Glucosinolate biosynthesis: Demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa

Kimberly L. Falk, Christine Vogel, Susanne Textor, Stefan Bartram, Alastair Hick, John A. Pickett, Jonathan Gershenzon

Research output: Contribution to journalArticle

Abstract

Glucosinolates are a group of sulfur-rich thioglucoside natural products common in the Brassicaceae and related plant families. The first phase in the formation of many glucosinolates involves the chain extension of the amino acid methionine. Additional methylene groups are inserted into the side chain of methionine by a three-step elongation cycle involving 2-oxo acid intermediates. This investigation demonstrated the first step of this chain elongation cycle in a partially-purified preparation from arugula (Eruca sativa). The 2-oxo acid derived from methionine, 4-methylthio-2-oxobutanoic acid, was shown to condense with acetyl-CoA to form 2-(2′-methylthioethyl)malate. The catalyst, designated as a 2-(ω-methylthioalkyl)malate synthase, belongs to a family of enzymes that mediate the condensation of acyl-CoAs with 2-oxo acids, including citrate synthase of the citric acid cycle, and 2-isopropylmalate synthase of leucine biosynthesis. The 2-(ω-methylthioalkyl)malate synthase studied here shares properties with other enzymes of this class, but appears chromatographically distinct and is found only in extracts of plant species producing glucosinolates from chain-elongated methionine derivatives. Although the principal glucosinolates of arugula are formed from methionine that has undergone two rounds of chain elongation to form dihomomethionine, studies with substrates and substrate analogs of different chain lengths showed that the isolated enzyme is responsible only for the condensation step of the first round of elongation.

Original languageEnglish (US)
Pages (from-to)1073-1084
Number of pages12
JournalPhytochemistry
Volume65
Issue number8
DOIs
StatePublished - Apr 2004

Fingerprint

Glucosinolates
Eruca vesicaria subsp. sativa
Biosynthesis
glucosinolates
Methionine
methionine
Elongation
Keto Acids
Demonstrations
biosynthesis
arugula
Malate Synthase
malate synthase
Enzymes
enzymes
acids
2-Isopropylmalate Synthase
Condensation
Thioglucosides
Brassicaceae

Keywords

  • Arugula
  • Biosynthesis
  • Brassicaceae
  • Chain elongation
  • Condensing enzyme
  • Eruca sativa
  • Glucosinolate
  • Methionine
  • Methylthioalkylmalate synthase

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Glucosinolate biosynthesis : Demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa. / Falk, Kimberly L.; Vogel, Christine; Textor, Susanne; Bartram, Stefan; Hick, Alastair; Pickett, John A.; Gershenzon, Jonathan.

In: Phytochemistry, Vol. 65, No. 8, 04.2004, p. 1073-1084.

Research output: Contribution to journalArticle

Falk, Kimberly L. ; Vogel, Christine ; Textor, Susanne ; Bartram, Stefan ; Hick, Alastair ; Pickett, John A. ; Gershenzon, Jonathan. / Glucosinolate biosynthesis : Demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa. In: Phytochemistry. 2004 ; Vol. 65, No. 8. pp. 1073-1084.
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