The Use of Amino Acid Oxidases for the Small-scale Preparation of the Optical Isomers of Amino Acids

Parikh, Jekishan R.; Greenstein, Jesse P.; Winitz, Milton; Birnbaum, Sanford M.

doi:10.1021/ja01537a052

Cited by 55 publications

(12 citation statements)

References 3 publications

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“…The volume of the supernatant was reduced to approximately 1 ml in vacuo, and the amino acid solution was applied as a streak to Whatman 3MM paper (46 by 46 cm) and developed with the solvent mixture (1-butanol-acetic acidwater, 12:3:5) for 16 h. The air-dried paper was subjected to autoradiography; two bands were visible on the X-ray film. Free L-alloisoleucine was eluted from lower band (Rf, 0.66) and N-acetyl-D-alloisoleucine was eluted from the higher band ( (23,25,30).…”

Section: Methodsmentioning

confidence: 99%

“…Determination of amino acids was accomplished with the Beckman Spinco automatic amino acid analyzer (model 120C) (38,39) or by a modification of the paper chromatographic procedure described by Naftalin (23,29). Optical configuration of amino acids was established with dialyzed prepa-226 YAJIMA, MASON, AND KATZ rations of L-or 1-amino acid oxidase (23,25,30). Radioactive assays were conducted by the method of Katz and Weissbach (23).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Biogenetic Origin of the d -Isoleucine and N -Methyl- l -Alloisoleucine Residues in the Actinomycins

Yajima

Mason

Katz

1976

Antimicrob Agents Chemother

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Studies with 14 C-labeled isoleucine stereisomers have established that l -alloisoleucine, d -alloisoleucine, and d -isoleucine may function as precursors for the biogenesis of d -isoleucine and N -methyl- l -alloisoleucine residues in actinomycin. l -[ 14 C]isoleucine appears to be employed chiefly for d -alloisoleucine (and N -methylisoleucine [?] formation); however, its role in the biosynthesis of d -isoleucine and N -methylalloisoleucine remains unclear. The potential pathway of biosynthesis of d -isoleucine and N -methyl- l -isoleucine is discussed.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Biogenetic Origin of the d -Isoleucine and N -Methyl- l -Alloisoleucine Residues in the Actinomycins

Yajima

Mason

Katz

1976

Antimicrob Agents Chemother

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“…W was calculated from weight data, C from eq. [3], and [a] from eq. [4] (see below), using appropriate input data.…”

Section: Calculation Methods and Equationsmentioning

confidence: 99%

“…[2] from the density of the solution at the highest W value studied, and checked by appropriate measurements at a lower W value to make sure that it was constant, within experimental error, at differing concentrations. Equation [3] was derived from eqs.…”

Section: Concentrationsmentioning

confidence: 99%

Method for the accurate determination of specific rotation. Specific rotation of valine and leucine

MacDonald¹

1969

Can. J. Chem.

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The optical rotation of various concentrations of L-valine and L-leucine, dissolved in glacial acetic acid, or 5 or 6 M HC1, was measured with a photoelectric polarimeter at the nominal wavelengths 589, 578, 546,436, and 365 nm and temperatures of 20,25, and 30 "C. The specific rotation for any one wavelength, solute, and solvent could be defined by the equationwhere Tis temperature in "C, Cis concentration in grams of solute per 100 ml of solution, and A, B, and D are constants. The best fit values of the constants were determined by computer calculation and are listed. Constants are also given for calculating a specific rotation based on grams of solute per 100 g of solution.Canadian Journal of Chemistry, 47, 2739 (1969) IntroductionHayashi and co-workers (1) investigated the specific rotation of amino acids at the sodium D spectral lines (589.3 nm), and the effect of the concentration of solute, molarity of the solvent (aqueous HCI), and temperature on the specific rotation. They found that the specific rotation of leucine and valine increased with increases in the molarity of the HCI and in the concentration of the amino acids. If this is true, few of the specific rotations found in the literature for either of these two compounds can be directly compared, for it is seldom that different workers have used the same temperature, and the same concentrations for HC1 and amino acid.In the work reported here, a formula is developed by which specific rotations of L-valine and L-leucine measured under different conditions can be compared. The solvents used were 5 and 6 M HCl, which are frequently employed in optical rotation measurements of amino acids, and glacial acetic acid, which is employed less frequently.

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“…The α-keto acid analogues of the naturally occurring amino acids are of major importance in intermediary metabolism, in the development of enzyme inhibitors and drugs, as model substrates of enzymes, and in other ways (Brodelius, 1978). Parikh et al, (1958) provided an early example of the use of enzymes to prepare enantiomerically pure amino acids by selective destruction of one enantiomer in a racemic mixture with D-or L-amino acid…”

Section: Introductionmentioning

confidence: 99%

Bioconversion of Amino Acids to α-Keto Acid by Geotrichum candidum Used for the Treatment of Chronic Kidney Disorders

Chauhan¹,

Vyas²,

Shah³

et al. 2017

Int.J.Curr.Microbiol.App.Sci

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The Use of Amino Acid Oxidases for the Small-scale Preparation of the Optical Isomers of Amino Acids

Cited by 55 publications

References 3 publications

Biogenetic Origin of the d -Isoleucine and N -Methyl- l -Alloisoleucine Residues in the Actinomycins

Biogenetic Origin of the d -Isoleucine and N -Methyl- l -Alloisoleucine Residues in the Actinomycins

Method for the accurate determination of specific rotation. Specific rotation of valine and leucine

Bioconversion of Amino Acids to α-Keto Acid by Geotrichum candidum Used for the Treatment of Chronic Kidney Disorders

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