• 제목/요약/키워드: Decarboxylation

검색결과 89건 처리시간 0.02초

하고초의 생리활성 성분 Triterpenic Acids의 FAB-MS를 이용한 구조 규명 (Structural determination of triterpenic acids in Prunellae Spica by fast atom bombardment tandem mass spectrometry)

  • 안영민;이강노;홍종기
    • 분석과학
    • /
    • 제21권4호
    • /
    • pp.245-258
    • /
    • 2008
  • 본 연구에서는 하고초의 지표성분인 triterpenic acids 5종을 컬럼 크로마토그래피와 역상 HPLC를 이용하여 추출 및 분리했고, 이들 성분의 순도는 90% 이상임을 HPLC를 이용하여 확인했다. 고속원자충돌 이온화법-고분해능 질량분석기(FAB-HRMS)를 사용하여 지표성분의 분자량 및 원소조성을 결정했으며, 지표성분의 구조 분석은 FAB-MS/MS 의해 음이온 및 양이온 모드에서 수행하였다. Triterpenic acid류의 충돌유발분해(collision-induced dissociation, CID) 탄뎀질량분석(MS/MS) 스펙트럼에서 protonated molecule인 $[M+H]^+$ 및 deprotonated molecule인 $[M-H]^-$ 이온의 CID는 주로 retro Diels-Alder (RDA), 탈수 (dehydration) 및 탈탄산(decarboxylation) 반응에 의한 다양한 생성이온들이 나타났다. 특히, $[M-H]^-$이온의 CID-MS/MS 스펙트럼에서는 charge-remote fragmentation (CRF) 현상에 의한 이온들도 특성이온으로 나타났다. 이들 CID-MS/MS 스펙트럼의 해석을 통하여 하고초의 지표성분인 triterpenic acids의 구조 규명을 수행하였다.

Synthesis of 2,2'-Dipyrryl Ketones from Pyrrole-2-carboxylic Acids with Trifluoroacetic Anhydride

  • Kim, Se Hee;Lim, Jin Woo;Yu, Jin;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
    • /
    • 제34권9호
    • /
    • pp.2604-2608
    • /
    • 2013
  • An efficient synthesis of 2,2'-dipyrryl ketones has been carried out from pyrrole-2-carboxylic acids using trifluoroacetic anhydride (TFAA). Simultaneous generation of both mixed anhydride and 2-unsubstituted pyrrole, via facile decarboxylation with in-situ generated TFA, made their cross reaction (intermolecular Friedel-Crafts acylation) possible and efficient.

$(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)acetic acid 합성과 분할 (Synthesis of $(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)Acetic Acid and its Resolution)

  • 권순경
    • 약학회지
    • /
    • 제39권4호
    • /
    • pp.433-437
    • /
    • 1995
  • Optically pure(-)-and (+)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acids were prepared. The racemate was synthesized through three steps. By condensation of p-cnorobiphenyl with diethyl ketomalonate in the presence of SnCl$_{4}$, diethyl $\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)malonate (1) was formed and subsequently ($\pm$)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acid (3) was obtained through hydrolysis and decarboxylation. For the separation of the racemate the classical resolution method, derivatization of a racemate by reaction with an optically pure compound was employed. In this case the optically pure compound were [R]-(+)-$\alpha$-methylbenzylamine and [S]-(-)-$\alpha$-methylbenzylamine. Diastereomeric salts between acids and bases could be easily separated by crystallization in absolute ethanol.

  • PDF

Bioconversion of Gamma-Aminobutyric Acid from Monosodium Glutamate by Lactobacillus brevis Bmb5

  • Jeong, Anna;Yong, Cheng Chung;Oh, Sejong
    • Journal of Microbiology and Biotechnology
    • /
    • 제29권11호
    • /
    • pp.1745-1748
    • /
    • 2019
  • Gamma-aminobutyric acid (GABA) plays important roles in host physiology. However, the effects of GABA are greatly restricted due to its low bioavailability in the human body. Here, a high acid-tolerance GABA-producing strain, Lactobacillus brevis Bmb5, was isolated from kimchi. Bmb5 converted glutamate to GABA (7.23 ± 0.68 ㎍/μl) at a rate of 72.3%. The expression of gadB gene, encoding the enzyme involved in the decarboxylation of glutamate to GABA, was decreased upon incubation. Our findings indicate GABA production in Bmb5 is not directly correlated with gadB gene expression, providing new insight into the mechanisms underlying GABA production in Lactobacillus.

Modulation of Branched-Chain Amino Acid Metaolism by Exercise in Rats

  • Kim, Hyun-Sook
    • Journal of Nutrition and Health
    • /
    • 제27권9호
    • /
    • pp.892-900
    • /
    • 1994
  • A variety of important roles for branched-chain amino acids in metabolic regulation has been suggested. Branched-chain $\alpha$-keto acid dehydrogenase(BCKAD) complex is a rate limiting enzyme in branched-chain amino acid metabolism. The purpose of this study was to examine the effects of exercise on the activity and activity state of branched-chain $\alpha$-keto acid dehydrogenase in rat hert and liver thssues. Forty-eight Sprague-Dawley rats were assigned into three experimental groups : sedentary control, exercised, or exercised-rested. Submaximal exercise(running) for two hours significantly increased basal activity without a change in total activity in both tissues, with a concomitiant increase in activity state of the enzyme complex. At 10 min post-exercise, heart enzyme activity significantly decreased, though not to the control level, while liver enzyme activity remained unchanged. These data suggested that the exercise-induced increase in branched-chain $\alpha$-keto acid decarboxylation in rat tissues may not be the result of enzyme synthesis, but rather is due to increased activity of the BCKAD.

