The enzymatic resolution of aromatic amino acids

Sheardy, Riehard; Liotta, Louis J.; Steinhart, E.; Champion, R. L.; Rinker, James M.; Planutis, M.; Salinkas, J.; Boyer, Thomas D.; Carcanague, D.

doi:10.1021/ed063p646

Cited by 9 publications

(6 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to the importance of students' mastering stereochemical concepts and understanding how to obtain optically pure compounds, resolutions have become standard experiments in organic chemistry laboratory courses. Examples of resolutions seen in laboratory texts and the literature include the resolution of d,l-(α)-phenethylamine using tartaric acid as a resolving agent (3)(4)(5)(6)(7)(8)(9), the resolution of mandelic acid using (-)-ephedrine as a resolving agent (10), the resolution of d,l-histidine using tartaric acid as the resolving agent (11), and the resolution of various amino acids by enzymatic resolution (12)(13)(14).…”

mentioning

confidence: 99%

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

McCullagh¹

2008

J. Chem. Educ.

View full text Add to dashboard Cite

In this experiment the over-the-counter pain reliever ibuprofen is resolved using (S)-(-)-α-phenethylamine as the resolving agent. This procedure has several key advantages over previous resolution experiments. First, it involves the resolution of a well-known medicinal compound of commercial importance. Second, the resolution process is simpler and more foolproof than previous experiments. Third, the product obtained at the end of the resolution process is chemically stable. Finally, the reagents used in this resolution are relatively inexpensive and easily obtained.

show abstract

mentioning

confidence: 99%

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

McCullagh¹

2008

J. Chem. Educ.

View full text Add to dashboard Cite

show abstract

“…α-Chymotrypsin, a protease with esterase activity, is often used for this purpose, since it is readily available. This enzyme preferably converts aromatic amino acid esters, as was demonstrated by the early successful resolutions of 2-, 3-, and 4-fluorophenylalanine [50,51]. A lower hydrolysis rate is observed for the α-chymotrypsin-catalyzed resolution of C α,α -dialkylated amino acids, in general and α-methyl-4-fluorophenylalanine, in particular [52].…”

Section: Resolution Using Esterase or Acylase Catalysismentioning

confidence: 94%

How Cα-Fluoroalkyl Amino Acids and Peptides Interact with Enzymes:Studies Concerning the Influence on Proteolytic Stability, Enzymatic Resolution and Peptide Coupling

Smits¹,

Koksch

2006

CTMC

View full text Add to dashboard Cite

Combination of the unique physical and chemical properties of fluorine with proteinogenic amino acids represents a new approach for the design of biologically active peptides with improved pharmacological parameters that carry a powerful label for spectroscopic analysis. However, the general consequences of amino acid fluorination on structure and activity of peptides and proteins are still controversially discussed. Studying the interaction of fluorinated amino acids with enzyme active sites provides valuable information on how fluoroalkyl groups of peptide-based drugs might interact with target proteins or receptors. Therefore, different enzymatic approaches including proteolysis studies, enzymatic resolutions and peptide bond couplings were studied by our group.

show abstract

“…The present type of hydrolysis has developed, beyond the production of (S )-valine, to a general procedure for obtaining the enantiomers of amino acids (24, 26a), some of which are required as food supplements for cattle. Such processes play a role for the preparation of many nonracemic organic compounds (2h, 27,28), several examples even being adapted for use in the teaching laboratory (29)(30)(31)(32)(33).…”

Section: Reactivities Of Enantiomers In Enzymatic Resolutionmentioning

confidence: 99%

Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands

Mannschreck

Kiesswetter

2005

J. Chem. Educ.

View full text Add to dashboard Cite

The intermolecular interactions of one enantiomer with a chiral auxiliary molecule and the interactions of the other enantiomer with the auxiliary are considered. Different functions of the latter give rise to the following well-known aspects of organic stereochemistry that are characterized in the present article: (i) preparative separation of enantiomers via crystallization of diastereomeric salts; (ii) analysis of enantiomers by NMR spectroscopy; (iii) separation of enantiomers by chromatography; (iv) biological activities of enantiomers; and (v) reactivities of enantiomers in enzymatic resolution. The common basis of these aspects is the formation of two diastereomeric association complexes that may differ with respect to their physical and chemical properties. The following practical applications of this phenomenon are briefly described: the small- and large-scale preparation of the enantiomers of organic compounds; the analysis of chiral nonracemic mixtures by chromatography and by NMR spectroscopy; and the growing use of drugs in the form of one of the enantiomers. It is proposed to emphasize the similarity of the association-based differentiations. This goal can be attained by giving a corresponding lecture in the second or third year of university chemistry.

show abstract

The enzymatic resolution of aromatic amino acids

Cited by 9 publications

References 3 publications

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

How Cα-Fluoroalkyl Amino Acids and Peptides Interact with Enzymes:Studies Concerning the Influence on Proteolytic Stability, Enzymatic Resolution and Peptide Coupling

Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands

Contact Info

Product

Resources

About

The enzymatic resolution of aromatic amino acids

Cited by 9 publications

References 3 publications

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

The Resolution of Ibuprofen, 2-(4'-Isobutylphenyl)propionic Acid

How C&#945;-Fluoroalkyl Amino Acids and Peptides Interact with Enzymes:Studies Concerning the Influence on Proteolytic Stability, Enzymatic Resolution and Peptide Coupling

Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands

Contact Info

Product

Resources

About

How Cα-Fluoroalkyl Amino Acids and Peptides Interact with Enzymes:Studies Concerning the Influence on Proteolytic Stability, Enzymatic Resolution and Peptide Coupling