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Ring Opening of 6‐Azabicyclo[3.1.0]hex‐3‐en‐2‐ols in Water under Mild Conditions
Author(s) -
Vale João R.,
Siopa Filipa,
Branco Paula S.,
Afonso Carlos A. M.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501468
Subject(s) - chemistry , aziridine , nucleophile , bioconjugation , reactivity (psychology) , ring (chemistry) , alkyl , sulfur , pyridine , medicinal chemistry , cysteine , aryl , organic chemistry , nitrogen , combinatorial chemistry , catalysis , enzyme , medicine , alternative medicine , pathology
The ring‐opening reaction of α‐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 °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 α‐hydroxycyclopenteno‐aziridine with the peptide hormone salmon calcitonin (sCT).