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PubMed1995

Low cerebrospinal fluid concentrations of peptide histidine valine and somatostatin-28 in Alzheimer's disease: altered processing of prepro-vasoactive intestinal peptide and prepro-somatostatin.

Recent studies have indicated that deposition of beta amyloid peptide in the brains of patients with senile dementia of the Alzheimer type (SDAT) is a consequence of abnormal processing of the beta amyloid protein precursor. In addition, reduced concentrations of various peptides have been measured in post-mortem brain tissue and cerebrospinal fluid (CSF) of patients with SDAT. We determined concentrations of the peptides derived from prepro-vasoactive intestinal peptide (VIP)--peptide histidine methionine-27 (PHM-27), peptide histidine valine (PHV) and VIP--and peptides derived from prepro-somatostatin (prepro-SS), SS-14 and SS-28, in CSF of patients with SDAT by radioimmunoassay combined with high performance liquid chromatography. We found significantly reduced levels of total PHM-immunoreactivity (IR) and PHV, and unaltered levels of PHM-27 and VIP in SDAT, compared with those in controls. Total SS-IR and SS-28 concentrations were significantly reduced in SDAT, while SS-14 levels did not differ from those of controls. These results suggest that an altered processing of the prepro-peptides of VIP and SS may occur in SDAT and that these alterations might have a significant role in the pathogenesis of SDAT.

Aged↗
PubMed1984

Trace metal requirements in total parenteral nutrition (TPN). 5. Formation constants for the copper(II)--histidine ternary complexes with threonine, lysine, glycine, phenylalanine, valine, and cystine, and discussion of their implications regarding the copper distribution in blood plasma during TPN and the evaluation of the daily dose of copper.

Specific metal deficiencies have been reported to affect patients receiving total parenteral nutrition (TPN). Our previous studies on the topic were devoted to the computer-based interpretation of the extra urinary excretion of zinc; a theoretical approach was also proposed, with a view to compensating for the extra losses of this metal. Similarly, the present work deals with the problem of TPN-induced copper deficiency and its remedy. As is the case for zinc, the TPN-induced excretion of copper clearly stems from the relative mobilization of the plasma protein-bound pool of this metal into its diffusable low-molecular-weight fraction; this phenomenon being due to the competitive complexation of copper by the amino acids of the nutritive solution. The computer simulation of this effect thus required that first the equilibrium constants be experimentally determined for the main complexes of copper that might form in the solution as well as in plasma during the infusion. Accordingly, complex formation in the copper-histidine ternary systems with threonine, lysine, glycine, phenylalanine, valine, and cystine was investigated by potentiometry at 37 degrees C in NaCIO4 0.15 mol X dm-3. The implications of the results obtained are discussed with regard to the interpretation of the copper excretion and the estimation of the desirable daily dose of this metal for the TPN mixture under consideration.

Amino Acids↗
PubMed1990

Heart rate response to peptide histidine valine in human subjects is not mediated through beta receptors.

Peptide histidine valine (PHV) is a 42 amino acid polypeptide closely related to the neuropeptides VIP, PHI and PHM. We have performed a placebo-controlled, double-blind study to assess the hypothesis that the cardiovascular response to PHV infusion may be mediated via the sympathetic nervous system. Four subjects received atenolol or matched placebo 90 min prior to a controlled incremental infusion of PHV, with monitoring of heart rate, blood pressure and skin temperature. Following placebo all subjects showed a dose-related increase in heart rate and skin temperature with no effect on blood pressure during PHV infusion. beta-Blockade had no effect on skin temperature response. Pre-treatment with atenolol reduced the resting blood pressure and the maximum heart rate achieved, but did not affect the percentage increase in heart rate during PHV infusion. This suggests that the action of PHV does not involve beta-receptors. The lack of effect of PHV infusion on blood pressure, despite tachycardia and marked cutaneous vasodilatation, implies that PHV has a different effect on the resistance vessels from that of other peptides such as VIP.

Adult↗
PubMed1992

Peptide histidine valine (PHV) is present and biologically active in the human female genital tract.

