• 제목/요약/키워드: chiral analysis

검색결과 88건 처리시간 0.023초

Development of Saccharomyces cerevisiae Reductase YOL151W Mutants Suitable for Chiral Alcohol Synthesis Using an NADH Cofactor Regeneration System

  • Yoon, Shin Ah;Jung, Jihye;Park, Seongsoon;Kim, Hyung Kwoun
    • Journal of Microbiology and Biotechnology
    • /
    • 제23권2호
    • /
    • pp.218-224
    • /
    • 2013
  • The aldo-keto reductases catalyze reduction reactions using various aliphatic and aromatic aldehydes/ketones. Most reductases require NADPH exclusively as their cofactors. However, NADPH is much more expensive and unstable than NADH. In this study, we attempted to change the five amino acid residues that interact with the 2'-phosphate group of the adenosine ribose of NADPH. These residues were selected based on a docking model of the YOL151W reductase and were substituted with other amino acids to develop NADH-utilizing enzymes. Ten mutants were constructed by site-directed mutagenesis and expressed in Escherichia coli. Among them, four mutants showed higher reductase activities than wild-type when using the NADH cofactor. Analysis of the kinetic parameters for the wild type and mutants indicated that the $k_{cat}/K_{m}$ value of the Asn9Glu mutant toward NADH increased 3-fold. A docking model was used to show that the carboxyl group of Glu 9 of the mutant formed an additional hydrogen bond with the 2'-hydroxyl group of adenosine ribose. The Asn9Glu mutant was able to produce (R)-ethyl-4-chloro-3-hydroxyl butanoate rapidly when using the NADH regeneration system.

Dimesogenic Compounds with Chiral Tails: Synthesis and Liquid Crystalline Properties of a Homologous Series of a, w-Bis[4-(4'-(S)-( -)-2-methylbutoxycarbonylbiphenyl- 4-oxycarbonyl)phenoxy]alkanes

  • 최이준;최봉구;김재훈;진정일
    • Bulletin of the Korean Chemical Society
    • /
    • 제21권1호
    • /
    • pp.110-117
    • /
    • 2000
  • A series of new liquid crystalline dimesogenic compounds with chiral tails was synthesized, and their thermal and liquid crystalline properties were studied. The chain length of the central polymethylene spacers (x) was varied from dimethylene (2) to decamethylene (12). These compounds were characterized by elemental analysis, IR and NMR spectroscopy, differential scanning calorimetry (DSC), and cross-polarizing microscopy. All compounds were found to be enantiotropically liquid crystalline, and the values of melting ($T_m$) and isotropization temperature ($T_i$) as well as enthalpy change (Δ$H_i$) and entropy change for isotropization (Δ$S_i$) decreased in a zig-zag fashion revealing the so-called odd-even effect as x increases. Their mesomorphic properties fall into three categories depending upon x; (a) compounds with x=2 and 4 formed two different mesophases, smectic and cholesteric phases in that order on heating, and vice versa on cooling, (b) compounds with x=3, 7, 8, 10 and 11 reversibly formed only the cholesteric phase, and (c) compounds with x=5, 6, 9 and 12 exhibited only a cholesteric phase on heating, whereas on cooling they formed two different mesophases, cholesteric and smectic phases, sequentially.

Free vibration analysis of chiral double-walled carbon nanotube using non-local elasticity theory

  • Rakrak, Kaddour;Zidour, Mohamed;Heireche, Houari;Bousahla, Abdelmoumen Anis;Chemi, Awda
    • Advances in nano research
    • /
    • 제4권1호
    • /
    • pp.31-44
    • /
    • 2016
  • This article is concerned with the free vibration problem for chiral double-walled carbon nanotube (DWCNTs) modelled using the non-local elasticity theory and Euler Bernoulli beam model. According to the governing equations of non-local Euler Bernoulli beam theory and the boundary conditions, the analytical solution is derived and two branches of transverse wave propagating are obtained. The numerical results obtained provide better representations of the vibration behaviour of double-walled carbon nanotube, where the aspect ratio of the (DWCNTs), the vibrational mode number, the small-scale coefficient and chirality of double-walled carbon nanotube on the frequency ratio (${\chi}^N$) of the (DWCNTs) are significant. In this work, the numerical results obtained can be used to predict and prevent the phenomenon of resonance for the forced vibration analyses of double -walled carbon nanotubes.

