Tetraethylene glycol-derived spacer for oligonucleotide synthesis

Synthesis and Evaluation of a Series of Bis(pentylpyridinium) Compounds as Antifungal Agents

“…We have previously established that changing the counterion from bromide to chloride has no effect on the biological activity of these cationic compounds . To probe the effect of the hydrophobicity of the spacer between the headgroups, compounds 7 and 8 , in which the alkyl chain was replaced by ethylene glycol, were prepared in a similar manner from 1,11‐dibromo(tetraethylene glycol) and 1,14‐dibromo(pentaethylene glycol), respectively.…”

“…Ion-exchange chromatography was performed on Lewatit MP-64 resin (chloride form), which was swollen in H 2 O, washed with three bed volumes of 0.1 m HCl (aq) and then washed with H 2 Ou ntil the washings were neutral. Analytical RP-HPLC was performed using an XTerraRP C 18 column (5 mm, 4.6 mm ID, 250 mm) with af low rate of 0.2 mL min À1 .P reparative RP-HPLC was performed using an XTerraRP C 18 column (10 mm, 22 mm ID, 300 mm) with af low rate of 7.0 mL min À1 .1 ,11-Dibromotetraethylene glycol, [16] 1,14-dibromopenta(ethylene glycol), [17] 1,10-dihydroxydec-4,6-diyne, [22] 1,12-dihydroxydodec-5,7-diyne, [23] 1,4-bis(6'-hydroxy-1'-hexynyl)benzene, [25] 1,4-bis(5'-hydroxy-1'-pentynyl)benzene, [25] 1,4-bis(5'-hydroxypentyl)benzene, [25] 1,4-bis(6'-hydroxyhexyl)benzene, [25] 1,4-bis(6'-bromohexyl)benzene, [38] compounds 1, [14] 6, [39] 31, [19] and 32, [20] were prepared according to published methods. Detailed synthetic methods for precursors are provided in the Supporting Information.…”

“…Preparative RP‐HPLC was performed using an XTerraRP C 18 column (10 μm, 22 mm ID, 300 mm) with a flow rate of 7.0 mL min −1 . 1,11‐Dibromotetraethylene glycol, 1,14‐dibromopenta(ethylene glycol), 1,10‐dihydroxy ‐ dec‐4,6‐diyne, 1,12‐dihydroxydodec‐5,7‐diyne, 1,4‐bis(6′‐hydroxy‐1′‐hexynyl)benzene, 1,4‐bis(5′‐hydroxy‐1′‐pentynyl)benzene, 1,4‐bis(5′‐hydroxypentyl)benzene, 1,4‐bis(6′‐hydroxyhexyl)benzene, 1,4‐bis(6′‐bromohexyl)benzene, compounds 1 , 6 , 31 , and 32 , were prepared according to published methods. Detailed synthetic methods for precursors are provided in the Supporting Information.…”

Synthesis of DNA Oligomers Possessing a Covalently Cross‐Linked Watson–Crick Base Pair Model

“…In the case of H ‐type oligomer syntheses, the column containing the solid support was removed from the synthesizer twice (after completion of the second and third chain elongations), subjected to Lev and Alloc deprotections on the solid support,7, 8 and reintroduced into the synthesizer to complete the third and fourth chain elongations, steps 12 and 17. The overall efficiencies of these syntheses are summarized in the Experimental Section and demonstrate that the CH 2 ‐bridged base pair models 1 a – c and 2 a – c could be efficiently incorporated into n ‐, h ‐, and H ‐type oligomers 13…”

High-Yield Immobilization of a Puromycin Analogue for the Solid Support Synthesis of Aminoacyl-tRNA Fragments

“…In addition to the succinate linkage, we also used a commercially available poly(ethylene glycol)-derived linker/spacer: 3,6,9-trioxaundecanoic diacid. We have shown that a similar spacer used for the solid support of oligonucleotides proved to be superior in terms of both coupling yields and homogeneity of the final product, when compared to several other tested spacer molecules of up to double its length …”