204587-92-8Relevant academic research and scientific papers
Synthesis and biological evaluation of quinaldopeptin
Katayama, Katsushi,Okamura, Takuya,Sunadome, Takuya,Nakagawa, Koji,Takeda, Hiroshi,Shiro, Motoo,Matsuda, Akira,Ichikawa, Satoshi
, p. 2580 - 2590 (2014/04/17)
The second-generation total synthesis of quinaldopeptin (1) was established via a Staudinger/aza-Wittig/diastereoselective Ugi three-component reaction sequence and a racemization-free [5 + 5] coupling and macrolactamization. A single-crystal X-ray structure of the chromophore analogue 26 confirmed the structural and stereochemical assignments of the macrocycle. Synthetic 1 successfully unwound supercoiled DNA to form a relaxed DNA in a dose-dependent manner, the binding affinity of 1 to four dsODNs was within a similar range (Kb = 1.45-2.53 × 107 M-1), and the sequence selectivity was subtle. It was suggested that 1 possesses biological behaviors similar to those of sandramycin (2) in terms of cytotoxic activity against human cancer cell lines (IC50 = 3.2-12 nM) and HIF-1 inhibitory activity.
Asymmetric synthesis of anti-(2S,3S)- and syn-(2R,3S)-diaminobutanoic acid
Bunnage, Mark E.,Burke, Anthony J.,Davies, Stephen G.,Millican, Nicholas L.,Nicholson, Rebecca L.,Roberts, Paul M.,Smith, Andrew D.
, p. 3708 - 3715 (2007/10/03)
Conjugate addition of homochiral lithium N-benzyl-N-α-methylbenzylamide to tert-butyl (E)-cinnamate or tert-butyl (E)-crotonate and in situ amination with trisyl azide results in the exclusive formation of the corresponding 2-diazo-3-amino esters in >95%
