Crossiellidines A-F, Unprecedented Pyrazine-Alkylguanidine Metabolites with Broad-Spectrum Antibacterial Activity from Crossiella sp.

Francisco Javier Ortiz-López; Daniel Oves-Costales; Daniel Carretero-Molina; Jesús Martín; Caridad Díaz; Mercedes de la Cruz; Fernando Román-Hurtado; María Álvarez-Arévalo; Tue Sparholt Jørgensen; Fernando Reyes; Tilmann Weber; Olga Genilloud

doi:10.1021/acs.orglett.3c01088

Crossiellidines A-F, Unprecedented Pyrazine-Alkylguanidine Metabolites with Broad-Spectrum Antibacterial Activity from Crossiella sp.

Francisco Javier Ortiz-López^*, Daniel Oves-Costales, Daniel Carretero-Molina, Jesús Martín, Caridad Díaz, Mercedes de la Cruz, Fernando Román-Hurtado, María Álvarez-Arévalo, Tue Sparholt Jørgensen, Fernando Reyes, Tilmann Weber, Olga Genilloud^*

^*Corresponding author for this work

Fundación MEDINA

Research output: Contribution to journal › Letter › peer-review

Abstract

Crosiellidines are intriguing pyrazine-alkylguanidine metabolites isolated from the minor actinomycete genus Crossiella. Their structures present an unprecedented 2-methoxy-3,5,6-trialkyl pyrazine scaffold and uncommon guanidine prenylations, including an exotic O-prenylated N-hydroxyguanidine moiety. The novel substitution pattern of the 2-methoxypyrazine core inaugurates a new class of naturally occurring pyrazine compounds, the biosynthetic implications of which are discussed herein. Isotopic feeding and genome analysis allowed us to propose a biosynthetic pathway from arginine. The crossiellidines exhibited remarkable, broad-spectrum antibacterial activity.

Original language	English
Journal	Organic Letters
Volume	25
Pages (from-to)	3502-3507
Number of pages	4
ISSN	1523-7060
DOIs	https://doi.org/10.1021/acs.orglett.3c01088
Publication status	Published - 2023

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Ortiz-López, F. J., Oves-Costales, D., Carretero-Molina, D., Martín, J., Díaz, C., de la Cruz, M., Román-Hurtado, F., Álvarez-Arévalo, M., Jørgensen, T. S., Reyes, F., Weber, T., & Genilloud, O. (2023). Crossiellidines A-F, Unprecedented Pyrazine-Alkylguanidine Metabolites with Broad-Spectrum Antibacterial Activity from Crossiella sp. Organic Letters, 25, 3502-3507. https://doi.org/10.1021/acs.orglett.3c01088

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title = "Crossiellidines A-F, Unprecedented Pyrazine-Alkylguanidine Metabolites with Broad-Spectrum Antibacterial Activity from Crossiella sp.",

abstract = "Crosiellidines are intriguing pyrazine-alkylguanidine metabolites isolated from the minor actinomycete genus Crossiella. Their structures present an unprecedented 2-methoxy-3,5,6-trialkyl pyrazine scaffold and uncommon guanidine prenylations, including an exotic O-prenylated N-hydroxyguanidine moiety. The novel substitution pattern of the 2-methoxypyrazine core inaugurates a new class of naturally occurring pyrazine compounds, the biosynthetic implications of which are discussed herein. Isotopic feeding and genome analysis allowed us to propose a biosynthetic pathway from arginine. The crossiellidines exhibited remarkable, broad-spectrum antibacterial activity.",

author = "Ortiz-L{\'o}pez, {Francisco Javier} and Daniel Oves-Costales and Daniel Carretero-Molina and Jes{\'u}s Mart{\'i}n and Caridad D{\'i}az and {de la Cruz}, Mercedes and Fernando Rom{\'a}n-Hurtado and Mar{\'i}a {\'A}lvarez-Ar{\'e}valo and J{\o}rgensen, {Tue Sparholt} and Fernando Reyes and Tilmann Weber and Olga Genilloud",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

doi = "10.1021/acs.orglett.3c01088",

language = "English",

volume = "25",

pages = "3502--3507",

journal = "Organic Letters",

issn = "1523-7060",

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Ortiz-López, FJ, Oves-Costales, D, Carretero-Molina, D, Martín, J, Díaz, C, de la Cruz, M, Román-Hurtado, F, Álvarez-Arévalo, M, Jørgensen, TS, Reyes, F, Weber, T & Genilloud, O 2023, 'Crossiellidines A-F, Unprecedented Pyrazine-Alkylguanidine Metabolites with Broad-Spectrum Antibacterial Activity from Crossiella sp.', Organic Letters, vol. 25, pp. 3502-3507. https://doi.org/10.1021/acs.orglett.3c01088

TY - JOUR

T1 - Crossiellidines A-F, Unprecedented Pyrazine-Alkylguanidine Metabolites with Broad-Spectrum Antibacterial Activity from Crossiella sp.

AU - Ortiz-López, Francisco Javier

AU - Oves-Costales, Daniel

AU - Carretero-Molina, Daniel

AU - Martín, Jesús

AU - Díaz, Caridad

AU - de la Cruz, Mercedes

AU - Román-Hurtado, Fernando

AU - Álvarez-Arévalo, María

AU - Jørgensen, Tue Sparholt

AU - Reyes, Fernando

AU - Weber, Tilmann

AU - Genilloud, Olga

PY - 2023

Y1 - 2023

N2 - Crosiellidines are intriguing pyrazine-alkylguanidine metabolites isolated from the minor actinomycete genus Crossiella. Their structures present an unprecedented 2-methoxy-3,5,6-trialkyl pyrazine scaffold and uncommon guanidine prenylations, including an exotic O-prenylated N-hydroxyguanidine moiety. The novel substitution pattern of the 2-methoxypyrazine core inaugurates a new class of naturally occurring pyrazine compounds, the biosynthetic implications of which are discussed herein. Isotopic feeding and genome analysis allowed us to propose a biosynthetic pathway from arginine. The crossiellidines exhibited remarkable, broad-spectrum antibacterial activity.

AB - Crosiellidines are intriguing pyrazine-alkylguanidine metabolites isolated from the minor actinomycete genus Crossiella. Their structures present an unprecedented 2-methoxy-3,5,6-trialkyl pyrazine scaffold and uncommon guanidine prenylations, including an exotic O-prenylated N-hydroxyguanidine moiety. The novel substitution pattern of the 2-methoxypyrazine core inaugurates a new class of naturally occurring pyrazine compounds, the biosynthetic implications of which are discussed herein. Isotopic feeding and genome analysis allowed us to propose a biosynthetic pathway from arginine. The crossiellidines exhibited remarkable, broad-spectrum antibacterial activity.

U2 - 10.1021/acs.orglett.3c01088

DO - 10.1021/acs.orglett.3c01088

M3 - Letter

C2 - 37162500

AN - SCOPUS:85159770177

SN - 1523-7060

VL - 25

SP - 3502

EP - 3507

JO - Organic Letters

JF - Organic Letters

ER -

Crossiellidines A-F, Unprecedented Pyrazine-Alkylguanidine Metabolites with Broad-Spectrum Antibacterial Activity from Crossiella sp.

Abstract

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