Photoconversion of 7-dehydrocholesterol to vitamin D3 in synthetic phospholipid bilayers.

Abstract:

:The incorporation of 7-dehydrocholesterol into synthetic phospholipid bilayers altered the distribution of products after photolysis. In liposomes, the relative amounts of 7-dehydrocholesterol and lumisterol were elevated, and tachysterol was reduced from the levels observed in hexane solution. Z to E isomerization of the previtamin to tachysterol is favored in organic solvents. The inhibition of this process is evidence that an ordered lipid matrix places a new constraint on the conformation of the ring B fission product--one in which the configuration is favorable for a return to a cyclized diene. Further, rate enhancements of up to 15-fold were observed for the thermal isomerization of the previtamin to vitamin D3 in liposomes. The free energies of activation for the reaction at 25 degrees C were reduced by 1.3-1.5 kcal/mol in the bilayer environment compared to that of hexane. As this reaction involves the concerted transfer of a hydrogen via a cyclic intermediate, it provides additional evidence for membrane stabilization of an all-cis conformation of the previtamin. Photoproduct ratios were also studied for 7-dehydrocholesterol adsorbed to a variety of solid supports. That nonspecific interactions of 7-dehydrocholesterol with lipid can influence product formation may have important implications with respect to the mechanism of vitamin D3 biosynthesis.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Yamamoto JK,Borch RF

doi

10.1021/bi00334a039

subject

Has Abstract

pub_date

1985-06-18 00:00:00

pages

3338-44

issue

13

eissn

0006-2960

issn

1520-4995

journal_volume

24

pub_type

杂志文章
  • Sequence dependence for the energetics of dangling ends and terminal base pairs in ribonucleic acid.

    abstract::Stability increments of terminal unpaired nucleotides (dangling ends) and terminal base pairs on the core helixes AUGCAU and UGCGCA are reported. Enthalpy, entropy, and free energy changes of helix formation were measured spectrophotometrically for 18 oligoribonucleotides containing the core sequences. The results ind...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00388a058

    authors: Sugimoto N,Kierzek R,Turner DH

    更新日期:1987-07-14 00:00:00

  • Mechanism of transfer of reduced nicotinamide adenine dinucleotide among dehydrogenases. Transfer rates and equilibria with enzyme-enzyme complexes.

    abstract::The direct transfer of NADH between A-B pairs of dehydrogenases and also the dissociation of NADH from individual E-NADH complexes have been investigated by transient stopped-flow kinetic techniques. Such A-B transfers of NADH occur without the intermediate dissociation of coenzyme into the aqueous solvent environment...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00379a006

    authors: Srivastava DK,Bernhard SA

    更新日期:1987-03-10 00:00:00

  • Denaturation of cytochrome P450 2B1 by guanidine hydrochloride and urea: evidence for a metastable intermediate state of the active site.

    abstract::A metastable intermediate was found in the course of the denaturation of purified cytochrome P450 2B1 by increasing concentrations of guanidine hydrochloride (GuHCl). The metastable intermediate has no or low absorbance at 450 nm in the reduced carbon monoxide difference spectrum and has no absorbance at 420 nm. The i...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00016a023

    authors: Yu XC,Shen S,Strobel HW

    更新日期:1995-04-25 00:00:00

  • Fusion of phospholipid vesicles induced by muscle glyceraldehyde-3-phosphate dehydrogenase in the absence of calcium.

    abstract::Ca2+-induced fusion of phospholipid vesicles (phosphatidylcholine/phosphatidic acid, 9:1 mol/mol) prepared by ethanolic injection was followed by five different procedures: resonance energy transfer, light scattering, electron microscopy, intermixing of aqueous content, and gel filtration through Sepharose 4-B. The fi...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00329a015

    authors: Morero RD,Viñals AL,Bloj B,Farías RN

    更新日期:1985-04-09 00:00:00

  • Thermodynamics of ion-induced RNA folding in the hammerhead ribozyme: an isothermal titration calorimetric study.

    abstract::The hammerhead ribozyme undergoes a well-defined two-stage conformational folding process, induced by the binding of magnesium ions. In this study, we have used isothermal titration calorimetry to analyze the thermodynamics of magnesium binding and magnesium ion-induced folding of the ribozyme. Binding to the natural ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi002231o

    authors: Hammann C,Cooper A,Lilley DM

    更新日期:2001-02-06 00:00:00

  • Location of the catalytic site for phosphoenolpyruvate formation within the primary structure of Clostridium symbiosum pyruvate phosphate dikinase. 2. Site-directed mutagenesis of an essential arginine contained within an apparent P-loop.

