Tetrahedron p. 14957 - 14974 (1997)
Update date:2022-09-26
Topics:
Ceulemans, Griet
Van Aerschot, Arthur
Rozenski, Jef
Herdewijn, Piet
Fully modified oligonucleotides were synthesised from the 3-O-phosphoramidites of monomethoxytritylated trans-3-hydroxy-N-[(N6-benzoyladenin-9-yl)-acetyl]-prolinol [(2S,3R) and (2R,3S) series], trans-3-hydroxy-N-[(thymin-1-yl)-acetyl]-prolinol [(2S,3R) and (2R,3S) series], and cis-3-hydroxy-N-[(N6-benzoyl-adenin-9-yl)-acetyl]-L-prolinol (2R,3R). Remarkably, as well the L-trans (2R,3S) as the D-trans (2S,3R) all-adenine oligonucleotides are capable of hybridisation with complementary DNA and RNA. With modified all-thymine trans-oligomers no complexation with natural nucleic acids was observed. However, complex formation between two modified strands of the same sense of chirality does occur with formation of a triple stranded complex. The all-thymine oligonucleotides with trans-3-HO-N-acetylprolinol backbone are capable of hybridisation with trans-4-HO-N-acetylprolinol oligoadenylates of the same enantiomeric form in both the D and the L series, and inversely, the all-adenine oligonucleotide with the trans-3-HO conformation hybridises with the trans-4-HO oligothymidylates. While the former interactions have a triple stranded origin, the latter are 1:1 interactions. No interactions were noticed upon mixing oligonucleotide analogues of different sense of chirality. Modified mixed trans-3-HO A,T sequences display no hybridisation with complementary nucleic acids, nor homocomplex formation. The L-cis all-adenine oligonucleotide hybridises with its RNA complement. Several complexes were investigated by circular dichroism and microcalorimetry. In conclusion, the 3-hydroxy-N-acetylprolinol system represents an example of homochiral oligonucleotides built up from two enantiomeric forms and hybridizing both with natural nucleic acids.
View MoreTianjin Realet Chemical Technology Co.,Ltd.
website:http://www.realetchem.com
Contact:+86-022-58788819
Address:shuanggang industrial park
Xuzhou Tianrun Chemical Co.,Ltd
website:http://www.tianrunchem.cn
Contact:86-516-83832636
Address:fuxing road
Hangzhou yi lu biont technology Co., LTD
Contact:+86-571-88152630
Address:Hangzhoushi HuafengRoad Yicheng3Building1001room.
Contact:+1-973-357-0577
Address:10 Taft Rd.
PharmaResources(Kaiyuan)CO,.Ltd
Contact:+86-21-50720028
Address:No.3, Beihuan Road, Economic Development District, Kaiyuan City, Tieling City, Liaoning Province, China 112300
Doi:10.1055/s-0034-1380463
(2015)Doi:10.1021/ja211389g
(2012)Doi:10.1002/adsc.201900142
(2019)Doi:10.1021/jm2013216
(2012)Doi:10.1016/j.bmc.2009.11.013
(2010)Doi:10.1016/j.jorganchem.2011.11.034
(2012)