Philippe Bey - Academia.edu (original) (raw)

Papers by Philippe Bey

Research paper thumbnail of Enzyme-Activated Irreversible Inhibition of Bacterial and Plant Arginine Decarboxylase, by Either Substrate or Product Analogues

Birkhäuser Basel eBooks, 1987

A regiospecific guanidination of ornithine and put re seine analogues, inhibitors of ornithine de... more A regiospecific guanidination of ornithine and put re seine analogues, inhibitors of ornithine decarboxylase (ODC), afforded the corresponding arginine and agmatine analogues. These new compounds were found to be very potent time-dependent, irreversible inhibitors of arginine decarboxylase from E. coli and plants. The potential use of these compounds is discussed.

Research paper thumbnail of ChemInform Abstract: Oxidation of α-Hydroxy Esters to α-Keto Esters Using the Dess-Martin Periodinane Reagent

ChemInform, Dec 27, 1988

β‐Nitrostyrene (I) is hydrogenated and then coupled with the glyoxylic acid monohydrate (III) to ... more β‐Nitrostyrene (I) is hydrogenated and then coupled with the glyoxylic acid monohydrate (III) to produce the 2‐hydroxy‐3‐nitro‐4‐phenylbutyric acid (IV).

Research paper thumbnail of ChemInform Abstract: Synthesis and Inhibitory Properties of α(Chlorofluoromethyl)-α-amino Acids, a Novel Class of Irreversible Inactivators of Decarboxylases

ChemInform, Aug 21, 2010

Aminophenols Q 0220 Synthesis and Inhibitory Activity of Alkyl(hydroxyaryl)amines.-A variety of a... more Aminophenols Q 0220 Synthesis and Inhibitory Activity of Alkyl(hydroxyaryl)amines.-A variety of aminoalkylphenols are synthesized which exhibit a pronounced inhibition effect on the thermal oxidation of lard and hexadecane. They increase the thermooxidative stability of these substrates 3.4-30 times.

Research paper thumbnail of DL-α-Monofluoromethylputrescine is a potent irreversible inhibitor of Escherichia coli ornithine decarboxylase

Biochemical Journal, Jun 15, 1982

DL-a-Monofluoromethylputrescine (compound R.M.I. 71864) is an enzyme-activated irreversible inhib... more DL-a-Monofluoromethylputrescine (compound R.M.I. 71864) is an enzyme-activated irreversible inhibitor of the biosynthetic enzyme ornithine decarboxylase from Escherichia coli. This compound, however, has much less effect in vitro on ornithine decarboxylase obtained from Pseudomonas aeruginosa. These findings are in contrast with those previously found with the substrate analogue DL-a-difluoromethylornithine (compound R.M.I. 71782). The Ki of the DL-a-monofluoromethylputrescine for the E. coli ornithine decarboxylase is 1 10pM, and the half-life (t1) calculated for an infinite concentration of inhibitor is 2.1 min. When DL-a-monofluoromethylputrescine is used in combination with DL-a-difluoromethylarginine (R.M.I. 71897), an irreversible inhibitor of arginine decarboxylase, in vivo in E. coli, both decarboxylase activities are inhibited (>95%) but putrescine levels are only decreased to about one-third of control values and spermidine levels are slightly increased. an irreversible inhibitor of an ODC from Enterobacteria, but without effect on the enzyme from Pseudomonas aeruginosa. In the present study we report that DL-a-monofluoromethylputrescine is a potent irreversible inhibitor of ODC in E. coli but is much less effective in vitro on ODC activity of Pseudomonas aeruginosa.

Research paper thumbnail of Anti-proliferative properties of DL-α-difluoromethyl ornithine in cultured cells. A consequence of the irreversible inhibition of ornithine decarboxylase

Biochemical and Biophysical Research Communications, Mar 1, 1978

Abstract Both DL-α-Methyl orinithine (α-MeOrn), a competitive inhibitor of ornithine decarboxylas... more Abstract Both DL-α-Methyl orinithine (α-MeOrn), a competitive inhibitor of ornithine decarboxylase (ODC) (L-orinithine carboxy-lyase EC 4.1.1.17) and DL-α-difluoromethyl orinithine (α-DF MeOrn), a catalytic irreversible inhibitor of this enzyme, decrease the concentrations of putrescine and spermidine but not of spermine in rat hepatoma (HTC) cells and in mouse leukemia cells cultured in vitro . The depletion of the two amines is followed by a striking decrease in the rate of cell replication in both cell lines. Growth of human prostate adenoma cells is inhibited by α-DF MeOrn but not by α-MeOrn, illustrating the greater effectiveness of the irreversible inhibitor. These findings again support an essential function for putrescine and spermidine in cell division processes.