  • PDF

Determination of Branched-Chain α-Keto Acid Dehydrogenase Activity in Rat Tissues

  • Kim, Hyun-Sook;Johnson, Wayne A.
    • BMB Reports
    • /
    • 제28권1호
    • /
    • pp.12-16
    • /
    • 1995
  • The branched-chain ${\alpha}$-keto acid dehydrogenase (BCKAD) complex is a rate limiting enzyme which catalyzes the oxidative decarboxylation of branched-chain ${\alpha}$-keto acids. Numerous studies have suggested that BCKAD is subject to covalent modification in vitro via phosphorylation and dephosphorylation, which are catalyzed by a specific kinase and phosphatase, respectively. The biggest difficulty in the assay of BCKAD activity is to arrest the interconversion between the active and inactive forms. BCKAD activity was determined from fresh rat heart and liver tissues using homogenizing and assay buffers containing inhibitors of phosphatase and kinase. The results suggest that a radiochemical assay using ${\alpha}$-keto[1-$^{14}C$]-isovalerate as a substrate for the enzyme can be applied as a reliable method to determine in vitro enzyme activity with arrested interconversion between the active and inactive forms of the BCKAD complex.

  • PDF

Single Electron Transfer Promoted Photocyclization Reactions of ($\omega$-Phthalimidoalkylthio) acetic Acids

  • Yoon, Ung-Chan;Lee, Sang-Jin;Oh, Sun-Wha;Cho, Dae-Won
    • Journal of Photoscience
    • /
    • 제8권3_4호
    • /
    • pp.99-104
    • /
    • 2001
  • Studies have been conducted to explore single electron transfer (SET) promoted photocyclization reactions of ($\omega$-phthalimidoalkylthio)acetic acids (alkyl=ethyl, n-propyl, n-butyl, n -hexyl and n-nonyl). Photocyclizations occur in methanol in modest yields to produce cyclized products in which phthalimide carbonyl carbon is bonded to the carbon of side chain in place of the carboxylic group. The initially formed cyclized products undergo efficient water eliminations to produce enthiol ethers in secondary ground state reactions.

  • PDF

GABA의 효능과 이용 (Effects and Utilization of GABA)

  • 임상동;김기성
    • Journal of Dairy Science and Biotechnology
    • /
    • 제27권1호
    • /
    • pp.45-51
    • /
    • 2009
  • $\gamma$-aminobutyric acid (GABA) is a ubiquitous nonprotein amino acid that is produced primarily by $\alpha$-decarboxylation of L-glutamic acid (Glu) catalyzed by the enzyme glutamate decarboxylase (GAD). It is well known as a neurotransmitter that regulates inhibitory neurotransmission in the mammalian central nervous system. In addition, GABA has been proved to be effective for lowering blood pressure in mammals. This paper is intended to provide basic information about GABA, including the functional and biological activity of GABA, GABA production by lactic acid bacteria, and the utilization of GABA in the production of dairy products.

  • PDF

Identification of Amino Acid Residues in the Carboxyl Terminus Required for Malonate-Responsive Transcriptional Regulation of MatR in Rhizobium leguminosarum bv. trifolii

  • Lee, Hwan-Young;Kim, Yu-Sam
    • BMB Reports
    • /
    • 제34권4호
    • /
    • pp.305-309
    • /
    • 2001
  • MatR in Rhizobium trifolii is a malonate-responsive transcription factor that regulates the expression of genes, matABC, enabling decarboxylation of malonyl-CoA into acetyl-CoA, synthesis of malonyl-CoA from malonate and CoA, and malonate transport. According to an analysis of the amino acid sequence homology, MatR belongs to the GntR family The proteins of this family have two-domain folds, the N-terminal helix-turn-helix DNA-binding domain and the C-terminal ligand-binding domain. In order to End the malonate binding site and amino acid residues that interact with RNA polymerase, a site-directed mutagenesis was performed. Analysis of the mutant MatR suggests that Arg-160 might be involved in malonate binding, whereas Arg-102 and Arg-174 are critical for the repression activity by interacting with RNA polymerase.

  • PDF

노르디테르펜 알칼로이드류의 산화적 특성 (Oxidative Characteristics of Norditerpene Alkaloids)

  • 송인성;김혜경;허경희;이정규
    • 생약학회지
    • /
    • 제37권1호통권144호
    • /
    • pp.60-66
    • /
    • 2006
  • Norditerpene alkaloids are the main toxic principles of traditional oriental herb 'chuawu(bu-shi),' which have been used in Chinese materia medica mainly for the treatment of musculoskeletal disorders. They are biosynthesized via cyclization of geranylgeranyl pyrophosphate, incoration of 2-aminoethanol and decarboxylation not via amino acid pathway, and the structural characteristics have tempted several oxidative reactions. In this study various norditerpene alkaloids were subjected to react active manganese dioxide and oxoammonium salt as oxidants. The oxidation was proceeded as dealkylation with aconitine type and dehydrogenations with lycoctonin and heteratisine type.