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PubMed1990

Synthetic probes for the alpha-factor receptor.

The binding of the tridecapeptide yeast mating pheromone, alpha-factor, to its receptor represents an excellent model for the investigation of peptide hormone-receptor interactions. In this paper we present a number of strategies to probe the binding site of the alpha-factor receptor, and discuss the synthesis of probes containing radioactive and affinity tags. Preferential acylation of the alpha- or epsilon-amine in [Nle12]-alpha-factor was accomplished using 3-[3,5-diiodo-4-hydroxyphenyl] propanoic acid hydroxysuccinimide ester (diiodo Bolton-Hunter reagent). At pH 8.0 in a N-N-dimethylformamide/water mixture the ratio of epsilon- to alpha-acylation was 2.15 to 1, whereas at pH 6.5 in a 1,2-dimethoxyethane/water mixture alpha-acylation was favored by more than 3 to 1. The product distribution was found to depend on pH, organic cosolvent, and the ratio of organic solvent and aqueous buffer. Product distributions were followed using analytical high performance liquid chromatography and the products were characterized enzymatically and by mass spectrometry. Citraconic anhydride preferentially alpha-acylated [Nle12]-alpha-factor and served as a temporary masking group during the synthesis of epsilon-Bolton-Hunter acylated pheromone. Biotin or diiodo Bolton-Hunter reagents were also directly incorporated into [Nle12]-alpha-factor or Lys[Nle12]-alpha-factor during peptide synthesis. The peptides were assembled on a chloromethyl polystyrene resin or on a (phenylacetamido)methyl resin, and cleaved using anhydrous hydrogen fluoride (HF). Probes were inserted on amino groups either prior (biotin) or subsequent (Bolton-Hunter reagent) to HF cleavage. The biological activity of the synthetic peptides was characterized using growth arrest assays.(ABSTRACT TRUNCATED AT 250 WORDS)

Amino Acid Sequence↗

PubMed1991

Molecular and crystal structures of Aib-containing oligopeptides Boc-Leu4-Aib-Leu4-OBzl and Boc-(Leu4-Aib)2-OBzl.

Sample peptides Boc-Leu4-Aib-Leu4-OBzl and Boc-(Leu4-Aib)2-OBzl, were crystallized by the solvent-evaporation method. Both crystals are monoclinic, with space group of P2(1) and Z = 2. The cell parameters are a = 16.580 (7), b = 21.105 (7), c = 11.583 (4) A, and beta = 104.90 (3) degrees (Boc-Leu4-Aib-Leu4-OBzl), and a = 15.247 (9), b = 19.04 (1), c = 16.311 (9) A, and beta = 117.10 (1) degrees [Boc-(Leu4-Aib)2-OBzl]. Crystal structures were solved by the direct method and refined to R values of 0.096 (the former peptide) and 0.112 (the latter). Peptide backbones fold into a right-handed alpha-helix, except for the C-terminal Aib residue in Boc-(Leu4-Aib)2-OBzl. Both peptide molecules are stabilized by six (the former) or seven (the latter) intramolecular (5----1) hydrogen bonds, and arranged in the head-to-tail fashion, which makes an infinite column. In this column, one (the former) or two (the latter) intermolecular hydrogen bonds link the neighboring molecules. In the case of Boc-Leu4-Aib-Leu4-OBzl, the solvent molecule N,N-dimethylformamide was found in the difference Fourier map. There was a hydrogen bond between peptide and solvent molecule. Along the lateral direction, only hydrophobic contacts were observed between adjacent peptide molecules.

Amino Acid Sequence↗

PubMed1992

A synthetic analogue for the active site of plant-type ferredoxin: two different coordination isomers by a four-cys-containing [20]-peptide.