Research paper thumbnail of ChemInform Abstract: A Novel Method for the Preparation of Peptidyl α-Keto Esters

Research paper thumbnail of Mechanism of the irreversible inactivation of mouse ornithine decarboxylase by alpha-difluoromethylornithine. Characterization of sequences at the inhibitor and coenzyme binding sites

Journal of Biological Chemistry, 1992

Research paper thumbnail of ChemInform Abstract: ALKYLATION OF MALONATES OR SCHIFF BASE ANIONS WITH DICHLOROFLUOROMETHANE AS A ROUTE TO α-CHLOROFLUOROMETHYL OR α-FLUOROMETHYL α-AMINO ACIDS

Chemischer Informationsdienst, Apr 16, 1985

ChemInform Abstract Aus den Carbonsäurederivaten (I) entstehenüber die Salze (II) mit Fluordichlo... more ChemInform Abstract Aus den Carbonsäurederivaten (I) entstehenüber die Salze (II) mit Fluordichlormethan (III) die Substitutionsprodukte (IVa) und (IVb) sowie daraus die Amine (IVc), die zu (IVd) acyliert werden. Die Hydrolyse von (IVb) und (IVe) liefert die Aminoarbonsäurehydrochloride (V). Aus (IVa) und (IVd) entstehen die Reduktionsprodukte (VI), (VIb) wird zu (VII) verseift. Als Nebenprodukte bei der Umsetzung von (II) entstehen die Imine (VIII), die mit Salzsäure das Amin (IX) eliminieren. (IR-, NMR-Daten).

Research paper thumbnail of ChemInform Abstract: α-(FLUOROMETHYL)DEHYDROORNITHINE AND α-(FLUOROMETHYL)DEHYDROPUTRESCINE ANALOGS AS IRREVERSIBLE INHIBITORS OF ORNITHINE DECARBOXYLASE

Chemischer Informationsdienst, Apr 10, 1984

Auf den im Formelschema skizzierten Wegen werden die Dehydroanaloga (V), (VI), (XI) und (XII) der... more Auf den im Formelschema skizzierten Wegen werden die Dehydroanaloga (V), (VI), (XI) und (XII) der entsprechenden Ornithine bzw. Putrescine dargestellt.

Research paper thumbnail of ChemInform Abstract: GENERAL APPROACH TO THE SYNTHESIS OF α-DIFLUOROMETHYL AMINES AS POTENTIAL ENZYME-ACTIVATED IRREVERSIBLE INHIBITORS

Chemischer Informationsdienst, Apr 17, 1979

Research paper thumbnail of ChemInform Abstract: A GENERAL PREPARATION OF FLUOROALLYLAMINE ENZYME INHIBITORS INCORPORATING A β-SUBSTITUTED HETEROATOM

Chemischer Informationsdienst, Dec 17, 1985

Research paper thumbnail of ChemInform Abstract: An Efficient Synthesis of Novel α-Diketone and α-Keto Ester Derivatives of N-Protected Amino Acids and Peptides

Research paper thumbnail of ChemInform Abstract: N-(2,3-BUTADIENYL)-1,4-BUTANEDIAMINE DERIVATIVES: POTENT IRREVERSIBLE INACTIVATORS OF MAMMALIAN POLYAMINE OXIDASE

Chemischer Informationsdienst, May 28, 1985

Research paper thumbnail of DL-3,3-difluoroglutamate: an enhancer of folylpolyglutamate elongation

Journal of Biological Chemistry, Aug 1, 1990

This is an Open Access article under the CC BY license.

Research paper thumbnail of Synthesis and inhibitory properties of α(chlorofluoromethyl)-α-amino acids, a novel class of irreversible inactivators of decarboxylases

Journal of the Chemical Society, 1992

ABSTRACT The synthesis of α-(chlorofluoromethyl)-ornithine 7, -metatyrosine 8 and -glutamic acid ... more ABSTRACT The synthesis of α-(chlorofluoromethyl)-ornithine 7, -metatyrosine 8 and -glutamic acid 14 is described. Separation of diastereoisomers and relative configuration assignment by X-ray analysis are reported. Assignment of absolute configuration of the four enantiomers of α-(chlorofluoromethyl)-ornithine 7 is also described. The inhibitory properties against ornithine decarboxylase, aromatic amino acid decarboxylase and glutamate decarboxylase are reported in terms of diastereoselectivity (8 and 14) or enantioselectivity (7).

