Discovery of arylmalonate decarboxylase and conversion of the function by rational design

Kenji Miyamoto, Hiromichi Ohta

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

Decarboxylation of malonic acid is a well-known process in the biosynthesis of long-chain fatty acids starting from acetic acid. If this kind of enzymes exhibits enantioselectivity for asubstituted malonates, it will be useful as a novel method for preparing optically active carboxylic acids. Indeed malonyl-CoA decarboxylase from uropygial gland is enantioselective to the substrate and the product. Racemate of methylmalonyl-CoA (1) was incubated with the above decarboxylase in 3H2O. (S)-Enantiomer was smoothly decarboxylated to result in 2-(3H)-propionyl-CoA (2), while (R)-isomer of the substrate remained intact (Equation 21.1). The absolute configuration of α-carbon of resulting 2 was revealed to be (R). Thus, the decarboxylase distinguishes the chirality of 1 and gives enantiomerically pure (R)-isomer by retention of configuration [1].

Original languageEnglish
Title of host publicationBiocatalysis in the Pharmaceutical and Biotechnology Industries
PublisherCRC Press
Pages547-561
Number of pages15
ISBN (Electronic)9781420019377
ISBN (Print)9780849337321
Publication statusPublished - 2006 Jan 1

Fingerprint

Carboxy-Lyases
malonyl-CoA decarboxylase
Isomers
Malonates
Decarboxylation
Enantiomers
Chirality
Enantioselectivity
Biosynthesis
Substrates
Carboxylic Acids
Carboxylic acids
Fatty acids
Acetic acid
Acetic Acid
Fatty Acids
Carbon
Enzymes
Acids
malonate decarboxylase

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)
  • Chemical Engineering(all)
  • Medicine(all)
  • Pharmacology, Toxicology and Pharmaceutics(all)

Cite this

Miyamoto, K., & Ohta, H. (2006). Discovery of arylmalonate decarboxylase and conversion of the function by rational design. In Biocatalysis in the Pharmaceutical and Biotechnology Industries (pp. 547-561). CRC Press.

Discovery of arylmalonate decarboxylase and conversion of the function by rational design. / Miyamoto, Kenji; Ohta, Hiromichi.

Biocatalysis in the Pharmaceutical and Biotechnology Industries. CRC Press, 2006. p. 547-561.

Research output: Chapter in Book/Report/Conference proceedingChapter

Miyamoto, K & Ohta, H 2006, Discovery of arylmalonate decarboxylase and conversion of the function by rational design. in Biocatalysis in the Pharmaceutical and Biotechnology Industries. CRC Press, pp. 547-561.
Miyamoto K, Ohta H. Discovery of arylmalonate decarboxylase and conversion of the function by rational design. In Biocatalysis in the Pharmaceutical and Biotechnology Industries. CRC Press. 2006. p. 547-561
Miyamoto, Kenji ; Ohta, Hiromichi. / Discovery of arylmalonate decarboxylase and conversion of the function by rational design. Biocatalysis in the Pharmaceutical and Biotechnology Industries. CRC Press, 2006. pp. 547-561
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