Burkholderia cepacia Strain G4 (pHG-2) Accumulates cis-3-Methyl-3,5-cyclohexadien-1,2-diol While Growing on Toluene

  • Hur, Hor-Gil
    • Journal of Applied Biological Chemistry
    • /
    • 제43권1호
    • /
    • pp.44-48
    • /
    • 2000
  • Burkholderia cepacia strain G4 (pHG-2) containing toluene 2-monooxygenase and toluene dioxygenase, was able to grow on toluene and accumulate cis-3-methyl-3,5-cyclohexadien-1,2-diol (cis-toluene dihydrodiol) in the liquid culture. The cis-toluene dihydrodiol produced was identical to the authentic compound, as judged through mass spectrometry and nuclear magnetic resonance analysis. Our results indicate that pHG-2 provides an economical means to produce chemically-important chiral synthons while growing on toluene.

  • PDF

건생강에 함유된 키랄성 향기성분의 이성질체 조성 분석 (Analysis of Enantiomeric Composition of Chiral Flavor Components from Dried Ginger (Zingiber afficinale Roscoe))

  • 서혜영;노기미;심성례;류근영;한규재;라젠드라 게왈리;김경수
    • 한국식품영양과학회지
    • /
    • 제35권7호
    • /
    • pp.874-880
    • /
    • 2006
  • 건생강 제품의 진위판별을 위한 기초자료를 제공하기 위하여 건조된 생강으로부터 휘발성 향기성분을 추출하여 향기특성을 분석하고, MDGC/MS에 의해 키랄성 휘발성분의 enantiomeric composition을 분석하였다. 건생강에서 총 57종을 동정하였으며 주요 휘발성 향기성분은 zingiberene, ${\beta}-sesquiphellandrene$, ${\beta}-bisabolene$, (E,E)-${\alpha}-farnesene$${\alpha}-curcumene$이었다. 건생강에 함유된 키랄성 향기성분 중에서 enaniomeric composition을 측정하기 위해 선택된 키랄화합물 중 ${\alpha}-pinene$ 및 nerolidol은 높은 enantiomeric purity(>96%)로 검출되었으며, ${\beta}-pinene$은 (R)-enantiomer만이 검출되어 특이적이었다. ${\alpha}-Terpineol$은 (R)-enantiomer가 72%로 높게 나타났으며 linalool과 4-terpineol은 두 이성질체가 혼합된 것으로 나타났다. Limonene의 enantiomeric excess(ee, %)는 17.2%로 (S)-enantiomer가 주요 이성질체이었다. 따라서 이러한 키랄성 향기성분의 enantiomeric composition은 건생강의 진위평가를 위한 변수로 사용될 수 있을 것으로 생각된다.

Gamakamide-E, a Strongly Bitter Tasting Cyclic Peptide with a Hydantoin Structure from Cultured Oysters Crassostrea gigas

  • Lee, Jong-Soo;Satake, Masayuki;Horigome, Yoichi;Oshima, Yasukatsu;Yasumoto, Takeshi
    • Fisheries and Aquatic Sciences
    • /
    • 제15권1호
    • /
    • pp.15-19
    • /
    • 2012
  • A new cyclic peptide (six-membered amino acid), gamakamide-E (L-Leu-L-Met (SO)-L-Me-Phe-L-Leu-D-Lys-L-Phe), was isolated as a strongly bitter tasting compound from cultured oysters, Crassostrea gigas. The molecular formula of $C_{43}H_{61}N_7O_8S$ was deduced from high resolution fast atom bombardment mass spectrometry (HR FAB-MS) ($[M+H]^+$ m/z 836.4356 ${\Delta}$= -2.4 mmu). Its unique structure including a hydantoin structure was firstly elucidated by nuclear magnetic resonance (NMR) analysis. Stereochemistries of constituent amino acids were determined by chiral high performanced liquid chromatography analysis of natural and synthesized peptides.

Four New Furanosesquiterpenes Isolated from the Marine Sponge Dysidea species

  • Yeong Du Yoo;Jung-Rae Rho
    • 한국자기공명학회논문지
    • /
    • 제27권4호
    • /
    • pp.35-41
    • /
    • 2023
  • From a marine sponge Dysidea species, four new furanosesquiterterpenoids were isolated and characterized. Their structural elucidation was achieved through an extensive analysis employing NMR, MS data, and DFT method. Notably, all compounds shared as identical molecular formula. Compound 2 was identified as a derivative of compound 1, while compounds 3 and 4 exhibited an identical planar structure. Determination of the configurations of chiral centers in compounds 1 and 2 involved a comparative analysis between measured and calculated ECD spectra, along with the application of DP4+ probability analysis. Distinctly, the configurations of isomers 3 and 4 were established by scrutinizing proton chemical shifts based on the NOE correlation.

