Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril

Lidia Strimbu Berbeci, Wei Wang, Angel Kaifer

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

(Figure Presented) The cucurbit[6]uril (CB6) host forms stable complexes with 2-aminoethanethiol (cysteamine) and a derivative that contains a bulky terminal group attached to the amine group, as well as with the related disulfide cystamine. In these complexes, the thiol or the disulfide group is encapsulated inside the host cavity. The CB6-complexed thiols show drastically decreased reactivity with several oxidants, while the CB6-bound disulfide also exhibits hindered reactivity with reducing agents, such as dithiothreitol.

Original languageEnglish
Pages (from-to)3721-3724
Number of pages4
JournalOrganic Letters
Volume10
Issue number17
DOIs
StatePublished - Dec 1 2008

Fingerprint

disulfides
Sulfhydryl Compounds
thiols
Disulfides
Cysteamine
reactivity
Cystamine
cysteamine
Dithiothreitol
Reducing Agents
Oxidants
Amines
amines
Derivatives
cavities
cucurbit(6)uril

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril. / Berbeci, Lidia Strimbu; Wang, Wei; Kaifer, Angel.

In: Organic Letters, Vol. 10, No. 17, 01.12.2008, p. 3721-3724.

Research output: Contribution to journalArticle

Berbeci, Lidia Strimbu ; Wang, Wei ; Kaifer, Angel. / Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril. In: Organic Letters. 2008 ; Vol. 10, No. 17. pp. 3721-3724.
@article{140d3c72c58f48f9928e54e4c147ebdc,
title = "Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril",
abstract = "(Figure Presented) The cucurbit[6]uril (CB6) host forms stable complexes with 2-aminoethanethiol (cysteamine) and a derivative that contains a bulky terminal group attached to the amine group, as well as with the related disulfide cystamine. In these complexes, the thiol or the disulfide group is encapsulated inside the host cavity. The CB6-complexed thiols show drastically decreased reactivity with several oxidants, while the CB6-bound disulfide also exhibits hindered reactivity with reducing agents, such as dithiothreitol.",
author = "Berbeci, {Lidia Strimbu} and Wei Wang and Angel Kaifer",
year = "2008",
month = "12",
day = "1",
doi = "10.1021/ol8013667",
language = "English",
volume = "10",
pages = "3721--3724",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Drastically decreased reactivity of thiols and disulfides complexed by cucurbit[6]uril

AU - Berbeci, Lidia Strimbu

AU - Wang, Wei

AU - Kaifer, Angel

PY - 2008/12/1

Y1 - 2008/12/1

N2 - (Figure Presented) The cucurbit[6]uril (CB6) host forms stable complexes with 2-aminoethanethiol (cysteamine) and a derivative that contains a bulky terminal group attached to the amine group, as well as with the related disulfide cystamine. In these complexes, the thiol or the disulfide group is encapsulated inside the host cavity. The CB6-complexed thiols show drastically decreased reactivity with several oxidants, while the CB6-bound disulfide also exhibits hindered reactivity with reducing agents, such as dithiothreitol.

AB - (Figure Presented) The cucurbit[6]uril (CB6) host forms stable complexes with 2-aminoethanethiol (cysteamine) and a derivative that contains a bulky terminal group attached to the amine group, as well as with the related disulfide cystamine. In these complexes, the thiol or the disulfide group is encapsulated inside the host cavity. The CB6-complexed thiols show drastically decreased reactivity with several oxidants, while the CB6-bound disulfide also exhibits hindered reactivity with reducing agents, such as dithiothreitol.

UR - http://www.scopus.com/inward/record.url?scp=55949097948&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=55949097948&partnerID=8YFLogxK

U2 - 10.1021/ol8013667

DO - 10.1021/ol8013667

M3 - Article

C2 - 18683939

AN - SCOPUS:55949097948

VL - 10

SP - 3721

EP - 3724

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 17

ER -