Total synthesis, structure elucidation, and bioactivity evaluation of the cyclic lipopeptide natural product Paenilipoheptin A

Vladyslav Lysenko; Nataliia V. Machushynets; Jisca L. van Dam; Fabienne A.C. Sterk; Alexander Speer; Arthur F.J. Ram; Cornelis J. Slingerland; Gilles P. Van Wezel; Nathaniel I. Martin

doi:10.1021/acs.orglett.5c00232

Total synthesis, structure elucidation, and bioactivity evaluation of the cyclic lipopeptide natural product Paenilipoheptin A

Vladyslav Lysenko
, Nataliia V. Machushynets
, Jisca L. van Dam
, Fabienne A.C. Sterk
, Alexander Speer
, Arthur F.J. Ram
, Cornelis J. Slingerland
, Gilles P. Van Wezel^* (Co-auteur)
, Nathaniel I. Martin^* (Co-auteur)

^*Corresponding author voor dit werk

NIOO - Microbial Ecology (ME)

Onderzoeksoutput: Bijdrage aan wetenschappelijk tijdschrift/periodieke uitgave › Artikel › Wetenschappelijk › peer review

1 Citaat (Scopus)

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In this study, we further investigated the structure of the recently reported cyclic lipopeptide natural product paenilipoheptin A. Here, we disclose the first total synthesis of the compound, allowing for its complete structural assignment. The route developed employs automated SPPS, providing access to the compound in quantities suitable for antibacterial and antifungal testing. These studies unequivocally establish the stereochemical framework of paenilipoheptin A and further reveal that the compound possesses moderate activity against Gram-positive bacteria.

Originele taal-2	Engels
Pagina's (van-tot)	2826–2831
Tijdschrift	Organic Letters
Volume	27
Nummer van het tijdschrift	12
DOI's	https://doi.org/10.1021/acs.orglett.5c00232
Status	Gepubliceerd - 28 mrt. 2025

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10.1021/acs.orglett.5c00232Licentie: CC BY

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title = "Total synthesis, structure elucidation, and bioactivity evaluation of the cyclic lipopeptide natural product Paenilipoheptin A",

abstract = "In this study, we further investigated the structure of the recently reported cyclic lipopeptide natural product paenilipoheptin A. Here, we disclose the first total synthesis of the compound, allowing for its complete structural assignment. The route developed employs automated SPPS, providing access to the compound in quantities suitable for antibacterial and antifungal testing. These studies unequivocally establish the stereochemical framework of paenilipoheptin A and further reveal that the compound possesses moderate activity against Gram-positive bacteria.",

author = "Vladyslav Lysenko and Machushynets, \{Nataliia V.\} and \{van Dam\}, \{Jisca L.\} and Sterk, \{Fabienne A.C.\} and Alexander Speer and Ram, \{Arthur F.J.\} and Slingerland, \{Cornelis J.\} and \{Van Wezel\}, \{Gilles P.\} and Martin, \{Nathaniel I.\}",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society.",

year = "2025",

month = mar,

day = "28",

doi = "10.1021/acs.orglett.5c00232",

language = "English",

volume = "27",

pages = "2826–2831",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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}

Total synthesis, structure elucidation, and bioactivity evaluation of the cyclic lipopeptide natural product Paenilipoheptin A. / Lysenko, Vladyslav; Machushynets, Nataliia V.; van Dam, Jisca L. et al.
In: Organic Letters, Vol. 27, Nr. 12, 28.03.2025, blz. 2826–2831.

Onderzoeksoutput: Bijdrage aan wetenschappelijk tijdschrift/periodieke uitgave › Artikel › Wetenschappelijk › peer review

TY - JOUR

T1 - Total synthesis, structure elucidation, and bioactivity evaluation of the cyclic lipopeptide natural product Paenilipoheptin A

AU - Lysenko, Vladyslav

AU - Machushynets, Nataliia V.

AU - van Dam, Jisca L.

AU - Sterk, Fabienne A.C.

AU - Speer, Alexander

AU - Ram, Arthur F.J.

AU - Slingerland, Cornelis J.

AU - Van Wezel, Gilles P.

AU - Martin, Nathaniel I.

PY - 2025/3/28

Y1 - 2025/3/28

N2 - In this study, we further investigated the structure of the recently reported cyclic lipopeptide natural product paenilipoheptin A. Here, we disclose the first total synthesis of the compound, allowing for its complete structural assignment. The route developed employs automated SPPS, providing access to the compound in quantities suitable for antibacterial and antifungal testing. These studies unequivocally establish the stereochemical framework of paenilipoheptin A and further reveal that the compound possesses moderate activity against Gram-positive bacteria.

AB - In this study, we further investigated the structure of the recently reported cyclic lipopeptide natural product paenilipoheptin A. Here, we disclose the first total synthesis of the compound, allowing for its complete structural assignment. The route developed employs automated SPPS, providing access to the compound in quantities suitable for antibacterial and antifungal testing. These studies unequivocally establish the stereochemical framework of paenilipoheptin A and further reveal that the compound possesses moderate activity against Gram-positive bacteria.

U2 - 10.1021/acs.orglett.5c00232

DO - 10.1021/acs.orglett.5c00232

M3 - Article

AN - SCOPUS:105000393352

SN - 1523-7060

VL - 27

SP - 2826

EP - 2831

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Total synthesis, structure elucidation, and bioactivity evaluation of the cyclic lipopeptide natural product Paenilipoheptin A

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