Investigating β-hydroxyenduracididine formation in the biosynthesis of the mannopeptimycins

Brad Haltli, Ying Tan, Nathan A. Magarvey, Melissa Wagenaar, Xihou Yin, Michael Greenstein, John A. Hucul, Mark Zabriskie

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The mannopeptimycins (MPPs) are potent glycopeptide antibiotics that contain both D and L forms of the unique, arginine-derived amino acid β-hydroxyenduracididine (βhEnd). The product of the mppO gene in the MPP biosynthetic cluster resembles several non-heme iron, α-ketoglutarate- dependent oxygenases, such as VioC and clavaminate synthase. The role of MppO in βhEnd biosynthesis was confirmed through inactivation of mppO, which yielded a strain that produced dideoxy-MPPs, indicating that mppO is essential for generating the β-hydroxy functionality for both βhEnd residues. Characterization in vitro of recombinant His 6-MppO expressed in E. coli revealed that MppO selectively hydroxylates the β carbon of free L-enduracididine.

Original languageEnglish (US)
Pages (from-to)1163-1168
Number of pages6
JournalChemistry and Biology
Volume12
Issue number11
DOIs
StatePublished - Nov 2005
Externally publishedYes

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His-His-His-His-His-His
Biosynthesis
L Forms
Oxygenases
Escherichia coli
Arginine
Carbon
Iron
Genes
Anti-Bacterial Agents
Amino Acids
mannopeptimycin
mannopeptimycin glycopeptide
L-allo-enduracididine
clavaminate synthase
In Vitro Techniques

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Investigating β-hydroxyenduracididine formation in the biosynthesis of the mannopeptimycins. / Haltli, Brad; Tan, Ying; Magarvey, Nathan A.; Wagenaar, Melissa; Yin, Xihou; Greenstein, Michael; Hucul, John A.; Zabriskie, Mark.

In: Chemistry and Biology, Vol. 12, No. 11, 11.2005, p. 1163-1168.

Research output: Contribution to journalArticle

Haltli, B, Tan, Y, Magarvey, NA, Wagenaar, M, Yin, X, Greenstein, M, Hucul, JA & Zabriskie, M 2005, 'Investigating β-hydroxyenduracididine formation in the biosynthesis of the mannopeptimycins', Chemistry and Biology, vol. 12, no. 11, pp. 1163-1168. https://doi.org/10.1016/j.chembiol.2005.09.013
Haltli, Brad ; Tan, Ying ; Magarvey, Nathan A. ; Wagenaar, Melissa ; Yin, Xihou ; Greenstein, Michael ; Hucul, John A. ; Zabriskie, Mark. / Investigating β-hydroxyenduracididine formation in the biosynthesis of the mannopeptimycins. In: Chemistry and Biology. 2005 ; Vol. 12, No. 11. pp. 1163-1168.
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