Ring Opening of 6-Azabicyclo[3.1.0]hex-3-en-2-ols in Water under Mild Conditions

Joao R. Vale; Filipa Siopa; Paula Cristina de Sério Branco; Carlos A M Afonso

doi:10.1002/ejoc.201501468

Ring Opening of 6-Azabicyclo[3.1.0]hex-3-en-2-ols in Water under Mild Conditions

Joao R. Vale, Filipa Siopa, Paula Cristina de Sério Branco, Carlos A M Afonso

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

The ring-opening reaction of -hydroxycyclopenteno-aziridines (6-azabicyclo[3.1.0]hex-3-en-2-ols) was investigated in water and under physiological conditions (pH = 7.4) at 37 degrees C by using a range of carbon-, oxygen-, nitrogen-, and sulfur-containing nucleophiles such as azides, anilines, and thiols (aryl and alkyl thiols as well as cysteine and its derivatives), which provided the products in moderate to high isolated yields. The reactivity was also demonstrated in the bioconjugation of -hydroxycyclopenteno-aziridine with the peptide hormone salmon calcitonin (sCT).

Original language	English
Pages (from-to)	2048-2053
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	11
DOIs	https://doi.org/10.1002/ejoc.201501468
Publication status	Published - Apr 2016

Keywords

Water chemistry
Nucleophilic substitution
Chemoselectivity
Fused-ring systems
Carbocycles

Access to Document

10.1002/ejoc.201501468Licence: Unspecified

Cite this

@article{062adef8e63941ae96eb8bf5aecf1797,

title = "Ring Opening of 6-Azabicyclo[3.1.0]hex-3-en-2-ols in Water under Mild Conditions",

abstract = "The ring-opening reaction of -hydroxycyclopenteno-aziridines (6-azabicyclo[3.1.0]hex-3-en-2-ols) was investigated in water and under physiological conditions (pH = 7.4) at 37 degrees C by using a range of carbon-, oxygen-, nitrogen-, and sulfur-containing nucleophiles such as azides, anilines, and thiols (aryl and alkyl thiols as well as cysteine and its derivatives), which provided the products in moderate to high isolated yields. The reactivity was also demonstrated in the bioconjugation of -hydroxycyclopenteno-aziridine with the peptide hormone salmon calcitonin (sCT).",

keywords = "Water chemistry, Nucleophilic substitution, Chemoselectivity, Fused-ring systems, Carbocycles",

author = "Vale, {Joao R.} and Filipa Siopa and Branco, {Paula Cristina de S{\'e}rio} and Afonso, {Carlos A M}",

note = "Sem PDF. Fundacao para a Ciencia e a Tecnologia (FCT) (SFRH/BPD/88666/2012; PTDC/QUI-QUI/119823/2010, UID/DTP/04138/2013) ",

year = "2016",

month = apr,

doi = "10.1002/ejoc.201501468",

language = "English",

volume = "11",

pages = "2048--2053",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley",

}

TY - JOUR

T1 - Ring Opening of 6-Azabicyclo[3.1.0]hex-3-en-2-ols in Water under Mild Conditions

AU - Vale, Joao R.

AU - Siopa, Filipa

AU - Branco, Paula Cristina de Sério

AU - Afonso, Carlos A M

N1 - Sem PDF. Fundacao para a Ciencia e a Tecnologia (FCT) (SFRH/BPD/88666/2012; PTDC/QUI-QUI/119823/2010, UID/DTP/04138/2013)

PY - 2016/4

Y1 - 2016/4

N2 - The ring-opening reaction of -hydroxycyclopenteno-aziridines (6-azabicyclo[3.1.0]hex-3-en-2-ols) was investigated in water and under physiological conditions (pH = 7.4) at 37 degrees C by using a range of carbon-, oxygen-, nitrogen-, and sulfur-containing nucleophiles such as azides, anilines, and thiols (aryl and alkyl thiols as well as cysteine and its derivatives), which provided the products in moderate to high isolated yields. The reactivity was also demonstrated in the bioconjugation of -hydroxycyclopenteno-aziridine with the peptide hormone salmon calcitonin (sCT).

AB - The ring-opening reaction of -hydroxycyclopenteno-aziridines (6-azabicyclo[3.1.0]hex-3-en-2-ols) was investigated in water and under physiological conditions (pH = 7.4) at 37 degrees C by using a range of carbon-, oxygen-, nitrogen-, and sulfur-containing nucleophiles such as azides, anilines, and thiols (aryl and alkyl thiols as well as cysteine and its derivatives), which provided the products in moderate to high isolated yields. The reactivity was also demonstrated in the bioconjugation of -hydroxycyclopenteno-aziridine with the peptide hormone salmon calcitonin (sCT).

KW - Water chemistry

KW - Nucleophilic substitution

KW - Chemoselectivity

KW - Fused-ring systems

KW - Carbocycles

U2 - 10.1002/ejoc.201501468

DO - 10.1002/ejoc.201501468

M3 - Article

SN - 1434-193X

VL - 11

SP - 2048

EP - 2053

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

Ring Opening of 6-Azabicyclo[3.1.0]hex-3-en-2-ols in Water under Mild Conditions

Abstract

Keywords

Access to Document

Fingerprint

Cite this