Methods for labeling a substrate having a plurality of thiol groups attached thereto
AssigneeUniversity of Georgia Research Foundation, Inc. Boyd Graduate Studies Research Center
InventorsVLADIMIR POPIK, SELVANATHAN ARUMUGAM
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Abstract
Methods for derivatizing the surface of a substrate having a plurality of thiol groups thereon are disclosed herein. The method can include reacting the thiol groups with an o-quinone methide, which can optionally be generated by irradiating an o-quinone methide precursor compound. In some embodiments, the method can advantageously be reversible. Exemplary o-quinone methides having a cyclic alkyne attached thereto, and precursor compounds for generating such compounds, are also disclosed herein.
Claims28
A method for derivatizing the surface of a substrate, the method comprising:
- generating an o-quinone methide having the foiinula:
- and
- contacting the o-quinone methide with a substrate having a plurality of thiol groups attached thereto under conditions effective to form a plurality of thioethers, wherein:
- each R1 is independently H, halogen, or an organic group;
- and
- optionally, two or more R1 groups may be combined to form one or more rings.
A method for derivatizing the surface of a substrate, the method comprising:
- providing a first precursor compound having the formula:
- irradiating the first precursor compound under conditions effective to form a first o-quinone methide having the formula:
- and
- contacting the first o-quinone methide with a substrate having a plurality of thiol groups attached thereto under conditions effective to form a plurality of thioethers from the reaction of the first o-quinone methide with the plurality of thiols,
- wherein:
- each R1 is independently H, halogen, or an organic group;
- Y is OR5, NR52, NR53+(Z1/q)− wherein Z is an anion having a negative charge of q;
- each R5 is independently H or an organic group;
- optionally, two or more R1 groups may be combined to form one or more rings;
- and
- optionally, two or more R5 groups may be combined to form one or more rings.
A substrate having a derivatized surface comprising a compound having the formula:
- wherein:
- each R1 is independently H, halogen, or an organic group;
- optionally, two or more R1 groups may be combined to form one or more rings;
- and
- Y is a sulfur atom attached to the surface of the substrate.
A precursor compound having the formula:
- wherein:
- each R1 is independently H, halogen, or an organic group;
- Y is OR5, NR52, NR53+(Z1/q)− wherein Z is an anion having a negative charge of q;
- each R5 is independently H or an organic group;
- optionally, two or more R1 groups may be combined to form one or more rings;
- optionally, two or more R5 groups may be combined to form one or more rings;
- and
- with the proviso that the precursor compound comprises a cyclic alkyne attached thereto.
An o-quinone methide having the formula:
- wherein:
- each R1 is independently H, halogen, or an organic group;
- optionally two or more R1 groups may be combined to form one or more rings;
- and
- with the proviso that the o-quinone methide comprises a cyclic alkyne attached thereto.
Dependencies are inferred from the claim text.