Response of orthotropic Kelvin modeling for single-walled carbon nanotubes: Frequency analysis

  • Hussain, Muzamal;Naeem, Muhammad N.;Tounsi, Abdelouahed
    • Advances in nano research
    • /
    • 제8권3호
    • /
    • pp.229-244
    • /
    • 2020
  • In this paper, modified Kelvin's model has been used to analyze the orthotropic vibration frequencies of single walled carbon nanotubes with clamped-clamped and clamped-free boundary conditions. For this system the governing equation is developed with wave propagation approach. Armchair, zigzag and chiral structures are considered for the vibrational analysis to investigate the effect of different modes, in-plane rigidity and mass density per unit lateral area. Throughout the computations, on decreasing the length-to-diameter ratios, the frequencies of said structure increases. In addition, by increasing three different value of in-plane rigidity resulting frequencies also increase and frequencies decrease on increasing mass density per unit lateral area. The results generated using computer software MATLAB to furnish the evidence regarding applicability of present model and also verified by available published literature.

아이뷰프로펜 이성질체에 대한 molecularly imprinted polymers의 binding 특성 (Binding Characteristics of Molecularly Imprinted Polymers for Ibuprofen Enantiomers)

  • 신명근;조규헌
    • KSBB Journal
    • /
    • 제14권3호
    • /
    • pp.273-278
    • /
    • 1999
  • The molecularly imprinted polymers(MIPs) synthesized at various polymerization conditions were examined as ibuprofen receptors in terms of binding characteristics. The 4-vinylpyridine polymers had 1.2 times higher adsorption capability for (S)-(+)-ibuprofen than the methacrylic acid polymers. The methacrylic acid polymers synthesized by UV radiation had 1.9 times higher selectivity for (S)-(+)-ibuprofen compared to those by thermal initiation. Effects of various solvents for binding were also examined in this research. According to the Scatchard analysis, the (S)-(+)-ibuprofen artificial receptors had two different kinds of binding sites for (S)-(+)-ibuprofen while having only single kind of binding site for ketoprofen. The binding sites of (S)-(+)-ibuprofen, n were calculated as 4.3~4.9 $\mu$mol/g and the dissociation constants, $K_D$ were 0.68 mM for the specific binding.

  • PDF

Apergillus niger LK 유래의 Epoxide Hydrolase 클로닝 및 특성 분석 (Cloning and Molecular Characterization of Epoxide Hydrolase from Aspergillus niger LK)

  • 이은열;김희숙
    • KSBB Journal
    • /
    • 제16권6호
    • /
    • pp.562-567
    • /
    • 2001
  • Styrene oxide 계열의 라세믹 에폭사이드 기질에 대한 입체선택적 가수분해능이 우수한 Aspergillus nigerr계열의 생촉매를 선발하였고, A.niger LK 유래의 EHase의 기질 특이성을 분석하였다. A. niger LK의 EHase는 benzene ring에 oxirane ring이 직접 연결되어 있는 styrene oxide, p-nitrostyrene oxide 기질에 대해서는 (R)-이성질체, benzene ring과 oxirane ring사이에 ether 등의 연결 chain이 있는 기질에 대해서는 (S)-이 성질체에 대한 입체선택적 가수분해능이 우수하였다. A niger LK의 EHase 유전자를 RT-PCR 방법으로 클로닝하였고, sequencing을 통해 다른 미생물 유래의 EHase와의 sequence identity 분석 등을 통해 특성을 분석하였다. Yeast 유래의 EHase와는 32% 수준의 sequence identity를 보였으며, Agrobacterisum, Corynebacterium 등의 박테리아 유래 EHase와는 identity가 매우 낮은 특성을 보였다. E. coli 숙주에서 발현된 재조합 EHase의 활성은 라세믹 에폭사이드 기질에 대한 입체선택적 가수분해 반응을 통해 확인할 수 있었다. 클러닝된 EHase의 보다 효율적인 발현 연구가 필요하며, 이러한 재조합 EHase는 고부가가치 광학활성 에폭사이드 제조를 위한 생물전환공정 시스템의 생촉매로 응용될 수 있을 것으로 기대된다.

  • PDF