Facile method to sequence cyclic peptides/peptoids via one-pot ring-opening/cleavage reaction

Kang Ju Lee, Hyun-Suk Lim

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A facile method for sequence determination of cyclic peptides/peptoids is described. Macrocyclic peptides/peptoids of 3-10 residues were efficiently synthesized through thioether formation. One-pot reaction of thioether-embedded cyclic peptides/peptoids involving cyanogen bromide-mediated ring-opening and cleavage provides linearized molecules, which can be efficiently sequenced by tandem mass spectrometry.

Original languageEnglish
Pages (from-to)5710-5713
Number of pages4
JournalOrganic Letters
Volume16
Issue number21
DOIs
StatePublished - Nov 7 2014

Fingerprint

Peptoids
Cyclic Peptides
peptides
cleavage
Sulfides
rings
cyanogen
Cyanogen Bromide
Tandem Mass Spectrometry
Mass spectrometry
Sequence Analysis
bromides
mass spectroscopy
Peptides
Molecules
molecules

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Medicine(all)

Cite this

Facile method to sequence cyclic peptides/peptoids via one-pot ring-opening/cleavage reaction. / Lee, Kang Ju; Lim, Hyun-Suk.

In: Organic Letters, Vol. 16, No. 21, 07.11.2014, p. 5710-5713.

Research output: Contribution to journalArticle

@article{af7911966d914c42b8b6e5b99b4d74eb,
title = "Facile method to sequence cyclic peptides/peptoids via one-pot ring-opening/cleavage reaction",
abstract = "A facile method for sequence determination of cyclic peptides/peptoids is described. Macrocyclic peptides/peptoids of 3-10 residues were efficiently synthesized through thioether formation. One-pot reaction of thioether-embedded cyclic peptides/peptoids involving cyanogen bromide-mediated ring-opening and cleavage provides linearized molecules, which can be efficiently sequenced by tandem mass spectrometry.",
author = "Lee, {Kang Ju} and Hyun-Suk Lim",
year = "2014",
month = "11",
day = "7",
doi = "10.1021/ol502788e",
language = "English",
volume = "16",
pages = "5710--5713",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "21",

}

TY - JOUR

T1 - Facile method to sequence cyclic peptides/peptoids via one-pot ring-opening/cleavage reaction

AU - Lee, Kang Ju

AU - Lim, Hyun-Suk

PY - 2014/11/7

Y1 - 2014/11/7

N2 - A facile method for sequence determination of cyclic peptides/peptoids is described. Macrocyclic peptides/peptoids of 3-10 residues were efficiently synthesized through thioether formation. One-pot reaction of thioether-embedded cyclic peptides/peptoids involving cyanogen bromide-mediated ring-opening and cleavage provides linearized molecules, which can be efficiently sequenced by tandem mass spectrometry.

AB - A facile method for sequence determination of cyclic peptides/peptoids is described. Macrocyclic peptides/peptoids of 3-10 residues were efficiently synthesized through thioether formation. One-pot reaction of thioether-embedded cyclic peptides/peptoids involving cyanogen bromide-mediated ring-opening and cleavage provides linearized molecules, which can be efficiently sequenced by tandem mass spectrometry.

UR - http://www.scopus.com/inward/record.url?scp=84909989924&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84909989924&partnerID=8YFLogxK

U2 - 10.1021/ol502788e

DO - 10.1021/ol502788e

M3 - Article

C2 - 25310875

AN - SCOPUS:84909989924

VL - 16

SP - 5710

EP - 5713

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 21

ER -