The data presented the comparison between inorganic and organic copper supplementation through gut microbiota in growing pigs. Alpha and Beta diversity anaylsis resulted in copper supplementation did shifted gut microbioal community structure. At the phylum level, Firmicutes and Bacteroidetes were the most abundant phyla at all times regardless of treatment. At the genus level, the relative abundances of Prevotella, Lactobacillus, Megasphaera, and SMB53 of the CuGly and CuHMB groups were significantly higher than those of copper sulfate and basal diet groups. Overall, this study may provide the potential role of organic copper replacing inorganic copper, resulting in increased beneficial bacteria in the pig gut.