• Archives of Pharmacal Research
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• v.8 no.2
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• pp.77-84
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• 1985

[$^{2}$H$_{2}$] Tranylcypromine hydrochloride (trans-3, 3-dideuterio-2-phenylcyclopropylamine HCL) was synthesized for application to the metabolic studies. Mass fragmentation processes for the tranylcypromine and its two synthetic intermediates .gamma-phenyl-.gamma.-butyrolactone and trans-2-phenylcyclopropanecarboxylic acid were described based upon comparisons between labeled and unlabeled compounds.

• Journal of Microbiology and Biotechnology
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• v.16 no.1
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• pp.77-83
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• 2006

A gene encoding a $\gamma-butyrolactone$ autoregulator receptor was cloned from Saccharopolyspora erythraea, and the biochemical characteristics, including the autoregulator specificity, were determined with the purified recombinant protein. Using primers designed for the conserved amino acid sequence of Streptomyces $\gamma-butyrolactone$ autoregulator receptors, a 120 bp S. erythraea DNA fragment was obtained by PCR. Southern and colony hybridization with the 120 bp fragment as a probe allowed to select a genomic clone of S. erythraea, pESG, harboring a 3.2 kb SacI fragment. Nucleotide sequencing analysis revealed a 615 bp open reading frame (ORF), showing moderate homology (identity, $31-34\%$; similarity, $45-47\%$) with the $\gamma-butyrolactone$ autoregulator receptors from Streptomyces sp., and this ORF was named seaR (Saccharopolyspora erythraea autoregulator receptor). The seaR/pET-3d plasmid was constructed to overexpress the recombinant SeaR protein (rSeaR) in Escherichia coli, and the rSeaR protein was purified to homogeneity by DEAE-Sephacel column chromatography, followed by DEAE-ion-exchange HPLC. The molecular mass of the purified rSeaR protein was 52 kDa by HPLC gel-filtration chromatography and 27 kDa by SDS-polyacrylamide gel electrophoresis, indicating that the rSeaR protein is present as a dimer. A binding assay with tritium-labeled autoregulators revealed that rSeaR has clear binding activity with a VB-C-type autoregulator as the most effective ligand, demonstrating for the first time that the erythromycin producer S. erythraea possesses a gene for the $\gamma-butyrolactone$autoregulator receptor.

• Textile Coloration and Finishing
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• v.8 no.4
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• pp.19-24
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• 1996

Poly(3-hydroxybutylate) 및 그들 유도체의 화학적 합성을 위해 ${\gamma}$-butyrolactone(${\gamma}$BL)과 ${\gamma}$-valerolactone(${\gamma}$VL)을 사용 ${\gamma}$-butyrolactone($\beta$BL) 과의 개환중합을 시도했다. 공중합체는 5원황 락톤 단위를 포함한 코폴리에스테르를 $BF_{3}$. $OR_{t2}$ 촉매하에서 고상(bluk state)중합에 의해 얻었고, 이러한 방법으로 합성한 코폴리머의 구조를$^{1}H NMR$과 $^{13}C NMR$분석법으로 결정했다. 그결과 $\beta$BL, ${\gamma}$BL과 ${\gamma}$VL의 첨가비가 증가함에 따라 수율은 저하되었고, 또한 ${\gamma}$VL의 경우 4HV의 증가가 34~35%가 한계로써, ${\gamma}$VL의 첨가비가 0.5 (${\gamma}$VL/$\beta$VL=50/50)보다 증가 할지라도 안정상태를 유지하였다.

• Journal of Life Science
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• v.16 no.1
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• pp.76-81
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• 2006

A $\gamma-butyrolactone$ autoregulator receptor has a common activity as DNA-binding transcriptional repressors controlling secondary metabolism and/or morphological differentiation in Streptomyces. A gene (scaR) encoding it was cloned from Streptomyces cravuligerus, a clavulanic acid producer, and was in vitro characterized in a previous report. In this study to clarify the in vivo function of ScaR, a $\gamma-butyrolactone$ autoregulator receptor of Streptomyces clavuligerus, we constructed a scaR-deleted strain by means of homologous recombination. No difference in morphology was found between the wild-type strain and the scaR-disruptant, but the scaR-disruptant showed higher clavulanic acid production. This indicates that the ScaR in S. clavuligerus acts as a negative regulator of the biosynthesis of clavulanic acid, but plays no role in morphological differentiation.

• YAKHAK HOEJI
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• v.47 no.5
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• pp.331-338
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• 2003

A butyrolactone ester of cefazolin (CFZ-BTL) was synthesized by the esterification of cefazolin (CFZ) with $\alpha$-bromo-${\gamma}$-butyrolactone. The synthesis was confirmed by the spectroscopic analysis. The CFZ-BTL was more lipophilic than the CFZ when assessed by n-octanol/water partition coefficients at various pH. The CFZ-BTL itself did not show any antimicrobial activity in vitro, but after oral administration of CFZ-BTL to rabbits, exerted significant anti-microbial activity in serum samples when measured by the inhibion zone method in nutrient agar plates, due to conversion of CFZ-BTL to an active metabolite, probably CFZ, in the body. The CFZ-BTL was also converted into CFZ as confirmed by in vitro incubation study, with tissue homogenates (liver, blood and intestine) of rabbits. The liver showed the fastest conversion rate, probably via the hydrolysis mechanism. In vivo metabolism of CFZ-BTL to CFZ was also confirmed in vivo serum samples by HPLC. The oral bioavailability of CFZ-BTL in rabbits was 1.6-fold increased when compared to CFZ, resulting from followed by enhanced lipophilicity increased passive absorption in the intestine.

