Triazole-based reader molecules and methods for synthesizing and use thereof
Triazole-based molecules, methods of making and using the same are provided. Triazole-based molecules may be used as reading molecules and incorporated into or operatively-linked with electrodes, for example, and used in recognition tunneling systems to identify individual and/or sequences of molecules (e.g., DNA bases, carbohydrates, proteins, peptides, and/or amino-acids).
1. A universal reader molecule for functionalization onto electrodes of a recognition tunneling molecule identification system comprising a triazole carboxamide compound of 5-(2-mercaptoethyl)-4H-1,2,4-triazole-3-carboxamide and its tautomers.
2. A compound of formula (1)
3. A method for preparing a triazole compound of claim 2 , comprising:
contacting benzyl mercaptan with 3-bromopropanenitrile in the presence of a base and a first solvent to obtain 3-(benzylthio)propanenitrile;
contacting 3-(benzylthio)propanenitrile with hydrochloric gas in the presence of a second solvent to obtain benzyl 3-(benzylthio)propanimidothioate;
contacting 3-(benzylthio)propanimidothioate with Oxamic acid hydrazide in the presence of a third solvent to obtain 5-(2-(benzylthio)ethyl)-4H-1,2,4-triazole-3-carboxamide; and
contacting 5-(2-(benzylthio)ethyl)-4H-1,2,4-triazole-3-carboxamide with sodium metal and ammonia to obtain 5-(2-mercaptoethyl)-4H-1,2,4-triazole-3-carboxamide.
4. The method of claim 3 , wherein the first solvent is dimethylformamide, the second solvent is diethyl ether, the base is sodium hydride, and the third solvent is pyridine.
5. The method of claim 3 , wherein the base is sodium hydride.
6. The method of claim 3 , wherein the second solvent is diethyl ether.
7. The method of claim 3 , wherein the third solvent is pyridine.
8. A recognition tunneling system comprising at least a pair of electrodes with at least one of which having one or more triazole-based molecules functionalized thereto, wherein the one or more triazole-based molecules comprises 5-(2-mercaptoethyl)-4H-1,2,4-triazole-3-carboxamide.
9. The system of claim 8 , wherein the triazole molecule comprises 5-(2-mercaptoethyl)-4H-1,2,4-triazole-3-carboxamide and its tautomers.
10. The system of claim 8 , wherein the system is configured to identify a sequence of one or more individual DNA bases.
11. The system of claim 8 , wherein the system is configured to identify a sequence of one or more individual sugars, chains of sugars, or oligo- and poly-saccharides.
12. The system of claim 8 , wherein the system is configured to identify a sequence of one or more individual amino acids or proteins/peptides.