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N-acylglycine amidation: implications for the biosynthesis of fatty acid primary amides

Academic Article
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Overview

related to degree

  • Patterson, Jean, Ph.D. in Chemistry, Scripps Research 1992 - 1997

authors

  • Wilcox, B. J.
  • Ritenour-Rodgers, K. J.
  • Asser, A. S.
  • Baumgart, L. E.
  • Baumgart, M. A.
  • Boger, Dale
  • DeBlassio, J. L.
  • deLong, M. A.
  • Glufke, U.
  • Henz, M. E.
  • King, L.
  • Merkler, K. A.
  • Patterson, Jean
  • Robleski, J. J.
  • Vederas, J. C.
  • Merkler, D. J.

publication date

  • March 1999

journal

  • Biochemistry  Journal

abstract

  • Bifunctional peptidylglycine alpha-amidating enzyme (alpha-AE) catalyzes the O2-dependent conversion of C-terminal glycine-extended prohormones to the active, C-terminal alpha-amidated peptide and glyoxylate. We show that alpha-AE will also catalyze the oxidative cleavage of N-acylglycines, from N-formylglycine to N-arachidonoylglycine. N-Formylglycine is the smallest amide substrate yet reported for alpha-AE. The (V/K)app for N-acylglycine amidation varies approximately 1000-fold, with the (V/K)app increasing as the acyl chain length increases. This effect is largely an effect on the KM,app; the KM,app for N-formylglycine is 23 +/- 0.88 mM, while the KM,app for N-lauroylglycine and longer chain N-acylglycines is in the range of 60-90 microM. For the amidation of N-acetylglycine, N-(tert-butoxycarbonyl)glycine, N-hexanoylglycine, and N-oleoylglycine, the rate of O2 consumption is faster than the rate of glyoxylate production. These results indicate that there must be the initial formation of an oxidized intermediate from the N-acylglycine before glyoxylate is produced. The intermediate is shown to be N-acyl-alpha-hydroxyglycine by two-dimensional 1H-13C heteronuclear multiple quantum coherence (HMQC) NMR.

subject areas

  • Adult
  • Amides
  • Animals
  • Catalysis
  • Enzyme Inhibitors
  • Fatty Acids
  • Female
  • Glycine
  • Glyoxylates
  • Humans
  • Kinetics
  • Mixed Function Oxygenases
  • Multienzyme Complexes
  • Oleic Acids
  • Rats
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Identity

International Standard Serial Number (ISSN)

  • 0006-2960

Digital Object Identifier (DOI)

  • 10.1021/bi982255j

PubMed ID

  • 10079066
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Additional Document Info

start page

  • 3235

end page

  • 3245

volume

  • 38

issue

  • 11

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