Research paper thumbnail of Enone-benzene rearrangement

Chemical & pharmaceutical bulletin, 1965

Research paper thumbnail of New approach to the synthesis of α-halogenomethyl-α-amino acids

Tetrahedron Letters, 1978

Research paper thumbnail of Synthesis of α-alkyl and α-functionalized methyl-α-amino acids

Tetrahedron Letters, 1977

Research paper thumbnail of ChemInform Abstract: STEREOSPECIFIC ALKYLATION OF THE SCHIFF BASE ESTER OF ALANINE WITH 2-SUBSTITUTED-(E)- AND -(Z)-VINYL BROMIDES. AN EFFICIENT SYNTHESIS OF 2-METHYL-(E)-3,4-DIDEHYDROGLUTAMIC ACID, A POTENT SUBSTRATE-INDUCED IRREVERSIBLE INHIBITOR OF L-G

Chemischer Informationsdienst, Dec 16, 1980

ChemInform Abstract Die Acetylene (I) reagieren mit Bis-(π-allyl)-nickel (II) stereospezifisch zu... more ChemInform Abstract Die Acetylene (I) reagieren mit Bis-(π-allyl)-nickel (II) stereospezifisch zu cis-diallyliertenÄthylenen (III) in Ausbeuten von 30-50%, während als Nebenprodukte monoallylierte Produkte und Propenylverbindungen (IV) bis (VI) sowie Produkte einer eduktiven Dimerisierung (VII) und Cyclotrimerisierung (VIII) gefunden werden. Die deuterolytische Aufarbeitung des Reaktionsgemisches ergibt aus einem als Zwischenstufe postulierten "Nickelol" (X) das Dideuterodien (XI).

Research paper thumbnail of ChemInform Abstract: SYNTHESIS OF α-ALKYL AND α-FUNCTIONALIZED METHYL-α-AMINO ACIDS

Chemischer Informationsdienst, Aug 9, 1977

ChemInform Abstract Aus den Aminosäuren (I) werden die Schiffschen Basen (II) hergestellt, die mi... more ChemInform Abstract Aus den Aminosäuren (I) werden die Schiffschen Basen (II) hergestellt, die mit Lithiumdiisopropylamid in Anionenübergeführt und zu (III) substituiert werden. Diese werden zu (IV) bzw. (V) verseift. In Tabellen werden zahlreiche Vertreter aufgeführt. Zu (III) führen neben Alkylierungsreaktionen auch Michael-Additionen.

Research paper thumbnail of Enzyme-Activated Irreversible Inhibition of Bacterial and Plant Arginine Decarboxylase, by Either Substrate or Product Analogues

Birkhäuser Basel eBooks, 1987

A regiospecific guanidination of ornithine and put re seine analogues, inhibitors of ornithine de... more A regiospecific guanidination of ornithine and put re seine analogues, inhibitors of ornithine decarboxylase (ODC), afforded the corresponding arginine and agmatine analogues. These new compounds were found to be very potent time-dependent, irreversible inhibitors of arginine decarboxylase from E. coli and plants. The potential use of these compounds is discussed.

Research paper thumbnail of ChemInform Abstract: Oxidation of α-Hydroxy Esters to α-Keto Esters Using the Dess-Martin Periodinane Reagent

ChemInform, Dec 27, 1988

β‐Nitrostyrene (I) is hydrogenated and then coupled with the glyoxylic acid monohydrate (III) to ... more β‐Nitrostyrene (I) is hydrogenated and then coupled with the glyoxylic acid monohydrate (III) to produce the 2‐hydroxy‐3‐nitro‐4‐phenylbutyric acid (IV).

Research paper thumbnail of ChemInform Abstract: Synthesis and Inhibitory Properties of α(Chlorofluoromethyl)-α-amino Acids, a Novel Class of Irreversible Inactivators of Decarboxylases

ChemInform, Aug 21, 2010

Aminophenols Q 0220 Synthesis and Inhibitory Activity of Alkyl(hydroxyaryl)amines.-A variety of a... more Aminophenols Q 0220 Synthesis and Inhibitory Activity of Alkyl(hydroxyaryl)amines.-A variety of aminoalkylphenols are synthesized which exhibit a pronounced inhibition effect on the thermal oxidation of lard and hexadecane. They increase the thermooxidative stability of these substrates 3.4-30 times.

