An orbitide from Ratibida columnifera seed containing 16 amino acid residues

Mark F. Fisher, Colton D. Payne, K. Johan Rosengren, Joshua S Mylne

Research output: Contribution to journalArticle

Abstract

Cyclic peptides are abundant in plants and have attracted interest due to their bioactivity and potential as drug scaffolds. Orbitides are head-to-tail cyclic peptides that are ribosomally synthesized, post-translationally modified, and lack disulfide bonds. All known orbitides contain 5-12 amino acid residues. Here we describe PLP-53, a novel orbitide from the seed of Ratibida columnifera. PLP-53 consists of 16 amino acids, four residues larger than any known orbitide. NMR structural studies showed that, compared to previously characterized orbitides, PLP-53 is more flexible and, under the studied conditions, did not adopt a single ordered conformation based on analysis of NOEs and chemical shifts.

Original languageEnglish
JournalJournal of Natural Products
DOIs
Publication statusE-pub ahead of print - 8 Aug 2019

Fingerprint

Ratibida
Cyclic Peptides
Seed
Seeds
Amino Acids
Chemical shift
Scaffolds (biology)
Bioactivity
Disulfides
Conformations
Nuclear magnetic resonance
Pharmaceutical Preparations

Cite this

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title = "An orbitide from Ratibida columnifera seed containing 16 amino acid residues",
abstract = "Cyclic peptides are abundant in plants and have attracted interest due to their bioactivity and potential as drug scaffolds. Orbitides are head-to-tail cyclic peptides that are ribosomally synthesized, post-translationally modified, and lack disulfide bonds. All known orbitides contain 5-12 amino acid residues. Here we describe PLP-53, a novel orbitide from the seed of Ratibida columnifera. PLP-53 consists of 16 amino acids, four residues larger than any known orbitide. NMR structural studies showed that, compared to previously characterized orbitides, PLP-53 is more flexible and, under the studied conditions, did not adopt a single ordered conformation based on analysis of NOEs and chemical shifts.",
author = "Fisher, {Mark F.} and Payne, {Colton D.} and Rosengren, {K. Johan} and Mylne, {Joshua S}",
year = "2019",
month = "8",
day = "8",
doi = "10.1021/acs.jnatprod.9b00111",
language = "English",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "Rubber Division of the American Chemical Society",

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An orbitide from Ratibida columnifera seed containing 16 amino acid residues. / Fisher, Mark F.; Payne, Colton D.; Rosengren, K. Johan; Mylne, Joshua S.

In: Journal of Natural Products, 08.08.2019.

Research output: Contribution to journalArticle

TY - JOUR

T1 - An orbitide from Ratibida columnifera seed containing 16 amino acid residues

AU - Fisher, Mark F.

AU - Payne, Colton D.

AU - Rosengren, K. Johan

AU - Mylne, Joshua S

PY - 2019/8/8

Y1 - 2019/8/8

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AB - Cyclic peptides are abundant in plants and have attracted interest due to their bioactivity and potential as drug scaffolds. Orbitides are head-to-tail cyclic peptides that are ribosomally synthesized, post-translationally modified, and lack disulfide bonds. All known orbitides contain 5-12 amino acid residues. Here we describe PLP-53, a novel orbitide from the seed of Ratibida columnifera. PLP-53 consists of 16 amino acids, four residues larger than any known orbitide. NMR structural studies showed that, compared to previously characterized orbitides, PLP-53 is more flexible and, under the studied conditions, did not adopt a single ordered conformation based on analysis of NOEs and chemical shifts.

U2 - 10.1021/acs.jnatprod.9b00111

DO - 10.1021/acs.jnatprod.9b00111

M3 - Article

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

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