The occurrence of vasoactive intestinal polypeptide (VIP), peptide histidine methionine (PHM) and peptide histidine valine (PHV) in the human female genital tract was studied by means of radioimmunoassay in combination with gel chromatography. In addition, the effect of PHV on genital smooth muscle activity was investigated in vitro and compared to that of VIP. Immunoreactive VIP, PHM and PHV were present in all regions of the human female genital tract, the highest concentrations being measured in the vagina and the uterine cervix. The peptides displayed similar regional distribution and as expected from the structure of the VIP precursor molecule in which the examined peptides are contained, the molar ratio of VIP to the total PHM/PHV immunoreactivity was close to 1:1. In all regions PHV constituted 50-70% of the total PHM/PHV immunoreactivity indicating that the dibasic conversion site after PHM was uncleaved. VIP and PHV were found to be equipotent relaxants of the smooth muscle from the Fallopian tube and the myometrium. The present study indicates that PHV like PHM and VIP may act as a neurotransmitter in the human female genital tract and thus participate in the local nervous control of the reproductive functions.

Adult↗
PubMedDate not supplied

Effect of alpha-MSH 11-13 (lysine-proline-valine) on fever in the rabbit.

In previous experiments, alpha-MSH (1-13) and ACTH (1-24), which contains the alpha-MSH 1-13 amino acid sequence, were found to reduce fever after central and peripheral administration of low, non-hypothermic doses. Shorter molecules, including alpha-MSH 1-10, had no effect. The idea that the 11-13 amino acid sequence is important to the effect of the parent molecule was tested by giving lysine-proline-valine both centrally and peripherally to rabbits made febrile by IV administration of leukocytic pyrogen. The tripeptide reduced fever after both central (0.5-2.0 mg) and peripheral (2-200 mg) administration. It appears that the 11-13 sequence is part of the message sequence of alpha-MSH with regard to antipyretic activity. However, the lower potency relative to that of the parent molecule suggests that other portions of the molecule are essential to full expression of the antipyretic effect.

Animals↗
PubMed1989

Regulation of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine and isopenicillin N biosynthesis in Penicillium chrysogenum by the alpha-aminoadipate pool size.

The effect of changes in the intracellular concentration of alpha-aminoadipate on the formation of alpha-aminoadipyl-cysteinyl-valine (ACV) and isopenicillin N (IPN)--two intermediates of penicillin biosynthesis--by strains of Penicillium chrysogenum has been investigated by measuring the incorporation of radioactivity from (6-14C)-alpha-aminoadipate into cellular 14C-ACV and 14C-IPN. No ACV or IPN were found in any strain during cultivation on glucose, but were clearly detected in all three strains during growth on lactose, displaying increased formation in strains exhibiting increased penicillin productivity and increased intracellular alpha-aminoadipate pools. ACV and IPN formation was affected by subjected P. chrysogenum mycelia to either general amino acid control (by addition of amitrol) or by exogenous addition of 5 mM L-lysine. In all cases, the changes observed paralleled the changes in the intracellular alpha-aminoadipate pool. These results are consistent with the alpha-aminoadipate pool limiting the biosynthesis of ACV and IPN and hence penicillin biosynthesis in the present strains of P. chrysogenum.

2-Aminoadipic Acid↗
PubMed1990

Analysis of delta-L-alpha-aminoadipyl-L-cysteinyl-D-valine by ion chromatography and pulsed amperometric detection.

A novel high-performance liquid chromatography (HPLC) method is presented for the detection and trace level determination of the tripeptide delta-L-alpha-aminoadipyl-L-cysteinyl-D-valine (ACV). The tripeptide, an intermediate in penicillin production, is derived from fungal fermentation. The technique relies on ion-exchange separation of the tripeptide on an anion-exchange column followed by detection by reduction on a gold electrode using pulsed amperometry. The sensitivity of direct determination of ACV is increased by employing pulsed amperometric detection (PAD) over direct ultraviolet detection. Choice of the working electrode and optimisation of electrode potentials was based on cyclic voltammograms recorded for the tripeptide in the mobile phase. A linear regression equation was obtained over the range 0-100 micrograms ml-1. The detection limit in fermentation broths was found to be 0.1 micrograms ml-1 whereas in buffer the detection limit was found to be 10 ng ml-1. A good correlation coefficient was observed when ACV concentrations determined by ion chromatography-PAD were compared with measurements obtained by pre-column derivatisation with fluoromethylorthochloroformate followed by HPLC separation on a reversed-phase C18 silica column with UV detection. The procedure has been applied to the measurement of natural levels of ACV in fermentation broths of selected strains of Aspergillus nidulans and Penicillin chrysogenum.

Aspergillus nidulans↗
PubMed1989

High-performance liquid chromatographic determination of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine in complex media by precolumn derivatisation with dansylaziridine.