• Biotechnology and Bioprocess Engineering:BBE
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• v.10 no.6
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• pp.603-606
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• 2005

Ralstonia eutropha NCIMB 11599 and ATCC 17699 were grown, and their productions of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) [P(3HB-co-4HB)] compared. In flask cultures of R. eutropha NCIMB 11599, cell concentration, P(3HB-co-4HB) concentration and polymer content decreased considerably with increases in the ${\gamma}-butyrolactone$ concentration, and the 4HB fraction was also very low (maximum 1.74 mol%). In fed-batch cultures of R. eutropha NCIMB 11599, glucose and ${\gamma}-butyrolactone$ were fed as the carbon sources, under a phosphate limitation strategy. When glucose was fed as the sole carbon source, with its concentration controlled using an on-line glucose analyzer, 86% of the P(3HB) homopolymer was obtained from 201g/L of cells. In a two-stage fed-batch culture, where the cell concentration was increased to 104g/L, with glucose fed in the first step and constant feeding of ${\gamma}-butyrolactone$, at 6g/h, in the second, final cell concentration at 67h was 106g/L, with a polymer content of 82%, while the 4HB fraction was only 0.7mol%. When the same feeding strategy was applied to the fedbatch culture of R. eutropha ATCC 17699, where the cell concentration was increased to 42 g/L, by feeding fructose in the first step and ${\gamma}-butyrolactone$ (1.5g/h) in the second, the final cell concentration, polymer content and 4HB fraction at 74h were 51g/L, 35% and 32 mol%, respectively. In summary, R. eutropha ATCC 17699 was better than R. eutropha NCIMB 11599 in terms of P(3HB-co-4HB) production with various 4HB fractions.

• Applied Biological Chemistry
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• v.40 no.6
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• pp.593-596
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• 1997

In the course of search antagonistic fungi from soil in green house, four kind of fungi (AF1, AF2, AF3, AF4) were isolated, which have activities against Phytophthora capsici, Botrytis cinera, Rhizoctonia solani, Pythium ultimum and Fusarium oxysporum. The AF2 was identified according to the morphological description of Aspergillus terreus. This antagonistic fungus inhibiting various plant pathogens was effective to reduce disease incidence of cucumber seedlings caused by mixed inoculum of Rhizoctonia solani, Pythium ultimum and Fusarium oxysporum. Antifungal compound I was isolated and purified by fresh chromatography from A. terreus. The $^1H$ and $^{13}C$ assignment of compound I was achieved from two-dimensional $^1H-^1H\;COSY$, HMQC, HMBC with the add of homonuclear and heteronuclear double resonance experiment. The compound I was identified butyrolactone I (${\alpha}$-oxo-${\beta}$-(p-hydroxyphenyl)-${\gamma}$-(p-hydroxy-m-3,3-dimethyl-allylbenzyl)-${\gamma}$-methoxycarbonyl-${\gamma}$-butyrolactone, $C_{24}H_{24}O_7$, M.W.=424).

• Archives of Pharmacal Research
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• v.21 no.2
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• pp.164-167
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• 1998

Bis-${\gamma}$-lactones (1,2) having a perhydrofuro[3,4-c]furan-1,4-dione skeleton were designed as conformationally constrained diacylglycerol analogues. They were synthesized from D-apiose in 11 steps, and evaluated as $PKC-{\alpha}$ ligands by measuring their ability to displace bound $^3H$]PDBU from the enzyme. The compounds showed moderate binding affinities with $K_i$ values of 13.89 (${\pm}5.67$) ${\mu}M$ and 11.47 (${\pm}0.89$) ${\mu}M$, respectively. Their similar binding affinities indicate that these two bicyclic compounds were not effectively discriminated by $PKC-{\alpha}$ in terms of the direction of the side chain as other ligands built on similar bis-${\gamma}$-lactones.

• Microbiology and Biotechnology Letters
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• v.28 no.2
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• pp.71-79
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• 2000

Two typess of copolyesters, poly(3-hydroxybutyric acid-co-4-hydroxy-butyric acid)[P(3HB-co-4HB] and poly(3-hydroxybutyric acid-co-3-hydroxyvaleric acid)[P(3HB-co-3HV)], with various monomer ratios and different degree of microstructural heterogeneity were synthesized from Ralstonia eutropha H16 and Hydrogenophaga pseudoflava by using ${\gamma}$-butyrolactone and ${\gamma}$-valerolactone, respectively. The two bacteria showed a large difference in the utilization of ${\gamma}$-butyrolactone for cell growth and PHA synthesis. H. pseudoflava synthesized P(3HB-co-4HB) copolyesters with a wide range of 4HB content from 13 to 96 mol% depending on culture conditions, whiel R. eutropha H16 was able to synthesize the copolyesters containing less than 20 mol% of 4HB. An increase in the 4HB content in the P(3HB-co-4HB) copolyesters synthesized by H. pseud-oflava induced an lowering of their melting temperatures as well as their enthalpies of fusion. The increase in the 4HB content, however, increased the rate of degradation by an extracellular P(3HB) depolymerase. NMR spectros-copy and differential scanning calorimetry showed that the P(3HB-co-4HB) copolyesters from H. pseudoflava were generally microstructurally heterogeneous. The P(3HB-co-4HB) copolyesters) synthesized by R. eutropha H16 were rather random copolymers showing less microstructural heterogeneity than those synthesized by H. pseudoflava. The NMR D value analysis suggested that the monomer distribution of the P(3HB-co-3HV) copolymers from the two bacteria were relatively random.

• 한국생물공학회:학술대회논문집
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• 2003.10a
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• pp.11-11
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• 2003