Alkynes and methods of reacting alkynes with 1,3-dipole-functional compounds
1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also disclosed. The reaction of 1,3-dipole-functional compounds with alkynes can be used for a wide variety of applications including the immobilization of biomolecules on a substrate.
1. A dibenzocyclooctyne having the formula:
wherein:
each R 1 and R 2 is hydrogen;
X represents CHOR 3 ; and
R 3 represents an organic group comprising a biotin fragment.
2. A dibenzocyclooctyne having the formula:
wherein:
each R 1 and R 2 is hydrogen;
X represents CHOR 3 ; and
R 3 represents an organic group comprising a covalently bound organic dye.
3. A dibenzocyclooctyne having the formula:
wherein:
each R 1 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
each R 2 is independently selected from the group consisting of hydrogen, halogen, hydroxy, alkoxy, nitrate, nitrite, sulfate, and a C1-C10 organic group;
X represents C═N—OR 3 , C═N—NR 3 R 4 , CHOR 3 , or CHNHR 3 ;
R 3 represents an organic group attached to a nanoparticle; and
R 4 represents hydrogen or an organic group.
4. A method of preparing a heterocyclic compound, the method comprising:
combining at least one azide-functional compound with at least one dibenzocyclooctyne according to claim 3 ; and
allowing the at least one azide-functional compound and the at least one alkyne to react under conditions effective to form the heterocyclic compound.
5. An alkyne of the formula:
wherein:
each R 1 and R 2 is hydrogen;
X represents CHOR 3 ; and
R 3 represents an organic group.