A novel method is described for the trace level quantitation of the tripeptide delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine (ACV) in complex fermentation media, using a high-performance liquid chromatographic, pre-column derivatisation technique. The procedure is based upon the reaction of the ACV monomer with 5-dimethylaminonaphthalene-1-sulphonylaziridine (dansylaziridine) and produces a highly fluorescent product. Reaction conditions between the reagent and tripeptide were investigated and optimal conditions established. Linear calibration graphs were obtained over the ranges 227-0.56 micrograms/ml and 227-5.6 ng/ml. The extracellular ACV levels produced in fermentation broths of several different fungal strains and species were determined using this technique. The method was compared using ACV standards in buffer solutions for ease of use, sensitivity and selectivity with two other pre-column derivatisation procedures, using dithionitrobenzoic acid and monobromobimane, which also exploit the reaction with the sulphydryl group of the ACV monomer.

Acremonium↗
PubMed2002

Enantiomeric separations using poly(L-valine) and poly(L-leucine) surfactants. Investigation of steric factors near the chiral center.

This study examined the effect of steric factors near the stereogenic center on polymerized surfactants, sodium N-undecyl-L-leucine, sodium N-undecyl-L-norleucine, sodium N-undecyl-L-tert.-butyl leucine, sodium N-undecyl-L-isoleucine. sodium N-undecyl-L-valine, sodium N-undecyl-L-norvaline. and sodium N-undecyl-L-proline. The effect of steric factors near the chiral center of the polymeric surfactants were examined using binaphthyl derivatives, aminoglutethimide, and 2,2,2-trifluoro-1-(9-anthryl)ethanol. In addition, fluorescence spectroscopy was used to determine the hydrophobicities of these surfactants using the environmentally-sensitive probe pyrene.

Hydrogen Bonding↗
PubMed2000

Effect of leucinyl-phenylalanyl-valine on DMPC liposome membrane.

Leucinyl-phenylalanyl-valine (LFV) is a hydrophobic tripeptide with a flat egg shaped structure with the long axis dimension of about 12 A. The effect of LFV on dimyristoylphosphatidylcholine (DMPC) liposome membrane has been studied by differential scanning calorimetry (DSC) and fluorescence spectroscopy. Calorimetric studies shows that incorporation of LFV completely abolishes the pretransition temperature with broadening of main transition temperature. Four conceptually different fluorescence probes, 1-naphthol (1-ROH) an excited state proton transfer probe, 8-anilino-1-naphthalenesulphonate (ANS) a solvent polarity probe, 1-6-diphenylhexatriene (DPH) an anisotropy probe and pyrene an excimer-forming probe have been used for fluorescence spectroscopic studies. For 1-ROH, ANS and DPH, a decreased partitioning with increasing mol.% of LFV was observed. Increasing LFV mol.% caused a decrease in the neutral form emission of 1-ROH, and a decrease in fluorescence intensity with red shift in ANS. The excimer formation ability of pyrene also decreased. The phase transition behavior of DMPC membrane in the presence of LFV was similar to the known effect of cholesterol on lipid bilayers. These results suggest that LFV cause an increased compactness of membrane.

Calorimetry, Differential Scanning↗
PubMed2003

Photoacoustic spectroscopy study of neodymium complexes with alanine, valine, phenylalanine and tryptophan.

Neodymium complexes with amino acids: Nd(Ala)(3)Cl(3).3H(2)O, Nd(Val)(3)Cl(3).3H(2)O, Nd(Phe)Cl(3).5H(2)O and Nd(Trp)(3)Cl(3).3H(2)O (Ala: L-alanine, Val: L-valine, Phe: L-phenylalanine, Trp: L-tryptophan) are synthesized and their photoacoustic (PA) spectra are reported. The nephelauxetic ratio beta, bonding parameter b(1/2) and Sinha parameter delta are calculated based on their PA spectra. The variation of these parameters and correlation of them with the nature of metal-ligand bonding are discussed. The PA intensity analysis of the f-f transitions of neodymium ion is carried out by calculating the intensity branching vector. The environmental effect on the f-f transitions of neodymium ion is also studied. The branching vectors of the f-f transitions of Nd(Ala)(3)Cl(3).3H(2)O and Nd(Val)(3)Cl(3).3H(2)O are similar, which indicates the perturbation of the two ligand fields is similar. The branching vectors of energy levels 4G(5/2)+(2)G(7/2) of Nd(Phe)Cl(3).5H(2)O and Nd(Trp)(3)Cl(3).3H(2)O increase remarkably compared with those of Nd(Ala)(3)Cl(3).3H(2)O and Nd(Val)(3)Cl(3).3H(2)O. As the degree of covalency increases, the oscillator strength of the hypersensitive transition exhibits a corresponding increase. The relaxation process of Nd(Ala)(3)Cl(3).3H(2)O is established through its PA and electron absorption spectroscopy (EAS). A method used to resolve the PA amplitude spectrum is suggested. With the phase spectrum, PA absorption bands of Nd(Trp)(3)Cl(3).3H(2)O are resolved well in the region of ligand absorption.