    abstract::Pyruvate phosphate dikinase catalyzes the interconversion of adenosine 5'-triphosphate (ATP), orthophosphate (P(i)), and pyruvate with adenosine 5'-monophosphate (AMP), pyrophosphate (PP(i)), and phosphoenolpyruvate (PEP). The Arg 561 residue of Clostridium symbiosum PPDK is contained within a Gly-rich stretch of sequ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00007a012

    authors: Yankie L,Xu Y,Dunaway-Mariano D

    更新日期:1995-02-21 00:00:00

  • Identification of peptide antagonists to glycoprotein Ibalpha that selectively inhibit von Willebrand factor dependent platelet aggregation.

    abstract::GPIbalpha is an integral membrane protein of the GPIb-IX-V complex found on the platelet surface that interacts with the A1 domain of von Willebrand factor (vWF-A1). The interaction of GPIbalpha with vWF-A1 under conditions of high shear stress is the first step in platelet-driven thrombus formation. Phage display was...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi702428q

    authors: Benard SA,Smith TM,Cunningham K,Jacob J,DeSilva T,Lin L,Shaw GD,Kriz R,Kelleher KS

    更新日期:2008-04-22 00:00:00

  • Impact of Rett Syndrome Mutations on MeCP2 MBD Stability.

    abstract::Rett syndrome causing missense mutations in the methyl-CpG-binding domain (MBD) of methyl CpG-binding protein 2 (MeCP2) were investigated both in silico and in vitro to reveal their effect on protein stability. It is demonstrated that the vast majority of frequently occurring mutations in the human population indeed a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.5b00790

    authors: Kucukkal TG,Yang Y,Uvarov O,Cao W,Alexov E

    更新日期:2015-10-20 00:00:00

  • A Nuclear Resonance Vibrational Spectroscopic Study of Oxy Myoglobins Reconstituted with Chemically Modified Heme Cofactors: Insights into the Fe-O2 Bonding and Internal Dynamics of the Protein.

    abstract::The molecular mechanism of O2 binding to hemoglobin (Hb) and myoglobin (Mb) is a long-standing issue in the field of bioinorganic and biophysical chemistry. The nature of Fe-O2 bond in oxy Hb and Mb had been extensively investigated by resonance Raman spectroscopy, which assigned the Fe-O2 stretching bands at ∼570 cm-...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.8b00829

    authors: Ohta T,Shibata T,Kobayashi Y,Yoda Y,Ogura T,Neya S,Suzuki A,Seto M,Yamamoto Y

    更新日期:2018-12-04 00:00:00

  • Analysis of substrate-induced electronic, catalytic, and structural changes in inducible NO synthase.

    abstract::Inducible nitric oxide synthase (iNOS) catalyzes the NADPH-dependent formation of nitric oxide (NO) and citrulline from L-arginine and O2. In addition to serving as substrate, L-arginine alters the enzyme's heme iron spin equilibrium, increases its NADPH oxidation, and promotes assembly of active dimeric iNOS from ina...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi952844e

    authors: Sennequier N,Stuehr DJ

    更新日期:1996-05-07 00:00:00

  • Structural studies on the active site of Escherichia coli RNA polymerase. 2. Geometrical relationship of the interacting substrates.

    abstract::Since a major function of RNA polymerase must be to bring together substrates in the optimal configuration for internucleotide bond formation, studies have been undertaken to understand the geometrical relationship of the two substrates. A model has been constructed for the geometry of interaction of two ATP molecules...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00477a017

    authors: Beal RB,Pillai RP,Chuknyisky PP,Levy A,Tarien E,Eichhorn GL

    更新日期:1990-06-26 00:00:00

  • Molecular architecture of DesI: a key enzyme in the biosynthesis of desosamine.

    abstract::Desosamine is a 3-(dimethylamino)-3,4,6-trideoxyhexose found, for example, in such macrolide antibiotics as erthyromycin, azithromycin, and clarithromycin. The efficacies of these macrolide antibiotics are markedly reduced in the absence of desosamine. In the bacterium Streptomyces venezuelae, six enzymes are required...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi700751d

    authors: Burgie ES,Holden HM

    更新日期:2007-08-07 00:00:00

  • Composite organization of the cobalamin binding and cubilin recognition sites of intrinsic factor.

    abstract::Intrinsic factor (IF(50)) is a cobalamin (Cbl)-transporting protein of 50 kDa, which can be cleaved into two fragments: the 30 kDa N-terminal peptide IF(30) and the 20 kDa C-terminal glycopeptide IF(20). Experiments on binding of Cbl to IF(30), IF(20), and IF(50) revealed comparable association rate constants (k(+)(Cb...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi047936v

    authors: Fedosov SN,Fedosova NU,Berglund L,Moestrup SK,Nexø E,Petersen TE

    更新日期:2005-03-08 00:00:00

  • Chromium(III) modification of the first metal binding site of phosphoenolpyruvate carboxykinase.

