Skip to main content
Applied and Environmental Microbiology logoLink to Applied and Environmental Microbiology
. 1997 Sep;63(9):3390–3393. doi: 10.1128/aem.63.9.3390-3393.1997

Formation of a Chiral Hydroxamic Acid with an Amidase from Rhodococcus erythropolis MP50 and Subsequent Chemical Lossen Rearrangement to a Chiral Amine

B Hirrlinger, A Stolz
PMCID: PMC1389238  PMID: 16535682

Abstract

The amidase from Rhodococcus erythropolis MP50 demonstrated, in the presence of hydroxylamine, acyltransferase activity and catalyzed the formation of hydroxamates from amides and hydroxylamine. The rates of acyltransferase activity of the purified amidase for the substrates acetamide, phenylacetamide, and 2-phenylpropionamide were higher than the corresponding rates for the hydrolysis reactions. With the substrate 2-phenylpropionamide the hydrolysis reaction and the acyltransferase activity were highly enantioselective. The optically active 2-phenylpropionhydroxamate was converted by a chemical Lossen rearrangement in an aqueous medium into the enantiopure S-1-phenylethylamine.

Full Text

The Full Text of this article is available as a PDF (191.3 KB).

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BRAMMAR W. J., CLARKE P. H. INDUCTION AND REPRESSION OF PSEUDOMONAS AERUGINOSA AMIDASE. J Gen Microbiol. 1964 Dec;37:307–319. doi: 10.1099/00221287-37-3-307. [DOI] [PubMed] [Google Scholar]
  2. Ciskanik L. M., Wilczek J. M., Fallon R. D. Purification and Characterization of an Enantioselective Amidase from Pseudomonas chlororaphis B23. Appl Environ Microbiol. 1995 Mar;61(3):998–1003. doi: 10.1128/aem.61.3.998-1003.1995. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Hirrlinger B., Stolz A., Knackmuss H. J. Purification and properties of an amidase from Rhodococcus erythropolis MP50 which enantioselectively hydrolyzes 2-arylpropionamides. J Bacteriol. 1996 Jun;178(12):3501–3507. doi: 10.1128/jb.178.12.3501-3507.1996. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Hoare D. G., Olson A., Koshland D. E., Jr The reaction of hydroxamic acids with water-soluble carbodiimides. A Lossen rearrangement. J Am Chem Soc. 1968 Mar 13;90(6):1638–1643. doi: 10.1021/ja01008a040. [DOI] [PubMed] [Google Scholar]
  5. Kobayashi M., Komeda H., Nagasawa T., Nishiyama M., Horinouchi S., Beppu T., Yamada H., Shimizu S. Amidase coupled with low-molecular-mass nitrile hydratase from Rhodococcus rhodochrous J1. Sequencing and expression of the gene and purification and characterization of the gene product. Eur J Biochem. 1993 Oct 1;217(1):327–336. doi: 10.1111/j.1432-1033.1993.tb18250.x. [DOI] [PubMed] [Google Scholar]
  6. Layh N., Stolz A., Böhme J., Effenberger F., Knackmuss H. J. Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates. J Biotechnol. 1994 Mar 31;33(2):175–182. doi: 10.1016/0168-1656(94)90109-0. [DOI] [PubMed] [Google Scholar]

Articles from Applied and Environmental Microbiology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES