Erlenmeyer–Plöchl azlactone and amino-acid synthesis

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The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after

azlactone).[1][2]

Azlactone chemistry: step 2 is a Perkin variation
Azlactone chemistry: step 2 is a Perkin variation

azlactone. This compound on reduction gives access to phenylalanine.[4]

Variations

Variants of the azlactone synthesis in which analogues of azlactones are used are sometimes advantageous. Hydantoin (in Bergmann modification), thiohydantoin and rhodanine have each been employed as the enolate-forming component of the condensation. [5][6] 2,5-Diketopiperazine can be used as a methylene component as well; its condensation products with aromatic aldehydes, on reduction and hydrolysis give the corresponding amino acids. [7][8][9]

Scope

In one study the Erlenmeyer amino acid synthesis was used in the heart of an

L-m-tyrosine synthesis [10][11]

ErlenMeyer Amino Acid Synthesis Tyrosine

See also

References

  1. doi:10.1002/cber.18840170215
    . ; see especially pp. 1623-1624.
  2. doi:10.1002/jlac.18932750102
    . ; see especially pp. 3-8.
  3. ^ G. E. VandenBerg, J. B. Harrison, H. E. Carter, B. J. Magerlein (1973). "2-Phenyl-2-oxazolone". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 5, p. 946.
  4. ^ H. B. Gillespie, H. R. Snyder (1934). "dl-β-Phenylalanine". Organic Syntheses; Collected Volumes, vol. 2, p. 489.
  5. ISBN 9780080966304
    .
  6. ISBN 9780748761623
    .
  7. ^ H.D. Dakin. Aromatic aldehyde derivatives of proteins, peptides and amino acids. J. Biol. Chem. 1929, 84:675-682
  8. ^ Alan D. Borthwick. 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products. DrugMolDesign, 15 Temple Grove, London NW11 7UA, U.K. Chem. Rev., 2012, 112 (7), pp 3641–3716. DOI: 10.1021/cr200398y
  9. ^ A. M. Asiri. New Conjugated Systems Derived from Piperazine-2,5-dione. Molecules 2000, 5, 629-636
  10. doi:10.1021/op700093y.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  11. racemic and kinetic resolution is brought about by an enzyme which is able to only cleave the methyl ester of the S-enantiomer (forming (S)-5 soluble in dichloromethane
    ) leaving water-soluble (R)-4 untouched. The final step is amide cleavage to (S)-L-m-tyrosine 6
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