Absorption↗
PubMed2003

The development of inversion in wh-questions: a reply to Van Valin.

Van Valin (Journal of Child Language 29, 2002, 161-75) presents a critique of Rowland & Pine (Journal of Child Language 27, 2000, 157-81) and argues that the wh-question data from Adam (in Brown, A first language, Cambridge, MA, 1973) cannot be explained in terms of input frequencies as we suggest. Instead, he suggests that the data can be more successfully accounted for in terms of Role and Reference Grammar. In this note we re-examine the pattern of inversion and uninversion in Adam's wh-questions and argue that the RRG explanation cannot account for some of the developmental facts it was designed to explain.

Child Language↗
PubMed1982

Leukocyte valine dehydrogenase activity in Friedreich's ataxia.

We studied the activity of valine dehydrogenase (VDH) in leukocytes of 14 Friedreich's ataxia patients and of 14 normal control subjects. There was a significant 26% mean decrease in enzyme activity in the patients, a finding which could be responsible for the chronic accumulation of some alpha-keto acids with toxic metabolic consequences in that disease. However the deficiency was not present in all patients with the typical symptoms, nor was its magnitude sufficient to be considered the primary genetic defect in Friedreich's Ataxia.

Adult↗
PubMed1997

Studies of polymerized sodium N-undecylenyl-L-valinate in chiral micellar electrokinetic capillary chromatography of neutral, acidic, and basic compounds.

The polymerized surfactant poly(sodium N-undecylenyl amino L-valinate) [poly(L-SUV)] has been used in micellar electrokinetic capillary chromatography for the chiral separation of various acidic and basic drugs, as well as neutral compounds. Under the conditions studied, poly(L-SUV) was shown to be a very versatile anionic chiral selector in the pH range of 5.6-11. The micelle was used for the enantioseparation of coumarinic anticoagulant drugs with various buffers under moderately acidic conditions. Neutral and alkaline buffer conditions were used to successfully separate the neutral atropisomers (+/-)-1,1'-bi-2-naphthol, (+/-)-1,1'-binaphthyl-2,2'-diamine, and Tröger's base. Chiral separation of the cationic paveroline drugs, laudanosine, norlaudanosoline, and laudanosoline, was influenced by pH and the use of coated capillaries. The acquired data focused on optimizing the migration times, capacity and separation factors, and electrophoretic mobilities of the various racemic mixtures.

Chromatography↗
PubMed1987

Mechanism for slow-binding inhibition of human leukocyte elastase by valine-derived benzoxazinones.

Valine-derived benzoxazinones have been synthesized and found to be competitive, slow-binding inhibitors of human leukocyte elastase (HLE). Steady-state inhibition constants Ki are dependent on aryl substitution and reach a maximum of potency of 0.5 nM with the 5-Cl compound 6. UV-spectral data for the interaction of HLE and the unsubstituted inhibitor 3 indicate that the stable complex formed between enzyme and inhibitor is an acyl-enzyme that can either undergo ring closure, to reform intact benzoxazinone, or hydrolysis, to liberate an N-acylanthranilic acid. "Burst" kinetic data, derived from the direct observation of the interaction of HLE and 3, are consistent with results of the inhibition of catalysis experiments.

Acylation↗
PubMed1981

Optically detected magnetic resonance of the phosphorescent bases of Escherichia coli valine-specific transfer ribonucleic acid.

