Piperazate-Guided Isolation of Caveamides A and B, Cyclohexenylalanine-Containing Nonribosomal Peptides from a Cave Actinomycete

Mostafa Hagar; Kalindi D. Morgan; Spencer D. Stumpf; Maya Tsingos; Carmen A. Banuelos; Marianne D. Sadar; Joshua A.V. Blodgett; Raymond J. Andersen; Katherine S. Ryan

doi:10.1021/acs.orglett.4c01218

Piperazate-Guided Isolation of Caveamides A and B, Cyclohexenylalanine-Containing Nonribosomal Peptides from a Cave Actinomycete

Mostafa Hagar, Kalindi D. Morgan, Spencer D. Stumpf, Maya Tsingos, Carmen A. Banuelos, Marianne D. Sadar, Joshua A.V. Blodgett, Raymond J. Andersen, Katherine S. Ryan

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1 Scopus citations

Abstract

Hybrid genome-mining/¹⁵N-NMR was used to target compounds containing piperazate (Piz) residues, leading to the discovery of caveamides A (1) and B (2) from Streptomyces sp. strain BE230, isolated from New Rankin Cave (Missouri). Caveamides are highly dynamic molecules containing an unprecedented β-ketoamide polyketide fragment, two Piz residues, and a new N-methyl-cyclohexenylalanine residue. Caveamide B (2) exhibited nanomolar cytotoxicity against several cancer cell lines and nanomolar antimicrobial activity against MRSA and E. coli.

Original language	English
Pages (from-to)	4127-4131
Number of pages	5
Journal	Organic Letters
Volume	26
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.4c01218
State	Published - May 17 2024

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title = "Piperazate-Guided Isolation of Caveamides A and B, Cyclohexenylalanine-Containing Nonribosomal Peptides from a Cave Actinomycete",

abstract = "Hybrid genome-mining/15N-NMR was used to target compounds containing piperazate (Piz) residues, leading to the discovery of caveamides A (1) and B (2) from Streptomyces sp. strain BE230, isolated from New Rankin Cave (Missouri). Caveamides are highly dynamic molecules containing an unprecedented β-ketoamide polyketide fragment, two Piz residues, and a new N-methyl-cyclohexenylalanine residue. Caveamide B (2) exhibited nanomolar cytotoxicity against several cancer cell lines and nanomolar antimicrobial activity against MRSA and E. coli.",

author = "Mostafa Hagar and Morgan, {Kalindi D.} and Stumpf, {Spencer D.} and Maya Tsingos and Banuelos, {Carmen A.} and Sadar, {Marianne D.} and Blodgett, {Joshua A.V.} and Andersen, {Raymond J.} and Ryan, {Katherine S.}",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = may,

day = "17",

doi = "10.1021/acs.orglett.4c01218",

language = "English",

volume = "26",

pages = "4127--4131",

journal = "Organic Letters",

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TY - JOUR

T1 - Piperazate-Guided Isolation of Caveamides A and B, Cyclohexenylalanine-Containing Nonribosomal Peptides from a Cave Actinomycete

AU - Hagar, Mostafa

AU - Morgan, Kalindi D.

AU - Stumpf, Spencer D.

AU - Tsingos, Maya

AU - Banuelos, Carmen A.

AU - Sadar, Marianne D.

AU - Blodgett, Joshua A.V.

AU - Andersen, Raymond J.

AU - Ryan, Katherine S.

PY - 2024/5/17

Y1 - 2024/5/17

N2 - Hybrid genome-mining/15N-NMR was used to target compounds containing piperazate (Piz) residues, leading to the discovery of caveamides A (1) and B (2) from Streptomyces sp. strain BE230, isolated from New Rankin Cave (Missouri). Caveamides are highly dynamic molecules containing an unprecedented β-ketoamide polyketide fragment, two Piz residues, and a new N-methyl-cyclohexenylalanine residue. Caveamide B (2) exhibited nanomolar cytotoxicity against several cancer cell lines and nanomolar antimicrobial activity against MRSA and E. coli.

AB - Hybrid genome-mining/15N-NMR was used to target compounds containing piperazate (Piz) residues, leading to the discovery of caveamides A (1) and B (2) from Streptomyces sp. strain BE230, isolated from New Rankin Cave (Missouri). Caveamides are highly dynamic molecules containing an unprecedented β-ketoamide polyketide fragment, two Piz residues, and a new N-methyl-cyclohexenylalanine residue. Caveamide B (2) exhibited nanomolar cytotoxicity against several cancer cell lines and nanomolar antimicrobial activity against MRSA and E. coli.

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U2 - 10.1021/acs.orglett.4c01218

DO - 10.1021/acs.orglett.4c01218

M3 - Article

C2 - 38718303

AN - SCOPUS:85193224154

SN - 1523-7060

VL - 26

SP - 4127

EP - 4131

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Piperazate-Guided Isolation of Caveamides A and B, Cyclohexenylalanine-Containing Nonribosomal Peptides from a Cave Actinomycete

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