Microbial degradation of 2,5-diketopiperazines

Hiroshi Kanzaki, Kazuyoshi Kawazu

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Enrichment culture of soil samples with cyclo(Gly-Gly) and cyclo(Gly-l-Tyr) as a carbon and/or a nitrogen source resulted in the isolation of Arthrobacter sp. 1-3-1 and the coryneform rod bacterium, strain T-1-3-Y, as the bacteria which most highly assimilated cyclo(Gly-Gly) and cyclo(Gly-l-Tyr), respectively. Both bacteria had the enzyme activity hydrolyzing DKPs intracellularly in contrast to the extracellular cyclo(Gly-Gly) hydrolase reported previously. The cells of Arthrobacter sp. 1-3-1 degraded all diketopiperazines tested, including cyclo(Gly-Gly), cyclo(Gly-l-Ala), cyclo(Gly-l-Val), cyclo(Gly-l-Leu), cyclo(Gly-l-Ile), cyclo(Gly-l-Met), cyclo(Gly-l-Phe), cyclo(Gly-l-Tyr), cyclo(l-Ala-l-Tyr), cyclo(l-Val-l-Tyr), cyclo(l-Leu-l-Tyr), cyclo(l-Tyr-l-Tyr), cyclo(l-Phe-l-Leu), cyclo(Gly-d-Ala), and cyclo(Gly-d-Leu). On the other hand, the degradation of d-amino acid-containing DKPs or cyclo(Gly-Gly) by the cells of the strain T-1-3-Y were detected hardly or not at all, respectively. From the result that DKP hydrolase in the strain T-1-3-Y had a higher stereospecificity than that in Arthrobacter sp. 1-3-1, the diversity of DKP hydrolases were found to be in nature.

Original languageEnglish
Pages (from-to)167-171
Number of pages5
JournalStudies in Organic Chemistry
Volume53
Issue numberC
DOIs
Publication statusPublished - 1998

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Diketopiperazines
Degradation
Hydrolases
Bacteria
2,5-dioxopiperazine
Enzyme activity
Nitrogen
Carbon
Soils
Amino Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Microbial degradation of 2,5-diketopiperazines. / Kanzaki, Hiroshi; Kawazu, Kazuyoshi.

In: Studies in Organic Chemistry, Vol. 53, No. C, 1998, p. 167-171.

Research output: Contribution to journalArticle

Kanzaki, Hiroshi ; Kawazu, Kazuyoshi. / Microbial degradation of 2,5-diketopiperazines. In: Studies in Organic Chemistry. 1998 ; Vol. 53, No. C. pp. 167-171.
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abstract = "Enrichment culture of soil samples with cyclo(Gly-Gly) and cyclo(Gly-l-Tyr) as a carbon and/or a nitrogen source resulted in the isolation of Arthrobacter sp. 1-3-1 and the coryneform rod bacterium, strain T-1-3-Y, as the bacteria which most highly assimilated cyclo(Gly-Gly) and cyclo(Gly-l-Tyr), respectively. Both bacteria had the enzyme activity hydrolyzing DKPs intracellularly in contrast to the extracellular cyclo(Gly-Gly) hydrolase reported previously. The cells of Arthrobacter sp. 1-3-1 degraded all diketopiperazines tested, including cyclo(Gly-Gly), cyclo(Gly-l-Ala), cyclo(Gly-l-Val), cyclo(Gly-l-Leu), cyclo(Gly-l-Ile), cyclo(Gly-l-Met), cyclo(Gly-l-Phe), cyclo(Gly-l-Tyr), cyclo(l-Ala-l-Tyr), cyclo(l-Val-l-Tyr), cyclo(l-Leu-l-Tyr), cyclo(l-Tyr-l-Tyr), cyclo(l-Phe-l-Leu), cyclo(Gly-d-Ala), and cyclo(Gly-d-Leu). On the other hand, the degradation of d-amino acid-containing DKPs or cyclo(Gly-Gly) by the cells of the strain T-1-3-Y were detected hardly or not at all, respectively. From the result that DKP hydrolase in the strain T-1-3-Y had a higher stereospecificity than that in Arthrobacter sp. 1-3-1, the diversity of DKP hydrolases were found to be in nature.",
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