56895-60-4Relevant articles and documents
Spiropyran photoswitches in the context of DNA: Synthesis and photochromic properties
Brieke, Clara,Heckel, Alexander
, p. 15726 - 15734 (2013)
A new design is presented for the incorporation of spiropyran photoswitches into nucleic acids by oligonucleotide solid phase synthesis. This design enables interaction of the 6-nitrospirobenzopyran (NitroBIPS) photoswitch with the adjacent nucleobases and leaves the photochemical properties of NitroBIPS intact. UV/Vis spectroscopy and HPLC revealed that NitroBIPS incorporated into DNA consists of up to 40 % merocyanine in its thermal equilibrium and undergoes reversible switching between the photoisomeric spiropyran (SP) and merocyanin (MC) state by alternating excitation using visible light or heat for at least fifteen switching cycles. Exchanging the chromene part of NitroBIPS on the DNA level gives access to differently substituted spiropyran derivatives allowing the screening for spiropyrans with suitable properties in a straightforward manner. Thus, by incorporating the highly hydrolysis-stable pyrido-spiropyran derivative PyBIPS pure light-triggered reversible switching of a spiropyran in DNA has been realized for the first time. Therefore, this design represents a new useful platform for investigating the photochromic behavior of different spiropyran photoswitches in a nucleic acid environment and for using spiropyrans to induce light- or heat-triggered changes in conformations or in fluorescence quenching properties of oligonucleotides. Yes, it does switch! With a new design strategy the photochemical properties of spiropyran photoswitches can be retained in DNA. Spiropyrans can be diversified on the DNA level enabling screening for spiropyrans with suitable properties in a straightforward manner (see scheme). By incorporating the highly stable spiropyran derivative PyBIPS, pure light-triggered reversible switching of a spiropyran in DNA has been realized for the first time. Copyright
An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives
Xu, Jun,Tong, Rongbiao
, p. 2952 - 2956 (2017/07/24)
An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.
Copper(I)-catalyzed cascade dearomatization of 2-substituted tryptophols with arylidonium salts
Liu, Chuan,Zhang, Wei,Dai, Li-Xin,You, Shu-Li
, p. 4525 - 4527 (2012/10/29)
Copper(I)-catalyzed dearomative arylation and vinylation of 2-substituted tryptophols were realized with a subsequent cyclization reaction. The cascade dearomatization sequence provided versatile furoindoline derivatives with two quaternary carbon centers
