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C‐3β‐Tethered Functional Cholesterol Conjugates by Nitrile Oxide Alkyne Cycloaddition (NOAC)
Author(s) -
Algay Virginie,
O'Sullivan Justine,
Heaney Frances
Publication year - 2014
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.201301822
Subject(s) - nitrile , chemistry , alkyne , cycloaddition , isoxazole , covalent bond , conjugate , combinatorial chemistry , oxide , click chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
Covalent cholesterol conjugates have been prepared by isoxazole‐generating [3+2] nitrile oxide alkyne cycloaddition (NOAC) chemistry. Steroidal building blocks functionalised with either an alkyne or a nitrile oxide precursor were evaluated. The reaction has been demonstrated for the tethering to cholesterol of groups capable of bioreporting, and for the formation of cholesterol–biomolecule conjugates.