The (Fe2S2)2+ complex of an artificial 20-peptide ligand, Ac-Pro-Tyr-Ser-Cys-Arg-Ala-Gly-Ala-Cys-Ser-Thr-Cys-Ala-Gly-Pro-Leu-Leu-T hr-Cys- Val-NH2, containing an invariant Cys-A-B-C-D-Cys-X-Y-Cys (A, B, C, D, X, Y = amino acid residues) fragment of plant-type ferredoxins was synthesized by a ligand exchange method with [Fe2S2(S-t-Bu)4]2-. 1H-nmr spectroscopic and electrochemical data of the complex indicate the presence of two coordination isomers. One of them having a Cys-X-Y-Cys bridging coordination to the two Fe(III) ions, has the (Fe2S2)2+ core environment similar to those of the denatured plant-type ferredoxins and exhibits a positive shifted redox potential at -0.64 V vs saturated colonel electrode (SCE) in N,N-dimethylformamide (DMF). Another isomer with the Cys-A-B-C-D-Cys bridging coordination shows a negative redox potential at -0.96 V vs SCE in DMF.

Amino Acid Sequence↗

PubMed1994

Redox-active bis-cysteinyl peptides. I. Synthesis of cyclic cystinyl peptides by conventional methods in solution and on solid supports.

Cyclic mono-cystinyl active-site fragments of thioredoxin and thioredoxin reductase were synthesized as N-acetyl and C-amide octapeptides by conventional methods of peptide synthesis in solution and on solid supports. Using a side-chain protection based on acid-labile tert-butanol-derived groups and on the S-tert-butylthio unsymmetric disulfide for the thiol functions, in combination with N alpha-Z- or N alpha-Nps derivatives in the chain elongation steps, the synthesis in solution was carried out in straightforward manner yielding the fully protected octapeptides as well characterized compounds. Upon deprotection with trifluoroacetic acid and reduction of the unsymmetrical disulfides with tri-butylphosphine, the resulting bis-cysteinyl-octapeptides were oxidized in dimethylformamide with azodicarboxylic acid di-tert-butyl ester to produce the desired cyclic compounds in good overall yields. For the synthesis on solid supports a similar acid-labile side-chain protection was applied in combination with the N alpha 9-flourenylmethyoxycarbonyl derivatives in the chain elongation steps. Thereby acylations were performed with the related amino acid N-carboxyanhydrides (UNCAs) or by the O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium-tetraf luoroborate/1- hydroxybenzotriazole (TBTU/HOBt) procedure. The solid phase synthesis of the two octapeptides led to unexpected difficulties in terms of recovery of peptidic material from the resins in the final acidolytic cleavage step as well as of racemization at the level of the cysteine residues by the TBTU/HOBt coupling method. Racemization was efficiently suppressed by employing the related pentafluorophenyl ester and this method led to crude octapeptide products of a degree of purity comparable to those obtained by the synthesis in solution. However, the recovery of the peptides from the resin, i.e., irreversible reattachment of cleaved peptidic material via alkylation of various side-chain functions, could not be avoided even using the most efficient scavengers or their cocktails.

Amino Acid Sequence↗

PubMed2002

A strategy for in vivo screening of subtilisin E reaction specificity in E. coli periplasm.

We developed a protocol for efficient expression of the functional serine protease, subtilisin E, in Escherichia coli periplasm that permits direct in vivo measurement of the enzyme's catalytic activity. Activity assays and SDS-PAGE/Western blot analysis showed that the levels of expressed subtilisin varied and were correlated with both the culture conditions and the induction procedures. The highest level of subtilisin expression was achieved at 0.10-0.15% (w/v) of arabinose as inducer and a temperature of 20-22 degrees C, and was ca. eightfold higher as compared to the expression level at 30 degrees C. Cultivation of bacterial cells to a steady state of balanced growth before induction was required for uniform subtilisin expression in cell cultures growing in wells of microtiter plates. Amidase and esterase cell-based kinetic assays on microtiter plates were developed based on the direct measurement of subtilisin activity in vivo. Intact E. coli cells displaying wild-type, dimethylformamide-resistant, and temperature-resistant subtilisins were assayed on N-succinyl-Ala-Ala-Pro-Phe-p-nitroanilide and N-acetyl-Phe-p-nitrophenyl ester for their amidase and esterase activity, respectively. Additionally, the periplasmic fractions were isolated from the three E. coli strains expressing the respective subtilisins and tested for amidase activity. The amidase activity of the three subtilisins was ca. 15-fold higher than the esterolytic activity when measured in both the intact cells and in the periplasmic fractions. The strategy combining periplasmic expression of subtilisins with two cell-based kinetic assays permits rapid screening of subtilisin mutant libraries for desired activities.