    abstract::Chicken liver phosphoenolpyruvate carboxykinase (PEPCK) is activated by Cr2+ as the sole activator under anaerobic conditions. PEPCK was modified with Cr3+, starting with either Cr2+ or Cr3+. Cr3+ has the distinct advantage of being a paramagnetic cation that could serve as a paramagnetic probe. Activators Mn2+, Mg2+,...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9807299

    authors: Hlavaty JJ,Nowak T

    更新日期:1998-06-02 00:00:00

  • Analysis of DNA-dependent protein kinase-mediated DNA end joining by two-photon fluorescence cross-correlation spectroscopy.

    abstract::Nonhomologous end joining (NHEJ) is the primary mechanism by which mammalian cells repair DNA double-strand breaks (DSBs). Proteins known to play a role in NHEJ include the DNA-dependent protein kinase catalytic subunit (DNA-PKcs), the Ku 70/Ku 80 heterodimer (Ku), XRCC4, and DNA ligase IV. One of the main roles of th...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0524060

    authors: Merkle D,Block WD,Yu Y,Lees-Miller SP,Cramb DT

    更新日期:2006-04-04 00:00:00

  • A mechanochemical switch to control radical intermediates.

    abstract::B₁₂-dependent enzymes employ radical species with exceptional prowess to catalyze some of the most chemically challenging, thermodynamically unfavorable reactions. However, dealing with highly reactive intermediates is an extremely demanding task, requiring sophisticated control strategies to prevent unwanted side rea...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi500050k

    authors: Brunk E,Kellett WF,Richards NG,Rothlisberger U

    更新日期:2014-06-17 00:00:00

  • 1-Aminocyclopropanephosphonate: time-dependent inactivation of 1-aminocyclopropanecarboxylate deaminase and Bacillus stearothermophilus alanine racemase by slow dissociation behavior.

    abstract::1-Aminocyclopropanephosphonate (ACPP) was synthesized, and its effects on the pyridoxal 5'-phosphate linked enzymes 1-aminocyclopropanecarboxylate (ACPC) deaminase from Pseudomonas sp. ACPC and alanine racemase from Bacillus stearothermophilus were studied. ACPP was found to be a potent inhibitor of both enzymes with ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00386a025

    authors: Erion MD,Walsh CT

    更新日期:1987-06-16 00:00:00

  • Using fluorine nuclear magnetic resonance to probe changes in the structure and dynamics of membrane-active peptides interacting with lipid bilayers.

    abstract::The antimicrobial peptide MSI-78 serves as a model system for studying interactions of bioactive peptides with membranes. Using a series of MSI-78 peptides that incorporate l-4,4,4-trifluoroethylglycine, a small and sensitive (19)F nuclear magnetic resonance probe, we investigated how the local structure and dynamics ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi200639c

    authors: Suzuki Y,Buer BC,Al-Hashimi HM,Marsh EN

    更新日期:2011-07-12 00:00:00

  • Structure of the capsid of Kilham rat virus from small-angle neutron scattering.

    abstract::The structure of empty capsids of Kilham rat virus, an autonomous parvovirus with icosahedral symmetry, was investigated by small-angle neutron scattering. From the forward scatter, the molecular weight was determined to be 4.0 X 10(6), and from the Guinier region, the radius of gyration was found to be 105 A in D2O a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00321a044

    authors: Wobbe CR,Mitra S,Ramakrishnan V

    更新日期:1984-12-18 00:00:00

  • Catalytic mechanism of enterococcal kanamycin kinase (APH(3')-IIIa): viscosity, thio, and solvent isotope effects support a Theorell-Chance mechanism.

    abstract::Bacterial resistance to the aminoglycoside antibiotics is manifested primarily through the production of enzymes which covalently modify these drugs. The Enterococci and Staphylococci produce an ATP-dependent kinase, APH(3')-IIIa, which phosphorylates such antibiotics as kanamycin, amikacin, and neomycin, and this enz...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9603884

    authors: McKay GA,Wright GD

    更新日期:1996-07-02 00:00:00

  • DNA-stimulated assembly of oligomeric bacteriophage 434 repressor: evidence for cooperative binding by recruitment.

    abstract::Typical of many transcriptional regulatory proteins, the lambdoid bacteriophage repressors bind cooperatively to multiple sites on DNA. This cooperative binding is essential for establishment and maintenance of phage lysogeny. In the phage, two repressor homodimers, one bound at each of the adjacent operator sites, in...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi027318j

    authors: Ciubotaru M,Koudelka GB

    更新日期:2003-04-15 00:00:00

  • Assembly of an exceptionally stable RNA tertiary interface in a group I ribozyme.