Research paper thumbnail of DL-α-Monofluoromethylputrescine is a potent irreversible inhibitor of Escherichia coli ornithine decarboxylase

Biochemical Journal, Jun 15, 1982

DL-a-Monofluoromethylputrescine (compound R.M.I. 71864) is an enzyme-activated irreversible inhib... more DL-a-Monofluoromethylputrescine (compound R.M.I. 71864) is an enzyme-activated irreversible inhibitor of the biosynthetic enzyme ornithine decarboxylase from Escherichia coli. This compound, however, has much less effect in vitro on ornithine decarboxylase obtained from Pseudomonas aeruginosa. These findings are in contrast with those previously found with the substrate analogue DL-a-difluoromethylornithine (compound R.M.I. 71782). The Ki of the DL-a-monofluoromethylputrescine for the E. coli ornithine decarboxylase is 1 10pM, and the half-life (t1) calculated for an infinite concentration of inhibitor is 2.1 min. When DL-a-monofluoromethylputrescine is used in combination with DL-a-difluoromethylarginine (R.M.I. 71897), an irreversible inhibitor of arginine decarboxylase, in vivo in E. coli, both decarboxylase activities are inhibited (>95%) but putrescine levels are only decreased to about one-third of control values and spermidine levels are slightly increased. an irreversible inhibitor of an ODC from Enterobacteria, but without effect on the enzyme from Pseudomonas aeruginosa. In the present study we report that DL-a-monofluoromethylputrescine is a potent irreversible inhibitor of ODC in E. coli but is much less effective in vitro on ODC activity of Pseudomonas aeruginosa.

Research paper thumbnail of Anti-proliferative properties of DL-α-difluoromethyl ornithine in cultured cells. A consequence of the irreversible inhibition of ornithine decarboxylase

Biochemical and Biophysical Research Communications, Mar 1, 1978

Abstract Both DL-α-Methyl orinithine (α-MeOrn), a competitive inhibitor of ornithine decarboxylas... more Abstract Both DL-α-Methyl orinithine (α-MeOrn), a competitive inhibitor of ornithine decarboxylase (ODC) (L-orinithine carboxy-lyase EC 4.1.1.17) and DL-α-difluoromethyl orinithine (α-DF MeOrn), a catalytic irreversible inhibitor of this enzyme, decrease the concentrations of putrescine and spermidine but not of spermine in rat hepatoma (HTC) cells and in mouse leukemia cells cultured in vitro . The depletion of the two amines is followed by a striking decrease in the rate of cell replication in both cell lines. Growth of human prostate adenoma cells is inhibited by α-DF MeOrn but not by α-MeOrn, illustrating the greater effectiveness of the irreversible inhibitor. These findings again support an essential function for putrescine and spermidine in cell division processes.

Research paper thumbnail of ChemInform Abstract: A Novel Method for the Preparation of Peptidyl α-Keto Esters

Research paper thumbnail of Mechanism of the irreversible inactivation of mouse ornithine decarboxylase by alpha-difluoromethylornithine. Characterization of sequences at the inhibitor and coenzyme binding sites

Journal of Biological Chemistry, 1992

Research paper thumbnail of ChemInform Abstract: ALKYLATION OF MALONATES OR SCHIFF BASE ANIONS WITH DICHLOROFLUOROMETHANE AS A ROUTE TO α-CHLOROFLUOROMETHYL OR α-FLUOROMETHYL α-AMINO ACIDS

Chemischer Informationsdienst, Apr 16, 1985

ChemInform Abstract Aus den Carbonsäurederivaten (I) entstehenüber die Salze (II) mit Fluordichlo... more ChemInform Abstract Aus den Carbonsäurederivaten (I) entstehenüber die Salze (II) mit Fluordichlormethan (III) die Substitutionsprodukte (IVa) und (IVb) sowie daraus die Amine (IVc), die zu (IVd) acyliert werden. Die Hydrolyse von (IVb) und (IVe) liefert die Aminoarbonsäurehydrochloride (V). Aus (IVa) und (IVd) entstehen die Reduktionsprodukte (VI), (VIb) wird zu (VII) verseift. Als Nebenprodukte bei der Umsetzung von (II) entstehen die Imine (VIII), die mit Salzsäure das Amin (IX) eliminieren. (IR-, NMR-Daten).

Research paper thumbnail of ChemInform Abstract: α-(FLUOROMETHYL)DEHYDROORNITHINE AND α-(FLUOROMETHYL)DEHYDROPUTRESCINE ANALOGS AS IRREVERSIBLE INHIBITORS OF ORNITHINE DECARBOXYLASE

Chemischer Informationsdienst, Apr 10, 1984

Auf den im Formelschema skizzierten Wegen werden die Dehydroanaloga (V), (VI), (XI) und (XII) der... more Auf den im Formelschema skizzierten Wegen werden die Dehydroanaloga (V), (VI), (XI) und (XII) der entsprechenden Ornithine bzw. Putrescine dargestellt.