Amidohydrolases↗

PubMed2003

Effects of phthalic anhydride modification on horseradish peroxidase stability and activity.

Phthalic anhydride (PA) modification stabilizes horseradish peroxidase (HRP) by reversal of the positive charge on two of HRP's six lysine residues. Native and PA-HRP had half-inactivation temperatures of 51 and 65 degrees C and half-lives at 65 degrees C of 4 and 17 min, respectively. PA-HRP was more resistant to dimethylformamide at room temperature and tetrahydrofuran at 60 degrees C and to unfolding by heat, guanidine chloride, EDTA, and the reducing agent tris(2-carboxyethyl)phosphine hydrochloride. Binding of the hydrophobic probe Nile Red to the native enzyme and to PA-HRP was similar. The kinetics of both HRPs with the substrates ABTS, ferrocyanide, ferulic acid, and indole-3-propionic acid were measured, as was binding of the inhibitor benzhydroxamic acid. Small improvements in the catalytic properties were detected.

Binding Sites↗

PubMed2003

Multienzyme catalysis in microfluidic biochips.

The attachment of enzymes to glass microfluidic channels has been achieved using a highly reactive poly(maleic anhydride-alt-alpha-olefin) (PMA)-based coating that is supplied to the microchannel in a toluene solution. The PMA reacts with 3-aminopropyltriethoxysilane groups linked to the glass surface to form a matrix that enables additional maleic anhydride groups to react with free amino groups on enzymes to give a mixed covalent-noncovalent immobilization support. Using a simple T-channel microfluidic design, with reaction channel dimensions of 200 microm wide (at the center), 15 microm deep, and 30 mm long giving a reaction volume of 90 nL, soybean peroxidase (SBP) was attached at an amount up to 0.6 microg/channel. SBP-catalyzed oxidation of p-cresol was performed in aqueous buffer (with 20% [v/v], dimethylformamide) containing H(2)O(2), with microfluidic transport enabled by electroosmotic flow (EOF). Michaelis-Menten kinetics were obtained with K(m) and V(max) values of 0.98 mM and 0.21 micromol H(2)O(2) converted/mg SBP per minute, respectively. These values are nearly identical to nonimmobilized SBP kinetics in aqueous-DMF solutions in 20-microL volumes in 384-well plates and 5-mL reaction volumes in 20-mL scintillation vials. These results indicate that SBP displays intrinsically native activity even in the immobilized form at the microscale, and further attests to the mild immobilization conditions afforded by PMA. Bienzymic and trienzymic reactions were also performed in the microfluidic biochip. Specifically, a combined Candida antarctica lipase B-SBP bienzymic system was used to convert tolyl acetate into poly(p-cresol), and an invertase-glucose oxidase SBP trienzymic system was used to take sucrose and generate H(2)O(2) for SBP-catalyzed synthesis of poly(p-cresol).

Catalysis↗

PubMed2004

Laboratory evolution of cytochrome p450 BM-3 monooxygenase for organic cosolvents.

Cytochrome p450 BM-3 (EC 1.14.14.1) catalyzes the hydroxylation and/or epoxidation of a broad range of substrates, including alkanes, alkenes, alcohols, fatty acids, amides, polyaromatic hydrocarbons, and heterocycles. For many of these notoriously water-insoluble compounds, p450 BM-3's K(m) values are in the millimolar range. Polar organic cosolvents are therefore added to increase substrate solubility and achieve high catalytic efficiency. Using p450 BM-3 as a catalyst for these important transformations requires that we improve its ability to tolerate the cosolvents. By directed evolution, we improved the activity of p450 BM-3 in the presence of dimethylsulfoxide (DMSO) and tetrahydrofuran (THF), achieving increases in specific activity up to 10-fold in 2% (v/v) THF and 6-fold in 25% (v/v) DMSO. The engineered p450 BM-3's are also significantly more resistant to acetone, acetonitrile, dimethylformamide, and ethanol as cosolvents in the reaction.

Bacillus megaterium↗

PubMed2007

The stability of engineered thermostable neutral proteases from Bacillus stearothermophilus in organic solvents and detergents.

