Some Reactions of δ-Aminovaleric Acid and its Derivatives

Schniepp, L. E.; Marvel, C. S.

doi:10.1021/ja01312a014

Cited by 12 publications

(6 citation statements)

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“…Reaction (1) was carried out by the procedure describedbyBousquet (1943) forthesynthesis of heptaldoxime. Reactions (2) and (3) were carried out as described by Schniepp & Marvel (1935). All compounds were recrystallized twice before use, and were pure as judged by the melting point and one-dimensional paper chromatography in propanol-ammonia-water (60:30: 10).…”

Section: I957mentioning

confidence: 99%

The purification and properties of arginine phosphokinase

Morrison

Griffiths

Ennor

1957

Biochemical Journal

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FORMATION OF AMMONIA FROM GLUTAMINE 143 presence of IMP and CP resulted in about 97 % inhibition of production of ammonia. This result would be expected if the enzyme responsible were the brain glutaminase described by Krebs (1935). With inorganic phosphate (5 or 10 tmoles/ml.) replacing the IMP and CP in the system, addition of glutamic acid (4 /Lmoles/ml.) was accompanied by a very marked decrease in production of ammonia. Greenstein & Leuthardt (1948) found that bicarbonate buffer did not activate glutaminase. Further evidence for this has been found in the low blank values. They measured the stimulatory effect of various ions on glutaminase, and some organic derivatives of phosphate and arsenate. The present study has included more multivalent ions, since Greenstein & Leuthardt (1948) had shown that univalent ions were poor stimulators ofthe reaction. It was concluded that, in general, as the ionic charge increased so did the effectiveness in stimulating production of ammonia (Table 5). The effect obtained by Weil-Malherbe (1953) can be readily explained on the basis of an anion activation of brain glutaminase by phosphate formed by hydrolysis during the incubation, or by phosphate and sulphate added initially in these solutions. SUMMARY 1. The formation of ammonia from glutamine by rat-brain particles in the presence of inosine triphosphate, or inosinic acid and creatine phosphate, is explained by the presence of low concentrations of phosphate and sulphate which activate the glutaminase present. 2. The reaction is 97 % inhibited by the addition of L-glutamic acid. 3. The effect of various other ions on the reaction was studied. The results indicated that, as the ionic charge increases, so does the efficacy in stimulating production of ammonia. 4. The synthesis of adenosine 5'-monophosphate from inosinic acid does not occur in this system under these conditions.

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Section: I957mentioning

confidence: 99%

The purification and properties of arginine phosphokinase

Morrison

Griffiths

Ennor

1957

Biochemical Journal

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“…Experimental procedures thought to be of special interest in connection with the authors' synthesis are (a) the use of hydroxylamine sulfate to convert cyclopentanone (I) to the corresponding oxime (II) in place of sodium nitrite and sodium bisulfite employed by Eck and Marvel (12) for the synthesis of cyclohexanone oxime and (b) the preparation of -benzoylamino-n-valeric acid (V) from cyclopentanone oxime (II) in about 71% over-all yield. According to Schniepp and Marvel (13) the over-all yield is only 29% of the theoretical amount when the intermediate substances (III) and (IV) are isolated. d,Z-Ornithine monohydrochloride may be prepared by the described method somewhat more conveniently than from -phthalimidopropylmalonic ester (14), /3-vinylacrylic acid (15), -phthalimidopropylthalimidomalonic ester (16), piperidine (17), acrolein (18), or -aminoadipic acid and hydrazoic acid (19).…”

Section: D Z-citrullinementioning

confidence: 98%

“…The hydroxylamine sulfate was obtained from the Commercial Solvents Co., Terre Haute,Indiana. 4 This synthesis is a modification of the procedures reported by Schniepp and Marvel(13),Fischer and Zemplén (17),and Maeda and Nozoe (20) 5. According to Schotten (24) and Gabriel(25) the melting point of -benzoylaminon-valeric acid is 94°.…”

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THE SYNTHESIS OF d,l-CITRULLINE FROM NON-BIOLOGICAL PRECURSORS¹

Fox¹,

Dunn²,

Stoddard³

1941

J. Org. Chem.

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“…Schniepp and Marvel(273) employed a somewhat similar method for preparing ornithine and arginine, starting with cyclopentanone through the oxime. )4COOH-> etc.…”

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confidence: 99%

“…used a combination of Marvel's(101,273) cyclopentanone method and Fischer's method(130) to prepare proline. 277) used double decomposition of p-toluenesulfonamide and -halogen acids for the preparation of amino acids.…”

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confidence: 99%

The Isolation and Synthesis of the Naturally Occurring a-Amino Acids.

Block¹

1946

Chem. Rev.

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Some Reactions of δ-Aminovaleric Acid and its Derivatives

Cited by 12 publications

References 0 publications

The purification and properties of arginine phosphokinase

The purification and properties of arginine phosphokinase

THE SYNTHESIS OF d,l-CITRULLINE FROM NON-BIOLOGICAL PRECURSORS¹

The Isolation and Synthesis of the Naturally Occurring a-Amino Acids.

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Some Reactions of δ-Aminovaleric Acid and its Derivatives

Cited by 12 publications

References 0 publications

The purification and properties of arginine phosphokinase

The purification and properties of arginine phosphokinase

THE SYNTHESIS OF d,l-CITRULLINE FROM NON-BIOLOGICAL PRECURSORS1

The Isolation and Synthesis of the Naturally Occurring a-Amino Acids.

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THE SYNTHESIS OF d,l-CITRULLINE FROM NON-BIOLOGICAL PRECURSORS¹