Structural revision of burkholdine-1215, a cyclic octapeptide isolated from <i>Burkholderia</i>

We revised a structure of burkholdine (Bk)-1215, a cyclic octalipopeptide isolated from <i>Burkholderia</i>. We synthesised both α- and β-isomers of 1-methylethyl-D-xylopyranoside and compared them to the isolated moiety by NMR analysis. SPARTAN simulation was then performed to establish the stereochemistry of the anomeric position as the β-isomer. Additionally, the NMR assignment of the ATHOD moiety was revised using 2D-NMR analysis. Finally, the γ-linkage between the D-Dab and β-OHTyr residues was determined.

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Publication Details

Journal
Natural Product Research
Published
2025-12-11
DOI
https://doi.org/10.1080/14786419.2025.2602041
Primary Topic
Microbial Natural Products and Biosynthesis
Type
article
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article

Structural revision of burkholdine-1215, a cyclic octapeptide isolated from Burkholderia

Shigekazu Yano, Rin Kainuma, Hiroyuki Konno, Shou Sasaki
Natural Product Research
Microbial Natural Products and Biosynthesis
article

Structural revision of burkholdine-1215, a cyclic octapeptide isolated from Burkholderia

Shigekazu Yano, Rin Kainuma, Hiroyuki Konno, Shou Sasaki
article en

Abstract

We revised a structure of burkholdine (Bk)-1215, a cyclic octalipopeptide isolated from <i>Burkholderia</i>. We synthesised both α- and β-isomers of 1-methylethyl-D-xylopyranoside and compared them to the isolated moiety by NMR analysis. SPARTAN simulation was then performed to establish the stereochemistry of the anomeric position as the β-isomer. Additionally, the NMR assignment of the ATHOD moiety was revised using 2D-NMR analysis. Finally, the γ-linkage between the D-Dab and β-OHTyr residues was determined.

Natural Product Research
Yamagata University (JP)
Openalex Percentile: Top 57%
Microbial Natural Products and Biosynthesis
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