Engineered extremely thermostable variants of the thermolysin-like protease from Bacillus stearothermophilus possessing an introduced disulfide bond G8C/N60C (double mutant, DM) and six additional amino acid substitutions in the exposed loop region 56-69 (Boilysin, BLN) have been probed with respect to stability toward water-miscible organic solvents and detergents. The solvent concentrations where 50% of enzyme activity were irreversibly lost (C(50)) decreased in the order methanol > 2-propanol > dimethylsulfoxide > dioxane > acetonitrile > dimethylformamide > acetone. The C(50) values were remarkably higher for the thermostable variants than for the wild-type enzymes. Therefore, the stabilization of this loop region also protects the molecule from irreversible inactivation by solvents, and inactivation seems to follow principally the same mechanism as thermal inactivation. However, in contrast to thermal inactivation where the corresponding T(50) values of DM and BLN differed by 10 K, the differences of the C(50) values of DM and BLN were not significant. Detergents had great effects on proteolytic activities which were dependent on the individual detergent and its concentration, but mostly without significant differences between the enzyme variants. These effects were inactivating (SDS, sulfobetaine) or strongly activating (CTAB, CHAPS). Triton X-100 and Tween 20 were activating or inactivating at low and high concentrations, respectively. In all detergents, stabilities of the enzymes were strongly decreased. However, the more thermostable variants were affected by the detergents to the same extent as the wild-type enzymes suggesting that the mechanism of detergent inactivation is different from that of thermal inactivation.

Amino Acid Sequence↗

PubMedDate not supplied

Determination of free fatty acids in blood, tagged with 4-(2-carbazoylpyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl )- 2,1,3-benzoxadiazole, by high-performance liquid chromatography with fluorescence detection.

The free fatty acids in blood were determined by high performance liquid chromatography (HPLC) after pre-column tagging with 4-(2-carbazoylpyrrolidin-1-yl)- 7-(N,N-dimethylaminosulphonyl)-2,1,3-benzoxadiazole [sequence: see text] (DBD-ProCZ). The tagging conditions were optimized with palmitic acid (C16:0) and linoleic acid (C18:2) as representative free fatty acids, saturated and unsaturated, respectively. Under the mild reaction conditions of room temperature for 90 min in dimethylformamide (DMF) containing 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC, 0.2 M)/pyridine (2%), all the fatty acids tested were tagged with the DBD-ProCZ to produce highly fluorescent derivatives which emit light at 550 nm (excitation at 450 nm). The fluorescence wavelengths were essentially the same for all fatty acids, whereas the intensities were different for individual fatty acids. The derivatives obtained from ten free fatty acids were completely separated by reversed-phase chromatography with two isocratic elution conditions. The on-column detection limit (signal-to-noise ratio of 3) with proposed HPLC separation and fluorescence detection is in the range of 19 (palmitic acid)--176 fmol (palmitoleic acid). The free fatty acids in rat serum and human plasma were successfully determined using the present methods.

Animals↗

PubMed1976

The gas chromatographic mass spectrometric determination of trifluoroacetic acid in biological fluid. Application to halothane metabolism.

The methyl ester of trifluoroacetic acid was prepared by reaction with N,N'-dimethylformamide dimethylacetal and was successfully passed through a gas chromatograph. Trifluoroacetic acid was detected by the use of gas chromatography and low and high resolution gas chromatography mass spectrometry in an acidic extract of an incubation medium containing microsomes, reduced nicotinamide adenine dinucleotide phosphate, oxygen and halothane. However, trifluoroacetic acid could not be detected when nicotinamide adenine dinucleotide or oxygen was omitted from the incubation system. From these results, it was proved that halothane is oxidatively metabolized to trifluoroacetic acid by hepatic microsomes.

Animals↗

PubMed1979

Detection of the in vivo conversion of 2-pyrrolidinone to gamma-aminobutyric acid in mouse brain.

Labeled gamma-aminobutyric acid was detected in mouse brain following intravenous injections of deuterium labeled 2-pyrrolidinone. [2H6]Pyrrolidinone was prepared by the reduction of [2H4]succinimide with lithium aluminum deuteride. Quantification was accomplished by a gas chromatography mass spectrometry assay method. gamma-Aminobutyric acid and internal standard, 5-aminovaleric acid, were converted to volatile derivatives by treatment with N,N-dimethylformamide dimethyl acetal. Quantitative estimates were derived from peak area measurements obtained from monitoring the parent ions of the gamma-aminobutyric acid and internal standard derivatives by repetitive scanning during the GC run. The conversion of pyrrolidinone to gamma-aminobutyric acid may provide a method for labeling central gamma-aminobutyric acid pools.