    abstract::Group I intron RNAs contain a core of highly conserved helices flanked by peripheral domains that stabilize the core structure. In the Tetrahymena group I ribozyme, the P4, P5, and P6 helices of the core pack tightly against a three-helix subdomain called P5abc. Chemical footprinting and the crystal structure of the T...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi982113p

    authors: Doherty EA,Herschlag D,Doudna JA

    更新日期:1999-03-09 00:00:00

  • Mapping Functionally Important Residues in the Na+/Dicarboxylate Cotransporter, NaDC1.

    abstract::Transporters from the SLC13 family couple the transport of two to four Na+ ions with a di- or tricarboxylate, such as succinate or citrate. We have previously modeled mammalian members of the SLC13 family, including the Na+/dicarboxylate cotransporter NaDC1 (SLC13A2), based on a structure of the bacterial homologue Vc...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.7b00503

    authors: Colas C,Schlessinger A,Pajor AM

    更新日期:2017-08-22 00:00:00

  • The very low- and intermediate-density lipoprotein fraction isolated from apolipoprotein E-knockout mice transforms macrophages to foam cells through an apolipoprotein E-independent pathway.

    abstract::Apolipoprotein E (apoE)-knockout mice develop severe atherosclerosis associated with high levels of very low-density lipoprotein (VLDL) and intermediate-density lipoprotein (IDL) in plasma. To investigate the atherogenic role of VLDL and IDL, the lipoprotein fraction containing both VLDL and IDL (apoEko-VLDL/IDL) was ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi980762v

    authors: Hakamata H,Sakaguchi H,Zhang C,Sakashita N,Suzuki H,Miyazaki A,Takeya M,Takahashi K,Kitamura N,Horiuchi S

    更新日期:1998-09-29 00:00:00

  • Synthesis of lysogangliosides.

    abstract::The synthesis of gangliosides GM3, GM2, GM1, and GD1a solely lacking the fatty acid moiety, and thus called lysogangliosides in analogy to lysophospholipids, is described. Since a selective elimination of the fatty acid residue has not been achieved as yet, the gangliosides were first subjected to alkaline hydrolysis....

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00323a042

    authors: Neuenhofer S,Schwarzmann G,Egge H,Sandhoff K

    更新日期:1985-01-15 00:00:00

  • Evidence for the amphipathic nature and tilted topology of helices 4 and 5 in the closed state of the colicin E1 channel.

    abstract::The membrane-bound closed channel structure of helices 4 and 5 (Lys-406-Asp-446) of the colicin E1 channel domain was investigated by using a site-directed fluorescence labeling technique. A bimane probe was covalently attached to a cysteine residue in a series of single-cysteine mutant proteins to scan each helix in ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi801906v

    authors: Ho D,Merrill AR

    更新日期:2009-02-17 00:00:00

  • Unstructured RNA is a substrate for tRNase Z.

    abstract::tRNase Z, which exists in almost all cells, is believed to be working primarily for tRNA 3' maturation. In Escherichia coli, however, the tRNase Z gene appears to be dispensable under normal growth conditions, and its physiological role is not clear. Here, to investigate a possibility that E. coli tRNase Z cleaves RNA...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi051972s

    authors: Shibata HS,Minagawa A,Takaku H,Takagi M,Nashimoto M

    更新日期:2006-05-02 00:00:00

  • Crystallization and partial characterization of prenyltransferase from avian liver.

    abstract::Prenyltransferase (EC 2.5.1.1) has been obtained from chicken liver in a stable crystalline form. The enzyme has been shown to be homogeneous by polyacrylamide gel electrophoresis at pH 8.4, and by electrophoresis in sodium dodecyl sulfate containing gels. Electrofocusing of the crystalline enzyme results in a single ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00672a009

    authors: Reed BC,Rilling HC

    更新日期:1975-01-14 00:00:00

  • Effects of adenosine 5'-diphosphate on bovine glutamate dehydrogenase: diethyl pyrocarbonate modification.

    abstract::Initial rate kinetic studies and reduced coenzyme binding studies with bovine glutamate dehydrogenase have shown that an enzyme-NAD(P)H-glutamate abortive complex is a major participant in the overall enzyme-catalyzed reaction. The allosteric regulator ADP is shown to activate the enzyme by destabilizing this abortive...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00567a017

    authors: George A,Bell JE

    更新日期:1980-12-23 00:00:00

  • Reevaluation of interaction of cis-dichloro(ethylenediamine)platinum(II) with DNA.

    abstract::Intrastrand cross-links represent the majority of modifications in DNA resulting from interaction with the cancer chemotherapeutic drug cis-diamminedichloroplatinum(II) (cis-DDP). These adducts were recently characterized although several discrepancies remained to be resolved. In these studies, [3H]-cis-dichloro(ethyl...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00361a026

    authors: Eastman A

    更新日期:1986-07-01 00:00:00