Phosphorescence spectroscopy and optical detection of triplet state magnetic resonance (ODMR) spectroscopy have been used to characterize bases that contribute to the phosphorescence emission of Escherichia coli valine-specific transfer ribonucleic acid. When it is excited with 335-nm light, a short-lived phosphorescence with an origin near 435 nm is observed and is assigned to 4-thiouridine (s4U) at position 8 of the tRNA sequence. With excitation at 290-300 nm, a structured, long-lived phosphorescence is observed with an origin near 380 nm, in addition to the s4U phosphorescence. Comparison was made of the phosphorescence and ODMR spectra between Mg2+-containing and Mg2+-free tRNA samples. The s4U phosphorescence of the Mg2+-containing sample is more structured, and the peak is blue shifted relative to the Mg2+-free sample. Both samples give a single low-frequency (ca. 2.9 GHz) ODMR signal, but the high-frequency signal region (ca. 19-20 GHz) is structured. The Mg2+-containing sample has a partially resolved group of lines centered at 19.3 GHz, whereas the Mg2+-free sample has two broad bands centered at 19.2 and 20.0 gHz. The differences are attributed to effects of Mg2+ on the tRNA conformation. The ODMR signals observed by monitoring the long-lived phosphorescence are assigned to a pyrimidine nucleoside, possibly 5-(carboxy-methoxy)uridine in the anticodon.

Base Sequence↗
PubMed1997

Molybdenum(VI) Peroxo alpha-Amino Acid Complexes: Synthesis, Spectra, and Properties of MoO(O(2))(2)(alpha-aa)(H(2)O) for alpha-aa = Glycine, Alanine, Proline, Valine, Leucine, Serine, Asparagine, Glutamine, and Glutamic Acid. X-ray Crystal Structures of the Glycine, Alanine, and Proline Compounds.

The compounds MoO(O(2))(2)(alpha-aa)(H(2)O), alpha-aa = glycine (1), alanine (2), proline (3), valine (4), leucine (5), serine (6), asparagine (7), glutamine (8), and glutamic acid (9), were prepared from the acidic aqueous solutions and characterized by examination of their IR, (1)H and (13)C NMR, and UV-visible spectra. They represent the first complexes containing a peroxo-alpha-amino acid combination in a metal ion ligand sphere. The synthesis and crystallization of these complexes was pH and concentration dependent, and their stability varied for different alpha-amino acids. X-ray structural studies of 1-3 have shown that the alpha-amino acids are coordinated as a zwitterion via one oxygen. This oxygen of the monodentate carboxylato group occupies an equatorial position in a distorted pentagonal bipyramid and encloses the pentagonal ring with the two bidentate peroxo groups. The apical positions are occupied by an oxo group and a water molecule, respectively. The Mo-O(O(2)) bonds are nonsymmetrical, differing in length by 0.009-0.045 Å. The longer bonds are located next to the coordinated carboxylato oxygen. A correlation between O-O and Mo-O bond lengths with the IR and UV-visible spectra of complexes 1-3 is discussed. Crystal structure of MoO(O(2))(2)(alanine)(H(2)O): monoclinic, space group P2(1)/c; Z = 4; a = 10.727(3) Å; b = 8.026(2) Å; c = 10.794(4) Å; beta = 110.81(2) degrees; V = 869 (Å)(3); R = 0.041. (1)H and (13)C NMR spectra in D(2)O solutions showed the presence of one complex species, which decomposed by standing in solution. Analogies and differences between Mo(VI) and V(V) peroxo complexes are outlined.

Journal Article↗
PubMed1977

[1-(L-2-hydroxy-3-mercaptopropanoic acid)] analogues of arginine-vasopressin, [8-D-arginine]vasopressin, and [4-valine,8-D-arginine]vasopressin.

[1-(L-2-Hdroxy-3-mercaptopropanic acid)]arginine-vasopressin (hydroxy-AVP), [1-(L-2-hydroxy-3-mercaptopropanoic acid),8-D-arginine]vasopressin (hydroxy-DAVP), and [1-(L-2-hydroxy-3-mercaptopropanoic acid),4-valine,8-D-arginine]vasopressin (hydroxy-VDAVP) were synthesized by a combination of the solid-phase and solution methods of peptide synthesis. Protected octapeptides synthesized by the solid-phase method were further acylated by 1 + 8 couplings in solution to furnish the key intermediates. Hydroxy-AVP has antidiuretic potency of 470 units/mg and activity in the rat vasopressor assay of 550 units/mg, representing a small enhancement of activity over that of arginine-vasopressin (AVP) in each case. Hydroxy-DAVP and hydroxy-VDAVP have essentially the same high antidiuretic activity (900 units/mg) and very low vasopressor potencies (0.9 and less than 0.02 units/mg, respectively). Hydroxy-AVP, hydroxy-DAVP, and hydroxy-VDAVP thus have antidiuretic-pressor selectivity (A/P) of 1, 1000, and greater than 45 000, respectively. These data are compared with those of other vasopressin analogues. Hydroxy-VDAVP is a highly specific antidiuretic peptids and may be useful in pharmacological studies of antidiuresis.

Arginine Vasopressin↗