Animals↗

PubMed1980

Applications of deuterium labeling in the study of the in vitro conversion of delta 1-pyrroline to 4-aminobutanoic acid and 2-pyrrolidinone.

delta 1-Pyrroline is a putrescine metabolite that is biotransformed by rabbit liver preparations to 4-aminobutanoic acid and its lactam, 2-pyrrolidinone. Analysis of dilute aqueous solutions of delta 1-pyrroline by proton nuclear magnetic resonance indicated the the predominating species in the liver incubation preparations was delta 1-pyrroline monomer, although other species, such as 4-aminobutyraldehyde an delta 1-pyrroline timer, may exist in equilibrium with the monomer. [2H12]-delta 1-Pyrroline trimer was synthesized from [2H5]pyrrolidine by conversion to the N-chloro derivative followed by dehydrohalogenation. 4-Aminobutanoic acid was measured by a gas chromatographic mass spectrometric assay after derivatization with dimethylformamide dimethyl acetal. The 4-aminobutanoic acid homologue, 5-aminovaleric acid, served as internal standard. 2-Pyrrolidinone was hydrolyzed and measured as 4-aminobutanoic acid. A comparison of the amounts of product formed following incubation of labeled and unlabeled delta 1-pyrroline indicated a significant isotope effect in the formation of 2-pyrrolidinone. The influence of the label was much less on 4-aminobutanoic acid production. The results suggest that there are two separate pathways involved in the reaction.

Animals↗

PubMed1980

Determination of nanogram amounts of the antiarrhythmic drug Org 6001 in biological fluids and tissues using selected ion monitoring.

An assay method has been developed to determine the free base of Org 6001 (3 alpha-amino-5 alpha-androstan-2 beta-ol-17-one . HCl) in biological samples. The assay procedure consists of protein denaturation, ethyl acetate extraction, derivatization with tert-butyldimethylchlorosilane in dimethylformamide followed by n-hexane extraction and selected ion monitoring using trideuterated Org 6001 as an internal standard. For quantitation, the signals were monitored corresponding to the masses of the [M - 57]+ ions of 2-O-tert-butyldimethylsilyl, N-formyl derivatives of Org 6001 and the internal standard at m/z 390 and m/z 393, respectively. The assay method was applied to plasma samples from the human and rat, and to rat tissues including the target organ, the heart. The relationship between the Org 6001 plasma level and clinical effect in the human, the distribution of Org 6001 in rat tissues, and the correlation between the plasma level and the amount of Org 6001 in total heart tissue of the rat were determined.

Androstanols↗

PubMed1988

Octafluorotoluene as a derivatizing agent for steroids in human plasma.

The use of octafluorotoluene (OFT) as a versatile gas chromatographic/mass spectrometric derivatizing agent for steroids containing alcoholic, phenolic or alpha, beta-unsaturated keto functions, is described. Two distinct derivatizing schemes can be utilized, involving (method 1) a phase-transfer reaction, employing a two-phase system of CH2Cl2 and N NaOH with n-Bu4NHSO4 as catalyst (suitable for alcoholic and phenolic steroids) and (method 2) a reaction conducted in anhydrous dimethylformamide at 155 degrees C with CsF as base (appropriate for alpha, beta-unsaturated keto steroids). Perfluorotolyl (PFT) ethers and/or enol ethers have thus been generated. The electron impact spectra display abundant high-mass molecular ions where derivatization has occurred at a phenolic or enolic function. An extraction, derivatization and gas chromatographic/mass spectrometric scheme has been devised involving method 2 for the analysis of steroids in human plasma. A preliminary quantitative investigation of the levels of testosterone in plasma has been carried out employing these methods. The anomalously high level found is explained in terms of the presence in plasma of lipid-soluble derivatives of testosterone (probably fatty acid esters) which generate the testosterone bis-OFT derivative under the reaction conditions employed.

Androstadienes↗

PubMed2004

Group 1 coordination chains and hexagonal networks of host cyclotriveratrylene with halogenated monocarbaborane anions.

