201275-55-0Relevant academic research and scientific papers
Spongistatin synthetic studies. 2. Assembly of the C(18-28) spiroketal
Smith III, Amos B.,Zhuang, Linghang,Brook, Christopher S.,Lin, Qiyan,Moser, William H.,Lee Trout, Robert E.,Boldi, Armen M.
, p. 8671 - 8674 (1997)
The C(18-28) CD-ring spiroketal subunit of the spongistatins, marine polyether macrolides with unprecedented antitumor activity, has been generated via a highly convergent and completely stereocontrolled sequence. Key operations include a one-flask dithiane bisalkylation and a metal-assisted spiroketal equilibration.
Furan-oxidation-triggered inducible DNA cross-linking: Acyclic versus cyclic furan-containing building blocks - On the benefit of restoring the cyclic sugar backbone
Stevens, Kristof,Claeys, Diederica D.,Catak, Saron,Figaroli, Sara,Hocek, Michal,Tromp, Jan M.,Schuerch, Stefan,Speybroeck, Veronique Van,Madder, Annemieke
supporting information; experimental part, p. 6940 - 6953 (2011/07/30)
Oligodeoxynucleotides incorporating a reactive functionality can cause irreversible cross-linking to the target sequence and have been widely studied for their potential in inhibition of gene expression or development of diagnostic probes for gene analysi
Spongipyran synthetic studies. Total synthesis of (+)-spongistatin 2
Smith III, Amos B.,Lin, Qiyan,Doughty, Victoria A.,Zhuang, Linghang,McBriar, Mark D.,Kerns, Jeffrey K.,Boldi, Armen M.,Murase, Noriaki,Moser, William H.,Brook, Christopher S.,Bennett, Clay S.,Nakayama, Kiyoshi,Sobukawa, Masao,Lee Trout, Robert E.
supporting information; experimental part, p. 6470 - 6488 (2011/02/25)
Evolution of a convergent synthetic strategy to access (+)-spongistatin 2 (2), a potent cytotoxic marine macrolide, is described. Highlights of the synthesis include: development of a multicomponent dithiane-mediated linchpin union tactic, devised and implemented specifically for construction of the spongistatin AB and CD spiro ring systems; application of a CaII ion controlled acid promoted equilibration to set the thermodynamically less stable axial-equatorial stereogenicity in the CD spiroketal; use of sulfone addition/Julia methylenation sequences to unite the AB and CD fragments and introduce the C(44)-C(51) side chain; and fragment union and final elaboration to (+)-spongistatin 2 (2) exploiting Wittig olefination to unite the advanced ABCD and EF fragments, followed by regioselective Yamaguchi macrolactonization and global deprotection. Correction of the CD spiro ring stereogenicity was subsequently achieved via acid equilibration in the presence of CaII ion to furnish (+)-spongistatin 2 (2). The synthesis proceeded with a longest linear sequence of 41 steps.
Twisted intercalating nucleic acids - Intercalator influence on parallel triplex stabilities
Filichev, Vyacheslav V.,Gaber, Hatem,Olsen, Thomas R.,Jorgensen, Per T.,Jessen, Carsten H.,Pedersen, Erik B.
, p. 3960 - 3968 (2007/10/03)
Phosphoramidites of several new twisted intercalating nucleic acid (TINA) monomers and the previously discovered (R)-1-O-[4-(1-pyrenylethynyl) phenylmethyl]glycerol (1) were synthesized and used in DNA synthesis. Stabilization of Hoogsteen-type triplexes was observed in cases of insertion of the novel (R)-1-O-[3-(naphthalen-1-ylethynyl)phenylmethyl]glycerol (2) as a bulge into homopyrimidine oligodeoxynucleotides (ONs), whereas phenylethynyl and 4-(biphenylylethynyl) derivatives of TINAs resulted in destabilization of parallel triplexes relative to the wild-type triplex. It was concluded that TINA monomers should possess at least two fused phenyl rings attached through the triple bond at the 4-position of bulged (R)-1-O-(phenylmethyl)glycerol in homopyrimidine ONs in order to stabilize parallel triplexes. Slight destabilization of DNA/DNA Watson-Crick type duplexes (ΔTm = 1.0-4.5°C) was detected for 2 inserted as a bulge, while RNA/DNA duplexes and duplexes with other TINA analogues were considerably destabilized (ΔTm > 6.0°C). In cases of double insertion of 1 opposite to base inversions in dsDNA, the thermal stabilities of the triplexes were higher than that of the wild-type triplex, which is a new solution to overcome the problem of targeting homopurine stretches with single base pair inversions. A DNA three-way junction was considerably stabilized (ΔT m in a range of 10.0-15.5°C) upon insertion of TINA monomers in the junction point as a bulge. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
