A Novel N-(Pyrrolidinyl-2-methyl)glycine-Based PNA with a Strong Preference for RNA over DNA

Abstract

A novel, N-(pyrrolidinyl-2-methyl)glycine-based (Pmgbased) PNA is introduced. The synthesis of the backbone was accomplished in good yield, starting from prolinol. Thymine (S)-and (R)-Pmg and adenine-and cytosine-derived (R)-Pmg monomers were prepared. Five different fragments − two with either the (R) or the (S) isomer of the thymine Pmg monomer, two oligomers with two consecutive (R)-or (S)-thymine Pmg units, and fully modified (R)-Pmg decamer − were assembled on a solid support. UV thermal melting experiments with complementary DNA and RNA were performed in order to determine the effects of conformational restriction, steric hindrance, and chirality on the

Synthesis of Sulfur-Rich Crown Ethers via Azide–Alkyne Macrocyclization of α,ω-Diazido- and α,ω-Dipropargyl Sulfide Derivatives

“…In conclusion, a series of organic diazides and dithiols were prepared by modified Appel reaction and applied for the construction of a new class of sulfur-rich macrocycles 14 decorated with 1,2,3-triazole as an adjuvant complexing moiety. 8,21 Although some of the key substrates 1-4 are known in the literature, 22 the presented one-pot protocol nicely supplement multistep syntheses described thus far. The final macrocyclic compounds are of our interest in the context of their potential complexing properties towards heavy-metal ions evidenced for other sulfurated crown ethers.…”

Synthesis of Sulfur-Rich Crown Ethers via Azide–Alkyne Macrocyclization of α,ω-Diazido- and α,ω-Dipropargyl Sulfide Derivatives

“…In conclusion, a series of organic diazides and dithiols were prepared by modified Appel reaction and applied for the construction of a new class of sulfur-rich macrocycles 14 decorated with 1,2,3-triazole as an adjuvant complexing moiety. 8,21 Although some of the key substrates 1-4 are known in the literature, 22 the presented one-pot protocol nicely supplement multistep syntheses described thus far. The final macrocyclic compounds are of our interest in the context of their potential complexing properties towards heavy-metal ions evidenced for other sulfurated crown ethers.…”

Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes

“…Initially, one equivalent of (R)-1,1Ј-binaphthyl-2,2Ј-disulfonyl dichloride (1) [12,13] and two equivalents of (S)-tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate (2) [14,15] were stirred in CH 2 Cl 2 . A new spot was observed by TLC (petroleum ether/ethyl acetate, 2:1; R f = 0.3) after 12 h; thus, the mixture was purified by column chromatography and treated with TFA.…”

Ruthenium-catalyzed synthesis of tricyclic 1,5-fused 1,2,3-triazole piperazines

“…This compound was prepared following a procedure reported for the corresponding mesylate. 47 To a solution of ( R )- 5 (1 mmol, 367 mg) in anhydrous DMF (6 mL) in 20 mL Biotage reaction vial under nitrogen, NaN 3 (2.5 mmol, 162 mg, Caution! NaN 3 is toxic, potentially explosive and should be handled with care ) was added and the solution was stirred for 5 min at room temperature, then overnight (16 h) at 60 °C.…”

Synthesis of Sulfur-Rich Crown Ethers via Azide–Alkyne Macrocyclization of α,ω-Diazido- and α,ω-Dipropargyl Sulfide Derivatives

“…In conclusion, a series of organic diazides and dithiols were prepared by modified Appel reaction and applied for the construction of a new class of sulfur-rich macrocycles 14 decorated with 1,2,3-triazole as an adjuvant complexing moiety. 8,21 Although some of the key substrates 1-4 are known in the literature, 22 the presented one-pot protocol nicely supplement multistep syntheses described thus far. The final macrocyclic compounds are of our interest in the context of their potential complexing properties towards heavy-metal ions evidenced for other sulfurated crown ethers.…”

Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes

“…Initially, one equivalent of (R)-1,1Ј-binaphthyl-2,2Ј-disulfonyl dichloride (1) [12,13] and two equivalents of (S)-tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate (2) [14,15] were stirred in CH 2 Cl 2 . A new spot was observed by TLC (petroleum ether/ethyl acetate, 2:1; R f = 0.3) after 12 h; thus, the mixture was purified by column chromatography and treated with TFA.…”

Ruthenium-catalyzed synthesis of tricyclic 1,5-fused 1,2,3-triazole piperazines

“…This compound was prepared following a procedure reported for the corresponding mesylate. 47 To a solution of ( R )- 5 (1 mmol, 367 mg) in anhydrous DMF (6 mL) in 20 mL Biotage reaction vial under nitrogen, NaN 3 (2.5 mmol, 162 mg, Caution! NaN 3 is toxic, potentially explosive and should be handled with care ) was added and the solution was stirred for 5 min at room temperature, then overnight (16 h) at 60 °C.…”

Synthesis of Sulfur-Rich Crown Ethers via Azide–Alkyne Macrocyclization of α,ω-Diazido- and α,ω-Dipropargyl Sulfide Derivatives

“…In conclusion, a series of organic diazides and dithiols were prepared by modified Appel reaction and applied for the construction of a new class of sulfur-rich macrocycles 14 decorated with 1,2,3-triazole as an adjuvant complexing moiety. 8,21 Although some of the key substrates 1-4 are known in the literature, 22 the presented one-pot protocol nicely supplement multistep syntheses described thus far. The final macrocyclic compounds are of our interest in the context of their potential complexing properties towards heavy-metal ions evidenced for other sulfurated crown ethers.…”

Synthesis of Binaphthyl Sulfonimides and Their Application in the Enantioselective Michael Addition of Ketones to Nitroalkenes

“…Initially, one equivalent of (R)-1,1Ј-binaphthyl-2,2Ј-disulfonyl dichloride (1) [12,13] and two equivalents of (S)-tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate (2) [14,15] were stirred in CH 2 Cl 2 . A new spot was observed by TLC (petroleum ether/ethyl acetate, 2:1; R f = 0.3) after 12 h; thus, the mixture was purified by column chromatography and treated with TFA.…”

Ruthenium-catalyzed synthesis of tricyclic 1,5-fused 1,2,3-triazole piperazines

“…This compound was prepared following a procedure reported for the corresponding mesylate. 47 To a solution of ( R )- 5 (1 mmol, 367 mg) in anhydrous DMF (6 mL) in 20 mL Biotage reaction vial under nitrogen, NaN 3 (2.5 mmol, 162 mg, Caution! NaN 3 is toxic, potentially explosive and should be handled with care ) was added and the solution was stirred for 5 min at room temperature, then overnight (16 h) at 60 °C.…”