Halogenated carbaborane ions [CB(11)H(6)X(6)](-) in which X=Cl or Br have been combined with the host molecule cyclotriveratrylene (CTV) and Group 1 metal cations to give crystalline materials. The complexes [Na(ctv)(H(2)O)(CB(11)H(6)X(6))](CF(3)CH(2)OH) feature chiral Na-CTV coordination chains with complexation of the [CB(11)H(6)X(6)](-) ion by the Na(+) ion, together with the CTV molecular cavity. The coordination chains are hydrogen bonded together to give a puckered two-dimensional hexagonal grid structure. [K(ctv)(CB(11)H(6)Cl(6))(CF(3)CH(2)OH)(0.5)] is essentially isostructural. Complexes [Rb(ctv)(CB(11)H(6)Br(6))(H(2)O)] and [Cs(ctv)(CB(11)H(6)X(6))(CH(3)CN)] are coordination polymers with related distorted hexagonal grid structures. Use of N,N'-dimethylformamide (DMF) as a solvent results in an entirely different type of assembly, with [Na(2)(dmf)(4)(H(2)O)(2)(ctv)][(dmf)(0.5)(ctv)][CB(11)H(6)Br(6)](2) showing unusual [Na-mu-(dmf)-Na] bridges, and once again forming a distorted hexagonal coordination polymer.

Journal Article↗

PubMed2004

Poly(phenylacetylene)s bearing a peptide pendant: helical conformational changes of the polymer backbone stimulated by the pendant conformational change.

Optically active, cis-transoid poly(phenylacetylene) derivatives bearing a poly(gamma-benzyl-L-glutamate) [poly(PBGAm)] or poly(L-glutamic acid) [poly(PGAm)] chain as the pendant were prepared by polymerisation of the corresponding macromonomer with a rhodium catalyst followed by hydrolysis of the pendant ester groups. Their conformational changes in solution, induced by a helix-coil transition of the pendant polypeptides, were investigated using circular dichroism (CD) and absorption spectroscopies. A series of macromonomers with a different peptide chain lengths was synthesised by the polymerisation of the N-carboxyanhydride of gamma-benzyl-L-glutamate with a phenylacetylene bearing an alanine residue as the initiator. The obtained macromonomers (PBGAm) were further polymerised with a rhodium catalyst in N,N-dimethylformamide (DMF) to yield novel poly(phenylacetylene)s [poly(PBGAm)] with a poly(gamma-benzyl-L-glutamate) pendant. The poly(PBGAm) exhibited an induced circular dichroism (ICD) in the UV/Vis region of the polymer backbone in dimethyl sulfoxide (DMSO), probably due to the prevailing one-handed helix formation. The Cotton effect signs of a DMSO solution of the poly(PBGAm) were inverted and accompanied by a visible colour change in the presence of an increasing amount of chloroform or DMF containing lithium chloride. The results suggest that poly(PBGAm) may undergo a conformational change such as a helix-helix transition with a different helical pitch responding to a change in the alpha-helix content of the poly(gamma-benzyl-L-glutamate) pendant. Moreover, a water-soluble poly(PGAm) also showed a similar, but dramatic change in its helical conformation with a visible colour change stimulated by a helix-coil transition of the pendant poly(L-glutamic acid) chains by changing the pH in water.

Acetylene↗

PubMed2005

Structural rationalisation of co-crystals formed between trithiocyanuric acid and molecules containing hydrogen bonding functionality.

Crystallisation of trithiocyanuric acid (TTCA) from various organic solvents that have hydrogen bonding capability (acetone, 2-butanone, dimethylformamide, dimethyl sulfoxide, methanol and acetonitrile) leads to the formation of co-crystals in which the solvent molecules are incorporated together with TTCA in the crystal structure. Structure determination by single-crystal X-ray diffraction reveals that these co-crystals can be classified into different groups depending upon the topological arrangement of the TTCA molecules in the crystal structure. Thus, three different types of single-tape arrangements of TTCA molecules and one type of double-tape arrangement of TTCA molecules are identified. In all co-crystals, hydrogen-bonding interactions are formed through the involvement of N-H bonds of TTCA molecules in these tapes and the other molecule in the co-crystal. Detailed rationalisation of the structural properties of these co-crystals is presented.

Journal Article↗