Research paper thumbnail of ChemInform Abstract: GENERAL APPROACH TO THE SYNTHESIS OF α-DIFLUOROMETHYL AMINES AS POTENTIAL ENZYME-ACTIVATED IRREVERSIBLE INHIBITORS

Chemischer Informationsdienst, Apr 17, 1979

Research paper thumbnail of ChemInform Abstract: A GENERAL PREPARATION OF FLUOROALLYLAMINE ENZYME INHIBITORS INCORPORATING A β-SUBSTITUTED HETEROATOM

Chemischer Informationsdienst, Dec 17, 1985

Research paper thumbnail of ChemInform Abstract: An Efficient Synthesis of Novel α-Diketone and α-Keto Ester Derivatives of N-Protected Amino Acids and Peptides

Research paper thumbnail of ChemInform Abstract: N-(2,3-BUTADIENYL)-1,4-BUTANEDIAMINE DERIVATIVES: POTENT IRREVERSIBLE INACTIVATORS OF MAMMALIAN POLYAMINE OXIDASE

Chemischer Informationsdienst, May 28, 1985

Research paper thumbnail of DL-3,3-difluoroglutamate: an enhancer of folylpolyglutamate elongation

Journal of Biological Chemistry, Aug 1, 1990

This is an Open Access article under the CC BY license.

Research paper thumbnail of Synthesis and inhibitory properties of α(chlorofluoromethyl)-α-amino acids, a novel class of irreversible inactivators of decarboxylases

Journal of the Chemical Society, 1992

ABSTRACT The synthesis of α-(chlorofluoromethyl)-ornithine 7, -metatyrosine 8 and -glutamic acid ... more ABSTRACT The synthesis of α-(chlorofluoromethyl)-ornithine 7, -metatyrosine 8 and -glutamic acid 14 is described. Separation of diastereoisomers and relative configuration assignment by X-ray analysis are reported. Assignment of absolute configuration of the four enantiomers of α-(chlorofluoromethyl)-ornithine 7 is also described. The inhibitory properties against ornithine decarboxylase, aromatic amino acid decarboxylase and glutamate decarboxylase are reported in terms of diastereoselectivity (8 and 14) or enantioselectivity (7).

Research paper thumbnail of Enone-benzene rearrangement

Chemical & pharmaceutical bulletin, 1965

Research paper thumbnail of New approach to the synthesis of α-halogenomethyl-α-amino acids

Tetrahedron Letters, 1978

Research paper thumbnail of Synthesis of α-alkyl and α-functionalized methyl-α-amino acids

Tetrahedron Letters, 1977

Research paper thumbnail of ChemInform Abstract: STEREOSPECIFIC ALKYLATION OF THE SCHIFF BASE ESTER OF ALANINE WITH 2-SUBSTITUTED-(E)- AND -(Z)-VINYL BROMIDES. AN EFFICIENT SYNTHESIS OF 2-METHYL-(E)-3,4-DIDEHYDROGLUTAMIC ACID, A POTENT SUBSTRATE-INDUCED IRREVERSIBLE INHIBITOR OF L-G

Chemischer Informationsdienst, Dec 16, 1980

ChemInform Abstract Die Acetylene (I) reagieren mit Bis-(π-allyl)-nickel (II) stereospezifisch zu... more ChemInform Abstract Die Acetylene (I) reagieren mit Bis-(π-allyl)-nickel (II) stereospezifisch zu cis-diallyliertenÄthylenen (III) in Ausbeuten von 30-50%, während als Nebenprodukte monoallylierte Produkte und Propenylverbindungen (IV) bis (VI) sowie Produkte einer eduktiven Dimerisierung (VII) und Cyclotrimerisierung (VIII) gefunden werden. Die deuterolytische Aufarbeitung des Reaktionsgemisches ergibt aus einem als Zwischenstufe postulierten "Nickelol" (X) das Dideuterodien (XI).

Research paper thumbnail of ChemInform Abstract: SYNTHESIS OF α-ALKYL AND α-FUNCTIONALIZED METHYL-α-AMINO ACIDS

Chemischer Informationsdienst, Aug 9, 1977

ChemInform Abstract Aus den Aminosäuren (I) werden die Schiffschen Basen (II) hergestellt, die mi... more ChemInform Abstract Aus den Aminosäuren (I) werden die Schiffschen Basen (II) hergestellt, die mit Lithiumdiisopropylamid in Anionenübergeführt und zu (III) substituiert werden. Diese werden zu (IV) bzw. (V) verseift. In Tabellen werden zahlreiche Vertreter aufgeführt. Zu (III) führen neben Alkylierungsreaktionen auch Michael-Additionen.