Cyaspamide Lab Report
solution to create linear supramolecular assemblies containing thousands of ordered pairs, even without the need for purification.5
With available noncanonical nucleobases to pick from, and evidence of depsipeptides that could be formed in prebiotically plausible ways, David Fialho and Nicholas Hud designed CyAspAmide (ψD). This prebiotically plausible proto-nucleic acid monomer (Figure 1), is the amide formed between a cyanuric acid-functionalized hydroxy acid called 2-OH-CyCo4 (abbreviated as ψ) and the amino acid L-aspartic acid (abbreviated as D). Despite no obvious prebiotic route to this compound, it features certain principles that still apply to prebiotically plausible compounds. More specifically, when simple compounds containing hydroxyl and carboxylic acid moieties are dissolved in water and dried at elevated temperature under acidic conditions, esters can be formed. ψD was designed so that intramolecular esterification (i.e., a lactonization) is possible. This …show more content…
This separated the DBU containing ψ from a beige precipitate that turned out to be mostly CA with some side products. The resulting supernatant was purified using reverse phase chromatography to isolate ψ as its DBU salt. Once dried, the crude product was ran through a cation exchange column using 0.1% formic acid to remove DBU to obtain ψ as its free acid form.
Next, the purified compound was subjected to a Fischer esterification reaction with isopropanol to form the isopropyl ester under acidic conditions (Figure 5). In order to obtain anhydrous HCl, a stock solution was prepared by reacting chlorotrimethylsilane with isopropanol to yield HCl with the protected alcohol as a benign side product. The esterification reaction was allowed to proceed for 6 hours at 100°C. The solvent was removed mostly by blowing nitrogen onto the solution, and the rest was removed by lyophilizing the remaining mixture
With available noncanonical nucleobases to pick from, and evidence of depsipeptides that could be formed in prebiotically plausible ways, David Fialho and Nicholas Hud designed CyAspAmide (ψD). This prebiotically plausible proto-nucleic acid monomer (Figure 1), is the amide formed between a cyanuric acid-functionalized hydroxy acid called 2-OH-CyCo4 (abbreviated as ψ) and the amino acid L-aspartic acid (abbreviated as D). Despite no obvious prebiotic route to this compound, it features certain principles that still apply to prebiotically plausible compounds. More specifically, when simple compounds containing hydroxyl and carboxylic acid moieties are dissolved in water and dried at elevated temperature under acidic conditions, esters can be formed. ψD was designed so that intramolecular esterification (i.e., a lactonization) is possible. This …show more content…
This separated the DBU containing ψ from a beige precipitate that turned out to be mostly CA with some side products. The resulting supernatant was purified using reverse phase chromatography to isolate ψ as its DBU salt. Once dried, the crude product was ran through a cation exchange column using 0.1% formic acid to remove DBU to obtain ψ as its free acid form.
Next, the purified compound was subjected to a Fischer esterification reaction with isopropanol to form the isopropyl ester under acidic conditions (Figure 5). In order to obtain anhydrous HCl, a stock solution was prepared by reacting chlorotrimethylsilane with isopropanol to yield HCl with the protected alcohol as a benign side product. The esterification reaction was allowed to proceed for 6 hours at 100°C. The solvent was removed mostly by blowing nitrogen onto the solution, and the rest was removed by lyophilizing the remaining mixture