Hybrid genome-mining/N-NMR was used to target compounds containing piperazate (Piz) residues, leading to the discovery of caveamides A () and B () from 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 -methyl-cyclohexenylalanine residue. Caveamide B () exhibited nanomolar cytotoxicity against several cancer cell lines and nanomolar antimicrobial activity against MRSA and .
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http://dx.doi.org/10.1021/acs.orglett.4c01218 | DOI Listing |
Org Lett
May 2024
Department of Chemistry, The University of British Columbia, Vancouver, British Columbia Canada V6T 1Z4.
Hybrid genome-mining/N-NMR was used to target compounds containing piperazate (Piz) residues, leading to the discovery of caveamides A () and B () from 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 -methyl-cyclohexenylalanine residue.
View Article and Find Full Text PDFMol Plant Pathol
April 2019
Department of Plant Pathology, Ohio State University, Columbus, OH, 43210.
Magnaporthe oryzae is an important fungal pathogen of both rice and wheat. However, how M. oryzae effectors modulate plant immunity is not fully understood.
View Article and Find Full Text PDFChemistry
February 2015
Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).
The total synthesis and stereochemical structural elucidation of JBIR-39, containing four nonproteinogenic piperazic acid (Piz) residues, is reported. The synthesis includes Sc(OTf)3 -catalyzed acylation of a Piz(γ-OTBS) derivative with piperazic acid chloride, providing the desired Piz-Piz(γ-OTBS) dipeptide in high yield without epimerization. After assembling two additional Piz moieties and (S)-isoleucic acid at the N-terminus, amidation with the (R)-α-methylserine ester at the C-terminus, and deprotection afforded the desired (2R,8S)-hexapeptide, which is the assumed structure of JBIR-39.
View Article and Find Full Text PDFGenetics
August 2007
Laboratory of Plant Resistasnce and Genetics, College of Resources and Environmental Sciences, South China Agricultural University, Guangzhou 510642, China.
The indica rice variety Kasalath carries Pi36, a gene that determines resistance to Chinese isolates of rice blast and that has been located to a 17-kb interval on chromosome 8. The genomic sequence of the reference japonica variety Nipponbare was used for an in silico prediction of the resistance (R) gene content of the interval and hence for the identification of candidate gene(s) for Pi36. Three such sequences, which all had both a nucleotide-binding site and a leucine-rich repeat motif, were present.
View Article and Find Full Text PDFJ Immunol
September 1995
Department of Medicine, Jewish Hospital of St. Louis, MO 63110, USA.
The recognition of peptide Ags by T cells through the TCR has exquisite specificity. Cross-reactive T cell responses have been described; however, the structural basis for these responses is not known. We show that two peptides derived from the same protein can exhibit sufficient structural homology, despite minimal structural identity, to elicit cross-reactive T cell responses.
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